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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

Molecular Formula C22H43N5O12
Molecular Weight 569.6031
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Isepamicin

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
G7K224460P
Record Status Validated (UNII)
Record Version