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M e t h a d o n e - D r u g B a n k h t t p s : / / w w w . d r u g b a n k .

c a / d r u g s / D B 0 0 3 3 3

Identification Pharmacology Interactions References ADMET Pharmacoeconomics Properties Spectra Taxonomy 3 Comments

Targets (5) Enzymes (11) Transporters (1) Biointeractions (20) (/drugs/DB00333/biointeractions) Show Drugs with Similar Structures

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Identification

Name Methadone

Accession Number DB00333 (APRD00485)

Type Small Molecule

Groups Approved

Description A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of morphine. It also has a
depressant action on the cough center and may be given to control intractable cough associated with terminal lung cancer. Methadone is also used as part of the treatment of
dependence on opioid drugs, although prolonged use of methadone itself may result in dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). In Australia
methadone is a Schedule 8 (controlled) drug.

Structure

H3 C
O

H3 C
N
(/structures/DB00333/image.svg)
CH3
CH3

MOL (/structures/small_molecule_drugs/DB00333.mol) SDF (/structures/small_molecule_drugs/DB00333.sdf) 3D-SDF (/structures/small_molecule_drugs/DB00333.sdf?dim=3d)

PDB (/structures/small_molecule_drugs/DB00333.pdb) SMILES (/structures/small_molecule_drugs/DB00333.smiles) InChI (/structures/small_molecule_drugs/DB00333.inchi)

View 3D Structure (/structures/small_molecule_drugs/DB00333)

Synonyms (+-)-Methadone

(+/-)-Methadone

()-methadone

6-Dimethylamino-4,4-diphenyl-3-heptanone

dl-Methadone

Methadonum

External Identifiers Not Available

Approved Show 10 entries Search


Prescription
Products Marketing Marketing
Name Dosage Strength Route Labeller Start End

Diskets Tablet 40 mg/1 Oral West Ward Pharmaceuticals Corp. 1973-03-14 Not applicable

Dolophine Tablet 5 mg/1 Oral West Ward Pharmaceuticals Corp. 1947-08-13 Not applicable

Dolophine Tablet 10 mg/1 Oral West Ward Pharmaceuticals Corp. 1947-08-13 Not applicable

Dolophine Tablet 10 mg/1 Oral Pd Rx Pharmaceuticals, Inc. 2010-01-01 Not applicable


Hydrochloride

Dolophine Tablet 5 mg/1 Oral Pd Rx Pharmaceuticals, Inc. 2010-01-01 Not applicable


Hydrochloride

Metadol Tablet 25 mg Oral Paladin Labs Inc 2003-07-29 Not applicable

Metadol Solution 1 mg Oral Paladin Labs Inc 2003-07-11 Not applicable

Metadol Liquid 10 mg Oral Paladin Labs Inc 2000-05-05 Not applicable

Metadol Tablet 1 mg Oral Paladin Labs Inc 2003-07-29 Not applicable

Metadol Tablet 5 mg Oral Paladin Labs Inc 2003-07-29 Not applicable

Showing 1 to 10 of 37 entries Previous 1 2 3 4 Next

1 d a r i 1 3 1 2 / 6 / 2 0 1 6 9 : 0 6 P M
Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

Approved Generic Show 10 entries Search


Prescription
Products Marketing Marketing
Name Dosage Strength Route Labeller Start End

Methadone Tablet 10 mg/1 Oral Lake Erie Medical DBA Quality Care Products LLC 2010-10-11 Not applicable
Hydrochloride

Methadone Tablet 10 mg/1 Oral Ascend Laboratories, LLC 2012-01-16 Not applicable
Hydrochloride

Methadone Tablet 10 mg/1 Oral Major Pharmaceuticals 2012-01-16 Not applicable


Hydrochloride

Methadone Tablet 10 mg/1 Oral Mc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation 2012-01-16 Not applicable
Hydrochloride

Methadone Concentrate 10 mg/mL Oral West Ward Pharmaceuticals Corp. 1988-09-06 Not applicable
Hydrochloride

Methadone Tablet 10 mg/1 Oral Physicians Total Care, Inc. 2004-01-07 Not applicable
Hydrochloride

Methadone Solution 10 mg/5mL Oral Vista Pharm Inc 2010-08-01 Not applicable
Hydrochloride

Methadone Tablet 10 mg/1 Oral Mallinckrodt, Inc. 2009-05-19 Not applicable


Hydrochloride

Methadone Tablet 10 mg/1 Oral Aurolife Pharma, LLC 2015-09-15 Not applicable
Hydrochloride

Methadone Tablet 10 mg/1 Oral American Health Packaging 2014-10-02 Not applicable
Hydrochloride

Showing 1 to 10 of 36 entries Previous 1 2 3 4 Next

Approved Over the Not Available


Counter Products

Unapproved/Other Not Available


Products

International Show 10 entries Search


Brands
Name Company

Adolan Not Available

Depridol Not Available

Heptadon Not Available

Heptanon Not Available

Ketalgin Not Available

Mephenon Not Available

Physeptone Not Available

Polamidon Not Available

Showing 1 to 8 of 8 entries Previous 1 Next

Brand mixtures Not Available

Salts Name/CAS Structure Properties

Methadone Hydrochloride (/salts InChI Key: FJQXCDYVZAHXNS- DBSALT000346 (/salts/DBSALT000346)


