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Isepamicin

Names

[ CAS No. ]:
58152-03-7

[ Name ]:
Isepamicin

[Synonym ]:
UNII-G7K224460P
(2S)-3-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-2-{[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy}-3-hydroxycyclohexyl]-2-hydroxypropanamide
isepamicin
изепамицин
HAPA-B
ISEPAMICIN SULPHATE
propanamide, 3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-2-[[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2S)-
Propanamide, 3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-2-[[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2 S)-
Isepamycin
hapa-gentamycinb

Biological Activity

[Description]:

Isepamicin (Sch 21420) is an aminoglycoside antibacterial. Isepamicin has better activity against strains producing type I 6'-acetyltransferase. Isepamicin’s antibacterial spectrum includes Enterobacteriaceae and staphylococci. Anaerobes, Neisseriaceae and streptococci are resistant. Isepamicin exhibits a strong concentration-dependent bactericidal effect, a long post-antibiotic effect (several hours) and induces adaptive resistance[1].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Tod M, et al. Clinical pharmacokinetics and pharmacodynamics of isepamicin. Clin Pharmacokinet. 2000;38(3):205-223.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
926.8±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C22H43N5O12

[ Molecular Weight ]:
569.603

[ Flash Point ]:
514.3±34.3 °C

[ Exact Mass ]:
569.290833

[ PSA ]:
297.72000

[ LogP ]:
-2.45

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.641

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WK1972000
CHEMICAL NAME :
D-Streptamine, O-6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(3-d eoxy-4-C-methyl-3- (methylamino)-beta-L-arabinopyranosyl-(1-6))-N(sup 1)-(3-amino-2-hydroxy-1-oxopropyl)- 2-deoxy-, (S)-
CAS REGISTRY NUMBER :
58152-03-7
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C22-H43-N5-O12
MOLECULAR WEIGHT :
569.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
330 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 29,543,1986 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3150 mg/kg/21D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - changes in bladder weight
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 33(Suppl 5),47,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
5600 mg/kg/4W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Ear) - changes in vestibular functions Sense Organs and Special Senses (Ear) - changes in cochlear structure or function Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 33(Suppl 5),90,1985

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds