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OH
HO
H2N
OH
2
3
HO
HO
OH
OH
Cyclitol
(polyalcol vng)
Genin: L cc diaminocyclitol
1. Dn cht 1,3-diaminocyclitol:
Gm 3 cu trc: streptidin,
streptamin.
H2N
OH
C HN
HO
NH
2
3
NH C
H2N
NH2
streptamin
H2N
deoxy-2
2
3
NH2
OH
HO
OH
OH
Streptidin
Streptamin
OH
NH2
HO
OH
Aminocyclitol
6
5
OH
OH
NH
NH2
6
5
OH
OH
Deoxy-2 streptamin
(dideoxy-1,3
diamino-1,3
cyclitol)
H2N
2
3
Ose O
NH2
H2N
O Ose
2
3
Ose O
NH2
OH
O Ose
5
OH
Dn cht th 4,6
Dn cht th 4,5
c tnh:
Th 4,5
th 4,6
(khng c tim)
(tim c)
2. Dn cht 1,4-diaminocyclytol (fortamin): Cht in hnh
l fortimicin.
CH NH
Me
NH2
O
NH2
OH
OMe
6
4
HO
. 2 H2SO4
Me
CO CH2NH2
Fortimicin A sulfat
HO
HO
NH2
OH
H2N
H3C
NH2
HO
NH2
CH
O
OH
NH2
Garosamin
Sisosamin
+ ng 5 cnh:
H3C
OH
OH
D-glucosamin-3
O
OH
OH
H2N
CH2 NH2
HO
OH
D-glucosamin-2
Neosamin C
HO
CH2OH
HO
CH2 NH2
O
OH
NH2
Purpurosamin
HOH2C
OH
OH
CHO
L
streptose
ribose
OH OH
OH OH
AMINOSID
Streptamin Streptidin
Deoxy-2 streptamin
Genin
Th 4,5
Th 4,6
OH
Aminosid
Kanamycin
Spectinomycin
thin
Neomycin
Streptomycin
Paromomycin
Gentamicin
nhin
Lividomycin
Tobramycin
Ribostamycin
Sisomicin
Aminosid
Dihydrostreptomycin
Amikacin
BTH
Dibecacin
Netilmicin
Bng 3-Aminosid/dh
* Ngun gc:
T mi trng
Streptomyces (S.)
nui
cy
Micromonospora
(M.);
Cng thc:
CH2OH
O
HO
1
,,
NH
H3C
L streptose
CHO
2
OH
,,
OH NHCH3
H2N C HN
NH
NH C NH2
2
1
L glucosamin
OH
OH
OH
. 3 H2SO4
Streptidin
2
Tnh cht:
Bt mu trng, v ng, ht m mnh;
D tan trong nc; kh tan trong cc dung mi hu c.
Dung dch nc khng bn (nhanh b kt ta dng base).
Ha tnh-nh tnh:
- un si streptomycin/NaOH: gii phng NH3 (guanin).
- un si vi thuc th Fehling: Cu2O mu nu (tnh
kh).
- un si streptomycin/NaOH cho maltol, to mu tm vi
FeCl3:
H3C
O
CHO
,
OH OR
OR
H3C
OH , t
H3C
+
HO
Maltol O
Fe
3+
Fe 3
O
O
Phc vi st (III)-tm
Bng 5-aminosid/dh
Dn cht th 4,6 ca deoxy-2 streptamin:
Gm: Gentamicin, kanamycin, tobramycin, sisomicin v netilmicin
(BTH).
Gentamicin
Ngun gc: T mi trng nui cy Micromonospora purpurea v M.
khc.
Hn hp cc gentamicin A, B, C1, C1a, C2, C2a, X.
R3
CH R4
O
,
1
R2 ,
H2N
2
1
4
NH2
R1
OH
,,
H3CHN
2
,,
R6
OH
OH
H2N
2
1
4
NH2
NH C2H5
O
OH
OH
,,
H3CHN
2
CH3
,,
. 5 H2SO4
2
OH
- Neomycin B
R1 = H; R2= -CH2NH2
- Neomycin C
HO
Neosamin
R2
HO
OH ,
2
6
5
NH2
O
O
OH
O
HOH2C
OH D ribose
R1
OH
,, O
5
O
OH
,,
,,
NH2
R1 = -CH2NH2; R2= H
Bng 7-Aminosid/dh
Neomycin-tip
Tnh cht:
Bt mu trng ng, v ng.
D tan trong nc; tan nh trong ethanol; khng tan trong d/m
hu c.
nh tnh:
- Cho mu tm vi ninhydrin.
- Sc k: Sc cho 3 vt tng ng neomycin sulfat
chun.
nh lng:
- Phng php vi sinh: Hot lc 680 UI/1 mg cht th.
- Hm lng SO42-: 27-31%.
Ph tc dng:
+ Trn hu ht VK gram(-), k c Vibrio cholerae (t).
+ Khng tc dng trn TK m xanh.
+ Nhy cm vi khun gram (+), tr hu ht lin cu.
Ch nh:
- Dng ngoi: Thuc m 3-5 mg/g thuc.
Phi hp vi khng sinh polypeptit, nystatin iu tr a
nhim da.
- Ung lm sch rut trc phu thut bng.
c tnh: Chung ca aminosid; c tnh cao khng c tim.
Bo qun: ch mt.
Framycetin: Ch phm thun neomycin B, ngun gc t
Streptomyces decaris.
Ch nh, cch dng: Tng t neomycin.