/DBSALT000346) UHFFFAOYNA-N
1095-90-5 Monoisotopic Mass: 345.18594223
(/structures Average Mass: 345.906

/DBSALT000346/image.png)

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Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

Categories Analgesics (/categories/DBCAT000041)


Analgesics, Opioid (/categories/DBCAT000480)
Antiemetics Antagonists (/categories/DBCAT002669)
Antitussive Agents (/categories/DBCAT000738)
Central Nervous System Agents (/categories/DBCAT000044)
Central Nervous System Depressants (/categories/DBCAT000399)
Combined Inhibitors of CYP3A4 and P-glycoprotein (/categories/DBCAT002747)
Cytochrome P-450 CYP1A2 Substrates (/categories/DBCAT002609)
Cytochrome P-450 CYP2B6 Substrates (/categories/DBCAT002619)
Cytochrome P-450 CYP2C19 Substrates (/categories/DBCAT002638)
Cytochrome P-450 CYP2C8 Substrates (/categories/DBCAT002642)
Cytochrome P-450 CYP2C9 Substrates (/categories/DBCAT002634)
Cytochrome P-450 CYP2D6 Inhibitors (/categories/DBCAT000911)
Cytochrome P-450 CYP2D6 Inhibitors (moderate) (/categories/DBCAT002625)
Cytochrome P-450 CYP2D6 Substrates (/categories/DBCAT002623)
Cytochrome P-450 CYP3A Inducers (/categories/DBCAT000492)
Cytochrome P-450 CYP3A Inhibitors (/categories/DBCAT000934)
Cytochrome P-450 CYP3A4 Substrates (/categories/DBCAT002646)
Diphenylpropylamine Derivatives (/categories/DBCAT002316)
Drugs Used in Addictive Disorders (/categories/DBCAT002183)
Drugs Used in Opioid Dependence (/categories/DBCAT002315)
Ketones (/categories/DBCAT000720)
Moderate Risk QTc-Prolonging Agents (/categories/DBCAT002690)
Narcotics (/categories/DBCAT000479)
Nervous System (/categories/DBCAT002148)
Organic Chemicals (/categories/DBCAT000250)
P-glycoprotein/ABCB1 Inhibitors (/categories/DBCAT002667)
Peripheral Nervous System Agents (/categories/DBCAT000043)
Respiratory System Agents (/categories/DBCAT000132)
Sensory System Agents (/categories/DBCAT000042)
Serotonin Modulators (/categories/DBCAT002706)

UNII UC6VBE7V1Z (http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=UC6VBE7V1Z)

CAS number 76-99-3

Weight Average: 309.4452


Monoisotopic: 309.209264491

Chemical Formula C21H27NO

InChI Key USSIQXCVUWKGNF-UHFFFAOYSA-N

InChI InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3

IUPAC Name 6-(dimethylamino)-4,4-diphenylheptan-3-one

SMILES CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication For the treatment of dry cough, drug withdrawal syndrome, opioid type drug dependence, and pain.

Structured Opioid type dependence (/indications/DBCOND0020938)


Indications PAIN (/indications/DBCOND0033990)

Pharmacodynamics Methadone is a synthetic opioid analgesic with multiple actions quantitatively similar to those at morphine, the most prominent of which involve the central nervous syste m and
organs composed of smooth muscle. However, Methadone is more active and more toxic than morphine. Methadone is indicated for relief of severe pain, for detoxification treatment
of narcotic addiction, and for temporary maintenance treatment of narcotic addiction. The principal actions of therapeutic value are analgesia and sedation and detoxifica tion or
temporary maintenance in narcotic addiction. The Methadone abstinence syndrome, although qualitatively similar to that of morphine, differs in that the onset is slower, t he course is
more prolonged, and the symptoms are less severe.

Mechanism of Methadone is a mu-agonist; a synthetic opioid analgesic with multiple actions qualitatively similar to those of morphine, the most prominent of which involves the central nervous
action system and organs composed of smooth muscle. The principal therapeutic uses for methadone are for analgesia and for detoxification or maintenance in opioid addiction. The
methadone abstinence syndrome, although qualitatively similar to that of morphine, differs in that the onset is slower, the course is more prolonged, and the symptoms are less
severe. Some data also indicate that methadone acts as an antagonist at the N-methyl-D-aspartate (NMDA) receptor. The contribution of NMDA receptor antagonism to
methadone's efficacy is unknown. Other NMDA receptor antagonists have been shown to produce neurotoxic effects in animals.

Target Kind Pharmacological action Actions Organism UniProt ID

Mu-type opioid receptor Protein yes agonist Human P35372 (http://www.uniprot.org/uniprot/P35372) details

Glutamate receptor ionotropic, NMDA 3A Protein yes antagonist Human Q8TCU5 (http://www.uniprot.org/uniprot/Q8TCU5) details

Neuronal acetylcholine receptor subunit alpha-10 Protein yes antagonist Human Q9GZZ6 (http://www.uniprot.org/uniprot/Q9GZZ6) details

Delta-type opioid receptor Protein yes agonist Human P41143 (http://www.uniprot.org/uniprot/P41143) details

5-hydroxytryptamine receptor 3A Protein unknown antagonist Human P46098 (http://www.uniprot.org/uniprot/P46098) details

Related Articles Prodrug Analgesics: More (or Less) Than Expected? Methadone Maintenance Therapy for Opioid Addiction
Gayle Nicholas Scott, PharmD, Medscape , 2013 Julia Lowe Behr, Rn, Msn, Aprn, Clinician Reviews

Drug Interactions in Palliative Care Adult Cancer Pain: Part 2 -- The Latest Guidelines for Pain Management
Stephen A. Bernard et al., Journal of Clinical Oncology , 2000 Laura A. Stokowski, RN, MS, Medscape , 2010

Methadone Is Most Often Prescribed in the Hospital for Noncancer Pain by Palliative Health
Providers
PracticeUpdate , 2016

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Absorption Well absorbed following oral administration. The bioavailability of methadone ranges between 36 to 100%.

Volume of 1.0 to 8.0 L/kg


distribution

Protein binding In plasma, methadone is predominantly bound to 1-acid glycoprotein (85% to 90%).

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Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

Metabolism Hepatic. Cytochrome P450 enzymes, primarily CYP3A4, CYP2B6, and CYP2C19 and to a lesser extent CYP2C9 and CYP2D6, are responsible for conversion of methadone to
EDDP and other inactive metabolites, which are excreted mainly in the urine.

Substrate Enzymes Product

Methadone 2-Ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) Details (/reactions/182)


Cytochrome P450 2D6 (/biodb (/metabolites/DBMET00181)
/bio_entities/BE0002363)
Cytochrome P450 3A4 (/biodb
/bio_entities/BE0002638)
Cytochrome P450 2B6 (/biodb
/bio_entities/BE0003549)
Cytochrome P450 2C8 (/biodb
/bio_entities/BE0002887)
Cytochrome P450 2C19 (/biodb
/bio_entities/BE0003536)
Cytochrome P450 3A7 (/biodb
/bio_entities/BE0003612)

2-Ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) 2-Ethyl-5-methyl-3,3-diphenyl-1-pyrroline (EMDP) Details (/reactions/1155)


(/metabolites/DBMET00181) Cytochrome P450 3A7 (/biodb (/metabolites/DBMET01087)
/bio_entities/BE0003612)

Route of The elimination of methadone is mediated by extensive biotransformation, followed by renal and fecal excretion. Unmetabolized methadone and its metabolites are excreted in urine
elimination to a variable degree.

Half life 24-36 hours

Clearance 1.4 to 126 L/h

Toxicity In severe overdosage, particularly by the intravenous route, apnea, circulatory collapse, cardiac arrest, and death may occur.

Affected organisms Humans and other mammals

Pathways Pathway Category SMPDB ID

Methadone Metabolism Pathway Drug metabolism SMP00624 (http://smpdb.ca/view/SMP00624?highlight[compounds][]=DB00333&highlight[proteins][]=DB00333)

Methadone Action Pathway Drug action SMP00408 (http://smpdb.ca/view/SMP00408?highlight[compounds][]=DB00333&highlight[proteins][]=DB00333)

SNP Mediated Not Available


Effects

SNP Mediated Not Available


Adverse Drug
Reactions

Interactions

Drug Interactions Show 10 entries Search

Drug Interaction Drug group

1,1,1,2 Tetrafluoroethane The risk or severity of adverse effects can be increased when Methadone is combined with 1,1,1,2 Investigational
Tetrafluoroethane.

2,5-Dimethoxy-4-ethylamphetamine 2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Methadone. Experimental, Illicit
(/drugs/DB01467)

3,4-Methylenedioxyamphetamine 3,4-Methylenedioxyamphetamine may increase the analgesic activities of Methadone. Experimental, Illicit
(/drugs/DB01509)

3,4-Methylenedioxymethamphetamine 3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Methadone. Experimental, Illicit
(/drugs/DB01454)

4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Methadone. Experimental, Illicit
(/drugs/DB01484)

4-Methoxyamphetamine (/drugs The metabolism of 4-Methoxyamphetamine can be decreased when combined with Methadone. Experimental, Illicit
/DB01472)

7-Nitroindazole (/drugs/DB02207) The risk or severity of adverse effects can be increased when Methadone is combined with 7-Nitroindazole. Experimental

7,8-DICHLORO-1,2,3,4- The risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4- Experimental
TETRAHYDROISOQUINOLINE TETRAHYDROISOQUINOLINE is combined with Methadone.
(/drugs/DB08550)

Abacavir (/drugs/DB01048) The therapeutic efficacy of Abacavir can be decreased when used in combination with Methadone. Approved, Investigational

Abiraterone (/drugs/DB05812) The serum concentration of Methadone can be increased when it is combined with Abiraterone. Approved

Showing 1 to 10 of 889 entries Previous 1 2 3 4 5 89 Next

Food Interactions Take without regard to meals. Avoid alcohol. Usually diluted in fruit juice.

