Isepamicin

Chemical compound

J01GB11 (WHO)

Identifiers

IUPAC name

(2S)-3-amino-N-((1R,2S,3S,4R,5S)-5-amino-4-[(6-amino-6-deoxy-D-glucopyranosyl)oxy]-2-{[3-deoxy-4-C-methyl-3-(methylamino)-L-arabinopyranosyl]oxy}-3-hydroxycyclohexyl)-2-hydroxypropanamide

CAS Number

58152-03-7^Y

PubChem CID

3037209

ChemSpider

2301019^N

UNII

G7K224460P

ChEMBL

ChEMBL272080^N

CompTox Dashboard (EPA)

DTXSID1048380

ECHA InfoCard100.055.567

Chemical and physical dataFormulaC₂₂H₄₃N₅O₁₂Molar mass569.609 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N)NC(=O)[C@H](CN)O)O

InChI

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^N
Key:UDIIBEDMEYAVNG-ZKFPOVNWSA-N^N

^NY (what is this?) (verify)

Isepamicin (also Isepamycin) is an aminoglycoside antibiotic.

It was patented in 1973 and approved for medical use in 1988.^[1] It has been identified by the World Health Organization as a Critically Important Antimicrobial for human use.^[2]

References

^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 508. ISBN 9783527607495.
^ "Critically important antimicrobials for human medicine" (PDF). World Health Organization. 2012.

Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Boromycin Carbomycin Carrimycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Gamithromycin Josamycin Kitasamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Solithromycin Spiramycin Telithromycin Tildipirosin Tilmicosin Troleandomycin Tulathromycin Tylosin Tylvalosin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)