Aminosid dn cht Streptamin
Spectinomycin hydroclorid
Ngun gc: T mi trng nui cy Streptomyces spectabilis
Cng thc:
OH
Tnh cht:
H3C HN
HO
O
NHCH3
OH
CH3
. 2HCl . 5H2O
NH2
H2N
HO
NH2
OH
D Glucosamin
C18H37N5O9
ptl : 467,5
Tnh cht: Bt kt tinh mu trng. Rt d tan trong nc; kh tan
trong alcol.
nh tnh:
- Dung dch 5 mg tobramycin trong nc, thm ninhydrin 0,1%;
un cch thu: xut hin mu xanh tm.
- Sc k lp mng, so vi tobramycin chun.
nh lng: Bng cc phng php:
- Phng php vi sinh. Hot lc khng thp hn 930 UI/mg.
- HPLC, so vi tobramycin chun.
Ph tc dng:
Tc dng trn hu ht cc vi khun gram (-); trn vi khun gram
(+) rt nhy cm vi t cu vng; vi trc khun m xanh hiu lc cao
hn gentamicin. Khng tc dng trn nhiu chng lin cu.
H2N
CH2NH2
HO
O
OH
1"
2"
OH
2
5
NH R
O
OH
1''
CH2OH
2"
OH
OH
Streptomyces
Kanamycin
R=H
Amikacin
OH
NH2
R=
CO C CH2CH2 NH2
H
H3C
CH
NH2
O
OH
6
O
NH2
HO
. 2H2SO4
OCH3
CH3
CO CH2 NH2
C17H35N5O6 . 2H2SO4
ptl : 601,70
Tnh cht:
Bt v nh hnh mu trng, b bin mu trong khng kh, nh
sng; nng chy khong 200o C. Tan trong nc; tan nh trong ethanol;
hu nh khng tan trong nhiu dung mi hu c. []D20 khong +87o.
Ph tc dng: Tng t gentamicin; nhy cm t cu vng khng
methicilin.
Ch nh: Tng t gentamicin sulfat.
Liu dng: Tim bp hoc truyn 200 mg/ln 2 ln/24 h.
Bo qun: Trnh m.
Bng 10-Tetra./dh
Octahydronaphtacen
* Cu trc chung:
R1
8
9
R6
R3
6
R2 R4
5
10
11
12
OH
OH
H
4a
12 a
OH
N (CH3)2
OH
3
2
CO R5
R1
Clotetracyclin( -Cl
R2
R3
R4
R5
R6
-CH3 -OH
-H
-NH2
-H
Pht
hin
1948
-CH3 -OH
-OH
-NH2
-H
1950
-CH3 -OH
-H
-OH
-H
-H
-NH2
-NH2
-H
-H
1953
1957
-H
-OH
-CH3 -H
=CH2
-H
-H
-H
-H
-H
-H
-CH3 -OH
-CH3 -OH
-CH3 -OH
-CH3 -OH
-H
-OH
-OH
-H
-H
-H
-OH
-H
-H
-H
-NH2
-NH2
-NH2
-NH2
-NH2
-NH2
-CH3
-NHX
-NHZ
-NHY
-H
-H
-H
-H
-H
-NH2
-H
-H
-H
-H
1957
1958
1960
1964
1960
*)
Oxytetracyclin -H
(*)
Tetracyclin(*)
-H
Demeclocyclin -Cl
(*)
Demecyclin(*)
Doxycyclin
Methacyclin
Minocyclin
Sancyclin
Amicyclin
Terramycin X(*)
Lymecyclin
Mepicyclin
Rolicyclin
-H
-H
-H
-N(Me)2
-H
-H
-H
-H
-H
-H
1960
1962
1959
1958
Chng S.
cho KS
Ngun
gc
Th
h
T1/2
(h)
S.
aureofacien
s
Oxytetracycl S. rimosus
TN
5-6
TN
S.
viridifaciens
Demeclocycl S.
in
aureofacien
s
Demecyclin S.
aureofacien
s
TN
6-9
TN
II
10-17
TN
Doxycyclin
Metacyclin
Minocyclin
Limecyclin
Mepicyclin
Rolitetracycl
in
+
+
+
+
+
+
II
II
II
I
I
I
Clotetracycli
n
in
Tetracyclin
Bn/
H+
15-20
12-20
4-6
4-6
4-6
Tan/H2O
+
+
+
Ghi ch:
- Cc cht c tn chng Streptomyces l KS thin nhin.
- Cc tin tetracyclin: Limecyclin, Mepicyclin, Rolitetracyclin.
Tnh cht dc ng hc, tai bin:
+ Hp thu ng tiu ha:
- Mi cht c mc khc nhau.
- Demecyclin: KS thin nhin; km hp thu khi ung.
+ Thi tr: T l cao qua ng mt-rut; mt phn qua ng
thn-nc tiu.
+ Tai bin:
- i lc cao vi ion Ca++, tp trung xng, rng gy xn
mu, gin xng d gy; nh hng xu ti pht trin xng, rng
(tr em < 7 tui).
- Sn phm chuyn ha anhydrotetracyclin) kch ng, hoi t
ng thn.
- Tc dng trn vi khun rut (gram -): gy ri lon tiu ha.
- Mn cm thuc: Khng xy ra thng xuyn.
Ch nh:
N (CH3)2
OH
H+
A
1
OH
A
1
CONH2
OH
N (CH3)2
OH
CONH2
Cng thc:
Tetracyclin H
hydroclorid
N (CH )
CH3
HO
OH
3 2
OH
OH
OH
CONH2
O
. HCl
H3C
OH
N (CH3)2
OH
. HCl .
OH
OH
OH
1
2
H2O .
1
2
C2H5OH
CONH2
O
OH
OH
OH
N (CH3)2
OH
CONH2
O