References

Synthesis Charles J. Barnett, Modification of methadone synthesis process step. U.S. Patent US4048211, issued August, 1952.
Reference
US4048211 (https://www.google.com/?tbm=pts#q=4048211&tbm=pts)

General References 1. Kell MJ: Utilization of plasma and urine methadone concentrations to optimize treatment in maintenance clinics: I. Measurement techniques for a clinical setting. J Addict Dis. 1994;13(1):5-26.
[PubMed:8018740 (http://www.ncbi.nlm.nih.gov/pubmed/8018740)]
2. Eap CB, Buclin T, Baumann P: Interindividual variability of the clinical pharmacokinetics of methadone: implications for the treatment of opioid dependence. Clin Pharmaco kinet. 2002;41(14):1153-93.
[PubMed:12405865 (http://www.ncbi.nlm.nih.gov/pubmed/12405865)]
3. Joseph H, Stancliff S, Langrod J: Methadone maintenance treatment (MMT): a review of historical and clinical issues. Mt Sinai J Med. 2000 Oct-Nov;67(5-6):347-64.
[PubMed:11064485 (http://www.ncbi.nlm.nih.gov/pubmed/11064485)]
4. Connock M, Juarez-Garcia A, Jowett S, Frew E, Liu Z, Taylor RJ, Fry-Smith A, Day E, Lintzeris N, Roberts T, Burls A, Taylor RS: Methadone and buprenorphine for the manage ment of opioid dependence:
a systematic review and economic evaluation. Health Technol Assess. 2007 Mar;11(9):1-171, iii-iv. [PubMed:17313907 (http://www.ncbi.nlm.nih.gov/pubmed/17313907)]
5. Donny EC, Brasser SM, Bigelow GE, Stitzer ML, Walsh SL: Methadone doses of 100 mg or greater are more effective than lower doses at suppressing heroin self-administration in opioid-dependent
volunteers. Addiction. 2005 Oct;100(10):1496-509. [PubMed:16185211 (http://www.ncbi.nlm.nih.gov/pubmed/16185211)]

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Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

External Links Resource Link

KEGG Compound C07163 (http://www.genome.jp/dbget-bin/www_bget?cpd:C07163)

PubChem Compound 4095 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4095)

PubChem Substance 46505722 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505722)

ChemSpider 3953 (http://www.chemspider.com/Chemical-Structure.3953.html)

ChEBI 6807 (http://www.ebi.ac.uk/chebi/searchId.do?chebiId=6807)

ChEMBL CHEMBL651 (http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL651)

Therapeutic Targets Database DAP000267 (http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000267)

PharmGKB PA450401 (http://www.pharmgkb.org/drug/PA450401)

Drug Product Database 6417 (http://webprod5.hc-sc.gc.ca/dpd-bdpp/info.do?code=6417&lang=eng)

RxList http://www.rxlist.com/cgi/generic/methdone.htm (http://www.rxlist.com/cgi/generic/methdone.htm)

Drugs.com http://www.drugs.com/methadone.html (http://www.drugs.com/methadone.html)

Wikipedia Methadone (http://en.wikipedia.org/wiki/Methadone)

ATC Codes N07BC02


N07BC Drugs used in opioid dependence (/atc/N07BC)
N07B DRUGS USED IN ADDICTIVE DISORDERS (/atc/N07B)
N07 OTHER NERVOUS SYSTEM DRUGS (/atc/N07)
N NERVOUS SYSTEM (/atc/N)
N02AC52
N02AC Diphenylpropylamine derivatives (/atc/N02AC)
N02A OPIOIDS (/atc/N02A)
N02 ANALGESICS (/atc/N02)
N NERVOUS SYSTEM (/atc/N)

AHFS Codes 28:08.08

PDB Entries Not Available

FDA label Download (https://s3-us-west-2.amazonaws.com/drugbank/fda_labels/DB00333.pdf?1265922805) (327 KB)

MSDS Download (https://s3-us-west-2.amazonaws.com/drugbank/msds/DB00333.pdf?1265922743) (60 KB)

ADMET

Predicted ADMET Property Value Probability


features
Human Intestinal Absorption + 0.9968

Blood Brain Barrier + 0.9772

Caco-2 permeable + 0.7841

P-glycoprotein substrate Substrate 0.6224

P-glycoprotein inhibitor I Inhibitor 0.7627

P-glycoprotein inhibitor II Non-inhibitor 0.9101

Renal organic cation transporter Non-inhibitor 0.5851

CYP450 2C9 substrate Non-substrate 0.7822

CYP450 2D6 substrate Non-substrate 0.7743

CYP450 3A4 substrate Substrate 0.66

CYP450 1A2 substrate Inhibitor 0.5312

CYP450 2C9 inhibitor Non-inhibitor 0.864

CYP450 2D6 inhibitor Inhibitor 0.5449

CYP450 2C19 inhibitor Non-inhibitor 0.8177

CYP450 3A4 inhibitor Non-inhibitor 0.5507

CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6586

Ames test Non AMES toxic 0.946

Carcinogenicity Carcinogens 0.6315

Biodegradation Not ready biodegradable 0.9888

Rat acute toxicity 3.5250 LD50, mol/kg Not applicable

hERG inhibition (predictor I) Weak inhibitor 0.947

hERG inhibition (predictor II) Inhibitor 0.7606

ADMET data is predicted using admetSAR (http://lmmd.ecust.edu.cn:8000), a free tool for evaluating chemical ADMET properties.
(23092397 (http://www.ncbi.nlm.nih.gov/pubmed/23092397))

Pharmacoeconomics

Manufacturers Roxane laboratories inc


Vistapharm inc
Mallinckrodt chemical inc
Bioniche pharma usa llc
Sandoz inc
Mallinckrodt inc
The pharmanetwork llc

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Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

Packagers AAIPharma Inc. (http://www.aaipharma.com)


