U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H43N5O12
Molecular Weight 569.6031
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISEPAMICIN

SMILES

[H][C@]3(O[C@H]1[C@@H](C[C@H](N)[C@@H](O[C@@]2([H])O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O)NC(=O)[C@@H](O)CN)OC[C@](C)(O)[C@H](NC)[C@H]3O

InChI

InChIKey=UDIIBEDMEYAVNG-ZKFPOVNWSA-N
InChI=1S/C22H43N5O12/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10749517

Isepamicin is an aminoglycoside antibacterial with properties similar to those of amikacin, but with better activity against strains producing type I 6'-acetyltransferase. The antibacterial spectrum includes Enterobacteriaceae and staphylococci. Anaerobes, Neisseriaceae and streptococci are resistant. The lower and upper break-points are 8 and 16 mg/L. Like other aminoglycosides, isepamicin exhibits a strong concentration-dependent bactericidal effect, a long post-antibiotic effect (several hours) and induces adaptive resistance. Isepamicin is administered intravenously or intramuscularly at a dosage of 15 mg/kg once daily or 7.5 mg/kg twice daily. Isepamicin is not bound to plasma proteins, and it distributes in extracellular fluids and into some cells (outer hair cells, kidney cortex) by active transport. Isepamicin has been developed and approved for clinical use in the 1990s.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Isepamicin

Approved Use

For the treatment of susceptible infections.
PubMed

PubMed

TitleDatePubMed
Comparative nephrotoxicity of SCH 21420 and amikacin in rats.
1979 Oct
Auditory impairment in guinea pigs treated with isepamicin.
1995 Jun
Effects of some antibiotics on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro and in vivo study.
2004 Aug
Deficiency of polycystin-2 reduces Ca2+ channel activity and cell proliferation in ADPKD lymphoblastoid cells.
2004 May
Patents

Sample Use Guides

Parenteral Susceptible infections Adult: Up to 15 mg/kg daily by IM injection or IV infusion in 2 divided doses. Adjust dose based on serum isepamicin conc monitoring. Total dose should not exceed 1.5 g/day. Max Dosage: 1.5 g daily.
Route of Administration: Parenteral
The 90% minimum inhibitory concentration (MIC90) ranged from 1.1 to 8.5 mg/L for members of the Enterobacteriaceae. Pseudomonas aeruginosa and Acinetobacter spp. have MIC90 values of 7.8 and 7.2 mg/L, respectively.
Name Type Language
ISEPAMICIN
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
ISEPAMICIN [MI]
Common Name English
1-N-((S)-3-AMINO-2-HYDROXYPROPIONYL)GENTAMICIN B
Common Name English
isepamicin [INN]
Common Name English
Isepamicin [WHO-DD]
Common Name English
D-STREPTAMINE, O-6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6))-N(SUP 1)-(3-AMINO-2-HYDROXY-1-OXOPROPYL)-2-DEOXY-, (S)-
Common Name English
O-6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6))-2-DEOXY-N(SUP 1)-((S)-ISOSERYL)-D-STREPTAMINE
Common Name English
SCH-21420
Code English
HAPA-B
Common Name English
SCH 21420
Code English
ISEPAMICIN [JAN]
Common Name English
ISEPAMICIN [USAN]
Common Name English
ISEPAMICIN [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2363
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
WHO-VATC QJ01GB11
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
WHO-ATC J01GB11
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
Code System Code Type Description
INN
5849
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
MERCK INDEX
m6421
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY Merck Index
EVMPD
SUB08309MIG
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PRIMARY
ChEMBL
CHEMBL272080
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PRIMARY
NCI_THESAURUS
C83838
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
ECHA (EC/EINECS)
261-143-4
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PRIMARY
CAS
58152-03-7
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PRIMARY
EPA CompTox
DTXSID1048380
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
DRUG BANK
DB13540
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
SMS_ID
100000083381
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
FDA UNII
G7K224460P
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
WIKIPEDIA
ISEPAMICIN
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
PUBCHEM
3037209
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
USAN
W-11
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY
DRUG CENTRAL
1486
Created by admin on Fri Dec 15 15:39:43 GMT 2023 , Edited by admin on Fri Dec 15 15:39:43 GMT 2023
PRIMARY