Cefpirome

HCID 5479539CAS 84957-29-9
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Grundinformationen

Standard-SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3cccc4c3CCC4)CS[C@H]12)c1csc(N)n1
InChIKey
DKOQGJHPHLTOJR-WHRDSVKCSA-N
Summenformel
C22H22N6O5S2
Durchschnittliche Molmasse
514,6 g/mol
Monoisotopische Masse
514,1093098

Überblick

Cefpirome is a fourth-generation cephalosporin antibiotic having 6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively. It is a cephalosporin and a cyclopentapyridine.

Namen und Bezeichner

Bevorzugter Name
Cefpirome
IUPAC
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Englischer Name
Cefpirome
Summenformel
C22H22N6O5S2
Molmasse
514.58

Namen und Synonyme

CEFPIROME84957-29-9CefpiromaCefpiromumCefirHR 810HR-810 FREE BASES72Q2F09HY(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHR-810CHEBI:3503DTXSID2048244
Weitere Namen anzeigen
CEFPIROME SULPHATEKeitimCS-283CerfpiromeCefpirome-13C-D3Cefpiromum [latin]
810, HR5H-1-Pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-5H-1-Pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-(6R,7R)-7-(((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl)amino)-3-(6,7-dihydro-5H-cyclopenta(b)pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate1-(((6R,7R)-2-carboxylato-7-(((2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5H,6H,7H-cyclopenta(b)pyridin-1-ium1-{[(6R,7R)-2-carboxylato-7-{[(2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium3-((2,3-cyclopenteno-1-pyridinium)methyl)-7-(2-syn-methoximino-2-(2-aminothiazole-4-yl)acetamido)ceph-3-em-4-carboxylateRefChem:124246

Datenbank-Bezeichner

CAS
84957-29-9
PubChem CID
5479539
DTXSID
DTXSID2048244
ChEMBL
CHEMBL65794
ChEBI
CHEBI:3503
UNII
S72Q2F09HY
Nikkaji
J32.848K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,9
Polarare Oberfläche (TPSA)
207 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
10
Frei drehbare Bindungen
6
Schwere Atome
35

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Antibiotics

Physikochemische Eigenschaften

storage temp.
2 · 2-8°C(protect from light)

Sicherheit und Regulatorisches

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Cefpirome

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Sicherheitsdaten

risk_code
36/37/38-42/43
Toxizität
LD50 in mice, rats (g/kg): 1.9-2.4, 1.9-2.15 i.v.; 3.8-4.2, 5.8-6.55 i.p. (Donaubauer, Mayer)
hazard_code
Xi
safety_code
22-26-36/37/39

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Mechanism of ActionCefpirome is a β-lactam (cephalosporin) antibiotic that binds penicillin-binding proteins (PBPs) and inhibits peptidoglycan cross-linking in bacterial cell-wall synthesis.
MeSH Pharmacological ClassificationBactericidal agents that contain a beta-lactam ring in their chemical structure. They inhibit bacterial cell wall synthesis by binding to PENICILLIN-BINDING PROTEINS, preventing the synthesis of peptidoglycan in bacterial cell walls.
Anwendungen · 2 Einträge

BeschreibungThis drug is resistant with respect to a broad spectrum of beta-lactamases. Its spectrum of activity is analogous to that of the third-generation cephalosporin cefotaxime (32.1.2.56), although it is more active with respect to some staphylococci, enterococci, and also a few enterobacteria. Synonyms of this drug are cefrom, cedixen, and others.

VerwendenCephalosporin antibiotic Claforan

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
上海莉凯化工技术有限公司16628776521 · [email protected]
深圳市健竹科技有限公司0755-89218110 13480856786
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]

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