Bioniche Pharma (http://www.bionichepharmausa.com)
Blenheim Pharmacal (http://www.bpipack.com)
Bryant Ranch Prepack (http://bryantranchprepack.com)
D.M. Graham Laboratories Inc.
Direct Dispensing Inc.
Dispensing Solutions (http://www.drxdispensing.com)
Diversified Healthcare Services Inc. (http://www.dhscorp.com)
Eon Labs
Lake Erie Medical and Surgical Supply
Mallinckrodt Inc. (http://www.mallinckrodt.com)
Nucare Pharmaceuticals Inc. (http://www.nucarerx.com)
Physicians Total Care Inc. (http://www.physicianstotalcare.com)
Redpharm Drug
Roxane Labs (http://www.roxane.com)
Stat Rx Usa (http://statrxusa.exporterus.com)
Vistapharm Inc. (http://www.vistapharm.com)
Xanodyne Pharmaceuticals Inc. (http://www.xanodyne.com)

Dosage forms Show 10 entries Search

Form Route Strength

Liquid Oral 10 mg

Tablet Oral 1 mg

Tablet Oral 10 mg

Tablet Oral 25 mg

Tablet Oral 5 mg

Solution Oral 1 mg

Injection, solution Intramuscular; Intravenous; Subcutaneous 10 mg/mL

Powder Oral 1 g/g

Solution Oral 10 mg/5mL

Solution Oral 5 mg/5mL

Showing 1 to 10 of 15 entries Previous 1 2 Next

Prices Show 10 entries Search

Unit description Cost Unit

Methadone hcl 10 mg/ml vial 7.48USD ml

Methadone hcl powder 5.91USD g

Metadol 25 mg Tablet 1.69USD tablet

Metadol 10 mg Tablet 0.9USD tablet

Methadone intensol 10 mg/ml 0.85USD ml

Metadol 5 mg Tablet 0.56USD tablet

Methadone hcl 10 mg tablet 0.37USD tablet

Metadol Concentrate 10 mg/ml Liquid 0.37USD ml

Methadone hcl 5 mg tablet 0.34USD tablet

Dolophine hcl 10 mg tablet 0.21USD tablet

Showing 1 to 10 of 15 entries Previous 1 2 Next

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents Not Available

Properties

State Solid

Experimental Property Value Source


Properties
melting point 235.0 C Not Available

logP 3.93 HANSCH,C ET AL. (1995)

pKa 8.94 (at 25 C) PERRIN,DD (1965)

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Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

Predicted Property Value Source


Properties
Water Solubility 0.0059 mg/mL ALOGPS (http://www.vcclab.org/lab/alogps/)

logP 4.14 ALOGPS (http://www.vcclab.org/lab/alogps/)

logP 5.01 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#logp_logd)

logS -4.7 ALOGPS (http://www.vcclab.org/lab/alogps/)

pKa (Strongest Acidic) 18.78 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

pKa (Strongest Basic) 9.12 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

Physiological Charge 1 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

Hydrogen Acceptor Count 2 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)

Hydrogen Donor Count 0 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)

Polar Surface Area 20.31 2 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topolgical_surface)

Rotatable Bond Count 7 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)

Refractivity 97.27 m3mol-1 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#refractivity)

Polarizability 36.29 3 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Number of Rings 2 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)

Bioavailability 1 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Rule of Five Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Ghose Filter Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Veber's Rule Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

MDDR-like Rule Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Spectra

Mass Spec (NIST) Not Available

Spectra Spectrum Splash Key


Type Description (http://splash.fiehnlab.ucdavis.edu/)

Predicted Predicted Not Available


LC-MS/MS LC-MS/MS
Spectrum -
10V,
Positive
(/spectra
/ms_ms
/70542)

Predicted Predicted Not Available


LC-MS/MS LC-MS/MS
Spectrum -
20V,
Positive
(/spectra
/ms_ms
/70543)

Predicted Predicted Not Available


LC-MS/MS LC-MS/MS
Spectrum -
40V,
Positive
(/spectra
/ms_ms
/70544)

Predicted Predicted Not Available


LC-MS/MS LC-MS/MS
Spectrum -
10V,
Negative
(/spectra
/ms_ms
/129060)

Predicted Predicted Not Available


LC-MS/MS LC-MS/MS
Spectrum -
20V,
Negative
(/spectra
/ms_ms
/129061)

Predicted Predicted Not Available


LC-MS/MS LC-MS/MS
Spectrum -
40V,
Negative
(/spectra
/ms_ms
/129062)

MS Mass splash10-00di- View in MoNA (http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-9210000000-7542d8c3f742c7713c13)


Spectrum 9210000000-7542d8c3f742c7713c13
(Electron
Ionization)
(/spectra
/ei_ms/276)

Taxonomy

Description This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane
wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom Organic compounds (http://classyfire.wishartlab.com/tax_nodes/C0000000)

Super Class Benzenoids (http://classyfire.wishartlab.com/tax_nodes/C0002448)

7 dari 13 12/6/2016 9:06 PM


Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

Class Benzene and substituted derivatives (http://classyfire.wishartlab.com/tax_nodes/C0002279)

Sub Class Diphenylmethanes (http://classyfire.wishartlab.com/tax_nodes/C0000369)

Direct Parent Diphenylmethanes (http://classyfire.wishartlab.com/tax_nodes/C0000369)

Alternative Parents Phenylpropylamines (http://classyfire.wishartlab.com/tax_nodes/C0000187)


