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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H43N5O12.H2O4S
Molecular Weight 667.682
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISEPAMICIN SULFATE

SMILES

OS(O)(=O)=O.[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=DDXRHRXGIWOVDQ-MGAUJLSLSA-N
InChI=1S/C22H43N5O12.H2O4S/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;1-5(2,3)4/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34);(H2,1,2,3,4)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C22H43N5O12
Molecular Weight 569.6031
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:35:11 GMT 2023
Edited
by admin
on Sat Dec 16 08:35:11 GMT 2023
Record UNII
F2L211KBUV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISEPAMICIN SULFATE
JAN   MI   WHO-DD  
Common Name English
Isepamicin sulfate [WHO-DD]
Common Name English
EXACIN
Brand 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))-N1-((2S)-3-AMINO-2-HYDROXY-1-OXOPROPYL)-2-DEOXY-, SULFATE (1:1) (SALT)
Systematic Name English
ISEPAMICIN SULFATE [JAN]
Common Name English
ISPALLIN
Brand Name English
ISEPAMICIN SULFATE [MI]
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))-N1-((3S)-3-AMINO-2-HYDROXY-1-OXOPROPYL)-2-DEOXY-, SULFATE (SALT)
Systematic Name English
ISEPACIN
Brand Name English
ISEPAMICIN MONOSULFATE
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL272080
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
PRIMARY
CAS
67814-76-0
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
NON-SPECIFIC STOICHIOMETRY
EVMPD
SUB02782MIG
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
PRIMARY
MERCK INDEX
m6421
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
PRIMARY Merck Index
SMS_ID
100000088388
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
PRIMARY
FDA UNII
F2L211KBUV
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
PRIMARY
CAS
393574-17-9
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
PRIMARY
PUBCHEM
636375
Created by admin on Sat Dec 16 08:35:11 GMT 2023 , Edited by admin on Sat Dec 16 08:35:11 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY