CAS 62893-19-0 Cefoperazone (HCID 44187)

概要

Cefoperazone is a semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance. It has a role as an antibacterial drug.

名称と識別子

優先名称: Cefoperazone
IUPAC: (6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
現地名: セフォペラゾン
英語名: Cefoperazone
分子式: C25H27N9O8S2
分子量: 645.67

名称と別名

cefoperazone62893-19-0CefoperazonumCefoperazonoPeracefCefoperazonCefoperazonaCHEBI:34937U75I1278DDTXSID2022759(6R,7R)-7-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinylcarboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure(6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

名称をさらに表示

セフォペラゾンセフォペラゾン ACIDセホビドセホペラゾンセホブセフォペラジン(6R,7R)-7-[(2R)-2-[(4-エチル-2,3-ジオキソピペラジン-1-カルボニル)アミノ]-2-(4-ヒドロキシフェニル)アセトアミド]-3-{[(1-メチル-1H-1,2,3,4-テトラゾール-5-イル)スルファニル]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-カルボン酸(6R,7R)-7-[(R)-2-[(4-エチル-2,3-ジオキソピペラジン-1-イル)カルボニルアミノ]-2-(4-ヒドロキシフェニル)アセチルアミノ]-3-[[(1-メチル-1H-テトラゾール-5-イル)チオ]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-カルボン酸セホペラジン(6R,7R)-7α-[(R)-2-[(4-エチル-2,3-ジオキソピペラジン-1-イル)カルボニルアミノ]-2-(4-ヒドロキシフェニル)アセチルアミノ]-3-[[(1-メチル-1H-テトラゾール-5-イル)チオ]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-カルボン酸CEFOPERAZONE ACIDCefoperazone (Cefobid)(6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-(4-hydroxyphenyl)acetyl]aMino]-3-[[(1-Methyl-1H-tetrazol-5-yl)thio]Methyl]-8-oxo-,(6R,7R)-Cefobl~rdumMedocefcefoperazineCephaperazon

(6R,7R)-7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)(4-hydroxyphenyl)acetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6-alpha,7-beta(R*)))-(6R,7R)-7-(((2R)-2-((4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino)-2-(4-hydroxyphenyl)acetyl)amino)-3-((1-methyltetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-((2-((4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino)-2-(4-hydroxyphenyl)acetyl)amino)-3-((1-methyltetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:918190DTXCID702759J01DA32263-749-4

データベース識別子

CAS: 62893-19-0
PubChem CID: 44187
DTXSID: DTXSID2022759
ChEMBL: CHEMBL507674
ChEBI: CHEBI:3493
UNII: 7U75I1278D
EC Number: 263-749-4
Nikkaji: J19.295C

物性

構造計算による物性

XLogP: -0.7
極性表面積: 271 Å²
水素結合供与体数: 4
水素結合受容体数: 13
回転可能結合数: 9
重原子数: 44
形式電荷: 0
複雑度: 1,250

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

LogP-0.74

Human Drugs · 2 件

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins

Pharmaceuticals

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List

Melting Point188-190

Collision Cross Section · 2 件

239.1 Å² [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

238.72 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 169 · 169-171 C
比重(密度): 1.77 · 1.77±0.1 g/cm3(Predicted)
貯蔵温度: 2 · 2-8°C
溶解性: DMSO（わずかに、超音波処理）、メタノール（わずかに、加熱、超音波処理）
外見: 個体
酸解離定数(Pka): 2.6 · pKa 2.6 (Uncertain)
色: ホワイトからオフホワイト
Merck: 14 · 14,1930
InChIKey: GCFBRXLSHGKWDP-XCGNWRKASA-N
SMILES: N12[C@@]([H])([C@H](NC([C@H](NC(N3CCN(CC)C(=O)C3=O)=O)C3=CC=C(O)C=C3)=O)C1=O)SCC(CSC1N(C)N=NN=1)=C2C(O)=O
CAS データベース: 62893 · 62893-19-0(CAS DataBase Reference)

化学的性質

化学的特性white crystals

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationREACH registered substance: Cefoperazone (EC: 263-749-4)

Other Safety Information · 1 件

IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Environment tier I assessment

Hazard Classes and CategoriesSkin Sens. 1 (100%)

毒性情報

Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefoperazone

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

rtecs: XI0373900
hs_code: 29419000
risk_code: 20/21/22-36/37/38
hazard_code: Xn
safety_code: 26-36

化学と産業

薬理情報

ATC Code · 3 件

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingThe degree of reversible protein binding varies with the serum concentration from 93% at 25 mcg/mL to 90% at 250 mcg/mL and 82% at 500 mcg/mL. Cefotetan is 88% plasma protein bound.

PharmacodynamicsCefoperazone is a third generation cephalosporin antibiotic. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis

Mechanism of Action · 1 件

Like all beta-lactam antibiotics, cefoperazone binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

Biological Half-LifeThe mean serum half-life is approximately 2.0 hours, independent of the route of administration.

Metabolism/MetabolitesNo significant quanitity of metabolites have been identified in urine.

用途と製造

Use ClassificationPharmaceuticals

応用分野 · 2 件

説明Cefoperazone has a C-7 side chain reminiscent of piperacillin's and also possesses the C-3 side chain (MTT ) that often is associated with the bleeding and alcohol intolerance problems among patients taking cephalosporins. Its useful activity against pseudomonads partly compensates for this, although it is not potent enough to be used as a single agent against this difficult pathogen. The C-7 side chain does not convey sufficient resistance to many β-lactamases, although the addition of clavulanic acid or sulbactam would presumably help.

使用Cefoperazone also has a broad spectrum of antimicrobial action, including most clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is stable with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria. Cefoperazone is used for bacterial infections of the lower respiratory tract, urinary and sexual tracts, bones, joints, skin, soft tissues, abdominal, and gynecological infections. Synonyms of this drug are cefazon, cefobid, cefobis, and many others.

上流・下流製品情報

上流原料

1-フェニル-5-メルカプト-1H-テトラゾール 4'-ヒドロキシアセトアニリドピラジン窒素アセトン p-トルエンスルホン酸一水和物テトラゾールクロロトリメチルシラン Acid chloride 5-メルカプト-1-メチルテトラゾール N,N-ジメチルアセトアミド 1-[(2S)-3-(アセチルチオ)-2-メチルプロピオニル]-L-プロリン水和物

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国药集团化学试剂有限公司86-21-63210123 · [email protected]

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济南百隆化学有限公司[email protected] · [email protected]

HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]

補足説明

定義ChEBI: A semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance.

化合物ノート

読み込み中…

セフォペラゾン

基本情報

概要