Aralkylamines (http://classyfire.wishartlab.com/tax_nodes/C0003899)
Gamma-amino ketones (http://classyfire.wishartlab.com/tax_nodes/C0001118)
Trialkylamines (http://classyfire.wishartlab.com/tax_nodes/C0002239)
Hydrocarbon derivatives (http://classyfire.wishartlab.com/tax_nodes/C0004150)

Substituents Diphenylmethane
Phenylpropylamine
Aralkylamine
Gamma-aminoketone
Tertiary aliphatic amine
Tertiary amine
Ketone
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic homomonocyclic compound

Molecular Aromatic homomonocyclic compounds


Framework

External Not Available


Descriptors

Targets

1. Mu-type opioid receptor (/biodb/polypeptides/P35372) Details (/biodb/polypeptides/P35372)

Kind Protein
Organism Human
Pharmacological action yes
Actions agonist

General Function: Voltage-gated calcium channel activity


Specific Function: Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl,
etorphine, buprenorphin and methadone. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent
exchange of GDP for GTP in the G-protein alpha subunit leading to dissociati...
Gene Name: OPRM1
Uniprot ID: P35372 (http://www.uniprot.org/uniprot/P35372)
Molecular Weight: 44778.855 Da

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 (http://www.ncbi.nlm.nih.gov/pubmed/17139284)]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 (http://www.ncbi.nlm.nih.gov/pubmed/17016423)]
3. Shi J, Hui L, Xu Y, Wang F, Huang W, Hu G: Sequence variations in the mu-opioid receptor gene (OPRM1) associated with human addiction to heroin. Hum Mutat. 2002 Apr;19(4) :459-60.
[PubMed:11933204 (http://www.ncbi.nlm.nih.gov/pubmed/11933204)]
4. Kakko J, von Wachenfeldt J, Svanborg KD, Lidstrom J, Barr CS, Heilig M: Mood and neuroendocrine response to a chemical stressor, metyrapone, in buprenorphine-maintained h eroin dependence. Biol Psychiatry.
2008 Jan 15;63(2):172-7. Epub 2007 Sep 11. [PubMed:17850768 (http://www.ncbi.nlm.nih.gov/pubmed/17850768)]
5. Kvam TM, Baar C, Rakvag TT, Kaasa S, Krokan HE, Skorpen F: Genetic analysis of the murine mu opioid receptor: increased complexity of Oprm gene splicing. J Mol Med (Berl) . 2004 Apr;82(4):250-5. Epub 2004
Jan 9. [PubMed:14991152 (http://www.ncbi.nlm.nih.gov/pubmed/14991152)]

2. Glutamate receptor ionotropic, NMDA 3A (/biodb/polypeptides/Q8TCU5) Details (/biodb/polypeptides/Q8TCU5)

Kind Protein
Organism Human
Pharmacological action yes
Actions antagonist

General Function: Protein phosphatase 2a binding


Specific Function: NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to
magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism (By
similarity).
Gene Name: GRIN3A
Uniprot ID: Q8TCU5 (http://www.uniprot.org/uniprot/Q8TCU5)
Molecular Weight: 125464.07 Da

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 (http://www.ncbi.nlm.nih.gov/pubmed/17139284)]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 (http://www.ncbi.nlm.nih.gov/pubmed/17016423)]
3. Sotgiu ML, Valente M, Storchi R, Caramenti G, Biella GE: Cooperative N-methyl-D-aspartate (NMDA) receptor antagonism and mu-opioid receptor agonism mediate the methadone inhibition of the spinal neuron
pain-related hyperactivity in a rat model of neuropathic pain. Pharmacol Res. 2009 Oct;60(4):284-90. doi: 10.1016/j.phrs.2009.04.002. Epub 2009 Apr 11.
[PubMed:19717013 (http://www.ncbi.nlm.nih.gov/pubmed/19717013)]

3. Neuronal acetylcholine receptor subunit alpha-10 (/biodb/polypeptides/Q9GZZ6) Details (/biodb/polypeptides/Q9GZZ6)

Kind Protein
Organism Human
Pharmacological action yes
Actions antagonist

General Function: Receptor binding


Specific Function: Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits
and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of
which may activate a potassium current which hyperpolarizes t...
Gene Name: CHRNA10
Uniprot ID: Q9GZZ6 (http://www.uniprot.org/uniprot/Q9GZZ6)

8 dari 13 12/6/2016 9:06 PM


Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

Molecular Weight: 49704.295 Da

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 (http://www.ncbi.nlm.nih.gov/pubmed/17139284)]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 (http://www.ncbi.nlm.nih.gov/pubmed/17016423)]

4. Delta-type opioid receptor (/biodb/polypeptides/P41143) Details (/biodb/polypeptides/P41143)

Kind Protein
Organism Human
Pharmacological action yes
Actions agonist

General Function: Opioid receptor activity


Specific Function: G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that
triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads
to the inhibition of adenylate cyclase activity. Inhibits neurot...
Gene Name: OPRD1
Uniprot ID: P41143 (http://www.uniprot.org/uniprot/P41143)
Molecular Weight: 40368.235 Da

References

1. Gross ER, Hsu AK, Gross GJ: Acute methadone treatment reduces myocardial infarct size via the delta-opioid receptor in rats during reperfusion. Anesth Analg. 2009 Nov;109(5):1395-402. doi:
10.1213/ANE.0b013e3181b92201. [PubMed:19843777 (http://www.ncbi.nlm.nih.gov/pubmed/19843777)]

