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
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
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10749517
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10749517 |
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Target ID: CHEMBL614427 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10749517 |
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Target ID: CHEMBL612951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17353252 |
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Target ID: CHEMBL612641 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17353252 |
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Target ID: map03010 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Isepamicin Approved UseFor the treatment of susceptible infections. |
PubMed
Title | Date | PubMed |
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Comparative nephrotoxicity of SCH 21420 and amikacin in rats. | 1979 Oct |
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Auditory impairment in guinea pigs treated with isepamicin. | 1995 Jun |
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Effects of some antibiotics on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro and in vivo study. | 2004 Aug |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10749517
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.
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NCI_THESAURUS |
C2363
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QJ01GB11
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J01GB11
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m6421
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C83838
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ISEPAMICIN
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)