(S)-O-6-Amino-6-desoxy-α-D-glucopyranosyl-(1-4)-O-[3-desoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1-6)]-1,3-diamino-N1-(3-aminolactoyl)-1,2,3-tridesoxy-D-scyllo-inosit

Isepamicin

HCID 3037209CAS 58152-03-7
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

Standard-SMILES
CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](N)C[C@H]2NC(=O)[C@@H](O)CN)OC[C@]1(C)O
InChIKey
UDIIBEDMEYAVNG-ZKFPOVNWSA-N
Summenformel
C22H43N5O12
Durchschnittliche Molmasse
569,6 g/mol
Monoisotopische Masse
569,29082182

Überblick

Isepamicin is a broad-spectrum aminoglycoside antibiotic structurally related to gentamicin and amikacin. Isepamicin has activity similar to amikacin but with better activity against bacterial strains with resistance to other aminoglycosides, such as strains producing 6'-N-aminoglycoside acetyltransferase. Isepamicin is not metabolized and is excreted via the kidneys. This agent exerts a long postantibiotic effect allowing for once daily dosing.

Namen und Bezeichner

Bevorzugter Name
Isepamicin
IUPAC
(2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxypropanamide
Lokaler Name
(S)-O-6-Amino-6-desoxy-α-D-glucopyranosyl-(1-4)-O-[3-desoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1-6)]-1,3-diamino-N1-(3-aminolactoyl)-1,2,3-tridesoxy-D-scyllo-inosit
Englischer Name
Isepamicine
Summenformel
C22H43N5O12
Molmasse
569.6

Namen und Synonyme

IsepamicinIsepamicine58152-03-7HAPA-BIsepamicinaSch 21420HAPA-gentamycin BIsepamicinumSch-21420G7K224460PDTXSID1048380(2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxypropanamide
Weitere Namen anzeigen
ISEPAMICIN SULPHATEsch21420Isemapicinhapa-gentamycinbIsepamicine USP/EP/BP(s)-y-1-oxopropyl)-2-deoxyIsepamicin Sulfate Impurity Ⅲ:Isepamicine
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)-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-(3-amino-2-hydroxy-1-oxopropyl)-2-deoxy-, (S)-(2S)-3-amino-N-((1R,2S,3S,4R,5S)-5-amino-4-((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl)oxy-2-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl)oxy-3-hydroxycyclohexyl)-2-hydroxypropanamideRefChem:7915071-N-HAPA-gentamicin BCHEBI:37951J01GB11DTXCID601508530

Datenbank-Bezeichner

CAS
58152-03-7
PubChem CID
3037209
DTXSID
DTXSID1048380
ChEMBL
CHEMBL272080
UNII
G7K224460P
EC Number
261-143-4
Nikkaji
J22.232A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-6,9
Polarare Oberfläche (TPSA)
298 Ų
H-Brücken-Donoren
12
H-Brücken-Akzeptoren
16
Frei drehbare Bindungen
9
Schwere Atome
39

Physikochemische Eigenschaften

Siedepunkt
633.08 °C · 633.08°C (rough estimate)
Dichte
1.3531 · 1.3531 (rough estimate)
Brechungsindex
1.75 · 1.7500 (estimate)
pka
11.01 · 11.01±0.35(Predicted)

Sicherheit und Regulatorisches

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Isepamicin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Anwendungen · 2 Einträge

BeschreibungIsepamicin is a aminoglycoside antibiotic indicated for use in the treatment of urinary and respiratory tract infections. Although it is less potent than most other aminoglycosides, it is also less nephrotoxic. The broad-spectrum activity of isepamicin generally parallels that of amikacin in vitro.

VerwendenAntibacterial (aminoglyco side).

Vor- und nachgelagerte Produkte

Anbieter26 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
重庆乾泰医药研究院有限公司17864179792 · [email protected]
湖北扬信医药科技有限公司0714-3999001 19171453112 · [email protected]

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