5. 5-hydroxytryptamine receptor 3A (/biodb/polypeptides/P46098) Details (/biodb/polypeptides/P46098)

Kind Protein
Organism Human
Pharmacological action unknown
Actions antagonist

General Function: Voltage-gated potassium channel activity


Specific Function: This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen.
This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively
nonselective, ion channel.
Gene Name: HTR3A
Uniprot ID: P46098 (http://www.uniprot.org/uniprot/P46098)
Molecular Weight: 55279.835 Da

References

1. Deeb TZ, Sharp D, Hales TG: Direct subunit-dependent multimodal 5-hydroxytryptamine3 receptor antagonism by methadone. Mol Pharmacol. 2009 Apr;75(4):908-17. doi: 10.1124/ mol.108.053322. Epub 2009 Jan
8. [PubMed:19131665 (http://www.ncbi.nlm.nih.gov/pubmed/19131665)]

Enzymes

1. Cytochrome P450 3A4 (/biodb/polypeptides/P08684) Details (/biodb/polypeptides/P08684)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor inducer

General Function: Vitamin d3 25-hydroxylase activity


Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally
unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name: CYP3A4
Uniprot ID: P08684 (http://www.uniprot.org/uniprot/P08684)
Molecular Weight: 57342.67 Da

References

1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem.
2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 (http://www.ncbi.nlm.nih.gov/pubmed/19515014)]
2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]
3. Kharasch ED, Hoffer C, Whittington D, Sheffels P: Role of hepatic and intestinal cytochrome P450 3A and 2B6 in the metabolism, disposition, and miotic effects of methadon e. Clin Pharmacol Ther. 2004
Sep;76(3):250-69. [PubMed:15371986 (http://www.ncbi.nlm.nih.gov/pubmed/15371986)]
4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

2. Cytochrome P450 2C19 (/biodb/polypeptides/P33261) Details (/biodb/polypeptides/P33261)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Steroid hydroxylase activity


Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates,
diazepam, propranolol, citalopram and imipramine.
Gene Name: CYP2C19
Uniprot ID: P33261 (http://www.uniprot.org/uniprot/P33261)
Molecular Weight: 55930.545 Da

References

9 dari 13 12/6/2016 9:06 PM


Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem.
2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 (http://www.ncbi.nlm.nih.gov/pubmed/19515014)]
2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]

3. Cytochrome P450 3A5 (/biodb/polypeptides/P20815) Details (/biodb/polypeptides/P20815)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Oxygen binding


Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name: CYP3A5
Uniprot ID: P20815 (http://www.uniprot.org/uniprot/P20815)
Molecular Weight: 57108.065 Da

References

1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

4. Cytochrome P450 3A7 (/biodb/polypeptides/P24462) Details (/biodb/polypeptides/P24462)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Oxygen binding


Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name: CYP3A7
Uniprot ID: P24462 (http://www.uniprot.org/uniprot/P24462)
Molecular Weight: 57525.03 Da

References

1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

5. Cytochrome P450 2D6 (/biodb/polypeptides/P10635) Details (/biodb/polypeptides/P10635)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor

General Function: Steroid hydroxylase activity


Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics,
adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name: CYP2D6
Uniprot ID: P10635 (http://www.uniprot.org/uniprot/P10635)
Molecular Weight: 55768.94 Da

References

1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem.
2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 (http://www.ncbi.nlm.nih.gov/pubmed/19515014)]
2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]
3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

6. Cytochrome P450 2B6 (/biodb/polypeptides/P20813) Details (/biodb/polypeptides/P20813)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Steroid hydroxylase activity


Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name: CYP2B6
Uniprot ID: P20813 (http://www.uniprot.org/uniprot/P20813)
Molecular Weight: 56277.81 Da

References

1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem.
2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 (http://www.ncbi.nlm.nih.gov/pubmed/19515014)]
2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]
3. Kharasch ED, Hoffer C, Whittington D, Sheffels P: Role of hepatic and intestinal cytochrome P450 3A and 2B6 in the metabolism, disposition, and miotic effects of methadon e. Clin Pharmacol Ther. 2004
Sep;76(3):250-69. [PubMed:15371986 (http://www.ncbi.nlm.nih.gov/pubmed/15371986)]
4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

10 dari 13 12/6/2016 9:06 PM


Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

7. Cytochrome P450 2C8 (/biodb/polypeptides/P10632) Details (/biodb/polypeptides/P10632)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Steroid hydroxylase activity


Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15-
and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name: CYP2C8
Uniprot ID: P10632 (http://www.uniprot.org/uniprot/P10632)
Molecular Weight: 55824.275 Da

References

1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem.
2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 (http://www.ncbi.nlm.nih.gov/pubmed/19515014)]
2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]

8. Aromatase (/biodb/polypeptides/P11511) Details (/biodb/polypeptides/P11511)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Oxygen binding


Specific Function: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name: CYP19A1
Uniprot ID: P11511 (http://www.uniprot.org/uniprot/P11511)
Molecular Weight: 57882.48 Da

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]

9. Cytochrome P450 1A2 (/biodb/polypeptides/P05177) Details (/biodb/polypeptides/P05177)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of
one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized
primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name: CYP1A2
Uniprot ID: P05177 (http://www.uniprot.org/uniprot/P05177)
Molecular Weight: 58293.76 Da

