セフピロム

Cefpirome

HCID 5479539CAS 84957-29-9

基本情報

標準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
分子式: C22H22N6O5S2
平均分子量: 514.6 g/mol
単同位体質量: 514.1093098

概要

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.

名称と識別子

優先名称: 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
現地名: セフピロム
英語名: Cefpirome
分子式: C22H22N6O5S2
分子量: 514.58

名称と別名

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

名称をさらに表示

セフピロム(6R,7R)-7α-[[(2-アミノ-4-チアゾリル)[(Z)-メトキシイミノ]アセチル]アミノ]-3-[[(6,7-ジヒドロ-5H-シクロペンタ[b]ピリジン-1-イウム)-1-イル]メチル]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボキシラート1-{[(6R,7R)-7-[(2Z)-2-(2-アミノ-1,3-チアゾール-4-イル)-2-(メトキシイミノ)アセトアミド]-2-カルボキシラト-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-3-イル]メチル}-5H,6H,7H-シクロペンタ[b]ピリジン-1-イウム(6R,6β)-7α-[[(2-アミノ-4-チアゾリル)[(Z)-メトキシイミノ]アセチル]アミノ]-8-オキソ-3-[[(6,7-ジヒドロ-5H-1-ピリンジン-1-イウム)-1-イル]メチル]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸イオン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

データベース識別子

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

物性

構造計算による物性

XLogP: 0.9
極性表面積: 207 Å²
水素結合供与体数: 2
水素結合受容体数: 10
回転可能結合数: 6
重原子数: 35
形式電荷: 0
複雑度: 955

実験および物理化学的性質

DrugsPharmaceuticals -> Antibiotics

物理化学的性質

貯蔵温度: 2 · 2-8°C(protect from light)

安全と法規制

毒性情報

Drug Induced Liver Injury · 4 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Cefpirome

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

安全データ

毒性: 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)
risk_code: 36/37/38-42/43
hazard_code: Xi
safety_code: 22-26-36/37/39

化学と産業

薬理情報

ATC Code · 2 件

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.

応用分野 · 2 件

説明This 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.

使用Cephalosporin antibiotic Claforan

上流・下流製品情報

上流原料

ヨウ化カリウム 5-アセトアミド-N,N'-ビス(2,3-ジヒドロキシプロピル)-2,4,6-トリヨードイソフタルアミドセフォタキシム 6,7-Dihydro-5H-cyclopenta[b]pyridine

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