CAS 62893-19-0 Cefoperazone (HCID 44187)

개요

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

이름 및 식별자

우선 이름: 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
현지명: 세페로라존
영어명: Cefoperazone
분자식: C25H27N9O8S2
분자량: 645.67

이름 및 동의어

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

이름 더 보기

세페로라존CEFOPERAZONE 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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: -0.7
극성 표면적: 271 Å²
수소 결합 공여자 수: 4
수소 결합 수용자 수: 13
회전 가능 결합 수: 9
무거운 원자 수: 44
형식 전하: 0
복잡도: 1,250

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

LogP-0.74

Human Drugs · 2건

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 · 2건

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]

물리화학적 성질

녹는점: 169 · 169-171 C
밀도: 1.77 · 1.77±0.1 g/cm3(Predicted)
저장 조건: 2 · 2-8°C
용해도: DMSO(약간 용해됨, 초음파 처리), 메탄올(약간 용해됨, 가열, 초음파 처리)
물리적 상태: 고체
산도 계수 (pKa): 2.6 · pKa 2.6 (Uncertain)
색상: 흰색에서 황백색까지
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

화학적 성질

white crystals

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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

Other Safety Information · 1건

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%)

독성 정보

Drug Induced Liver Injury · 5건

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

안전 데이터

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

화학 및 산업

약리 정보

ATC Code · 3건

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 · 1건

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.

용도 및 제조

Use ClassificationPharmaceuticals

응용 분야 · 2건

개요Cefoperazone 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.

용도Cefoperazone 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.

상·하류 제품 정보

상류 원료

1-페닐-1H-테트라졸-5-티올 아세트아미노펜 Pyrazine 질소 아세톤 p-토루엔 술폰산 일수화물 1H-테트라졸 트리메틸클로로실란 Acid chloride 5-머캅토-1-메틸테트라졸 N,N-디메틸아세트아미드 (2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline

공급사100 곳

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

北京华美互利生物化工010-56205725 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

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

HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]

추가 설명

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

화합물 노트

불러오는 중…

세페로라존

기본 정보

개요