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]

10. Cytochrome P450 2C18 (/biodb/polypeptides/P33260) Details (/biodb/polypeptides/P33260)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Steroid hydroxylase activity


Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name: CYP2C18
Uniprot ID: P33260 (http://www.uniprot.org/uniprot/P33260)
Molecular Weight: 55710.075 Da

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]

11. Cytochrome P450 2C9 (/biodb/polypeptides/P11712) Details (/biodb/polypeptides/P11712)

Kind Protein
Organism Human
Pharmacological action unknown
Actions substrate

General Function: Steroid hydroxylase activity


Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It

11 dari 13 12/6/2016 9:06 PM


Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability
of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
G e n e N a m e : CYP2C9
U n ip r o t ID : P11712 (http://www.uniprot.org/uniprot/P11712)
M o le c u la r W e ig h t : 55627.365 Da

R e f e r e n c e s

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for
analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]

Transporters

1 . M u lt id r u g r e s is t a n c e p r o t e in 1 ( / b io d b / p o ly p e p t id e s / P 0 8 1 8 3 ) Details (/biodb/polypeptides/P08183)

K in d Protein
O r g a n is m Human
P h a r m a c o lo g ic a l a c t io n unknown
A c t io n s inhibitor

G e n e r a l F u n c t io n : Xenobiotic-transporting atpase activity


S p e c if ic F u n c t io n : Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
G e n e N a m e : ABCB1
U n ip r o t ID : P08183 (http://www.uniprot.org/uniprot/P08183)
M o le c u la r W e ig h t : 141477.255 Da

R e f e r e n c e s

1. Stormer E, Perloff MD, von Moltke LL, Greenblatt DJ: Methadone inhibits rhodamine123 transport in Caco-2 cells. Drug Metab Dispos. 2001 Jul;29(7):954-6.
[PubMed:11408360 (http://www.ncbi.nlm.nih.gov/pubmed/11408360)]
2. Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein
(ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017 (http://www.ncbi.nlm.nih.gov/pubmed/19887017)]

C o m m e n t s

3 Comments DrugBank 1 Login

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Join the discussion

Pamato9 5 years ago


Can you add whether this is a control drug or not and what schedule it (e.g. II or III or IV V) can you do this for all drugs?
5 Reply Share

Vivian Law Mod 5 years ago


Methadone is listed as a Schedule II drug under the Controlled Substances Act in the United States. In Canada, methadone falls under the Narcotic Control Regulations under the
Controlled Drugs and Substances Act. We may consider adding schedule information for certain countries in the future.
1 Reply Share

Brenton Horne 4 years ago


In Australia it is a Schedule 8 (controlled) drug.
Reply Share

DRUGBANK

AN2690 (DB05058) Butriptyline (DB09016)



Dear,By the way this is not the same as Tavaborole (DB09041)? Hi Jerod Poore,Thank you for pointing this out. We will review the
available literature and update the description.Adam

Belatacept (DB06681) Eribulin (DB08871)



Can someone simply explainthe amino acid sequence difference Thanks for the fix :)
between abatacept and belatacept? Do theyonly differ by two amino acids? If so, are they
both structurally identical? Inother words, will the secondary, tertiary and quaternary

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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23

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12 dari 13 12/6/2016 9:06 PM


Methadone - DrugBank https://www.drugbank.ca/drugs/DB00333

T h is p r o je c t is s u p p o r te d b y th e C a n a d ia n In s t it u te s o f H e a lt h R e s e a r c h ( h ttp ://w w w .c ih r - ir s c .g c .c a ) ( a w a r d # 1 1 1 0 6 2 ) ,

A lb e r ta In n o v a te s - H e a lt h S o lu t io n s ( h ttp ://w w w .a ih e a lt h s o lu t io n s .c a ) , a n d b y T h e M e ta b o lo m ic s In n o v a t io n C e n tr e (http://www.metabolomicscentre.ca)


( T M IC ) ( h ttp :/ / w w w .m e ta b o lo m ic s c e n tr e .c a /) , a n a t io n a lly - f u n d e d r e s e a r c h a n d c o r e fa c ilit y th a t s u p p o r ts a w id e

r a n g e o f c u t t in g - e d g e m e ta b o lo m ic s tu d ie s . T M IC is fu n d e d b y G e n o m e A lb e r ta ( h ttp :/ / w w w .g e n o m e a lb e r ta .c a ) ,

G e n o m e B r it i s h C o lu m b ia ( h ttp ://w w w .g e n o m e b c .c a /) , a n d G e n o m e C a n a d a ( h ttp ://w w w .g e n o m e c a n a d a .c a ) , a


(http://www.cihr-irsc.gc.ca) (http://www.aihealthsolutions.ca) (http://genomealberta.ca
n o t- fo r - p r o f it o r g a n iz a t io n th a t is le a d in g C a n a d a 's n a t io n a l g e n o m ic s s tr a te g y w it h $ 9 0 0 m i ll i o n in fu n d in g fr o m th e

fe d e r a l g o v e r n m e n t. M a in te n a n c e , s u p p o r t, a n d c o m m e r c ia l lic e n s in g is p r o v id e d b y O M x P e r s o n a l H e a lt h A n a ly t ic s ,

In c . ( h ttp :/ / o m x . io )

13 dari 13 12/6/2016 9:06 PM

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