세페로라존
세페로라존 · CEFOPERAZONE ACID · Cefoperazone (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 acid · 5-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)- · Cefob · l~rdum · Medocef
식별자 및 물리적 특성
| CAS No. | 62893-19-0 |
|---|---|
| 분자식 | C25H27N9O8S2 |
| 평균 분자량 | 645.7 g/mol |
| 단동위원소 질량 | 645.1424012 g/mol |
| SMILES | CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(CSc4nnnn4C)CS[C@H]23)c2ccc(O)cc2)C(=O)C1=O |
| InChIKey | GCFBRXLSHGKWDP-XCGNWRKASA-N |
| PubChem CID | 44187 |
| ChEMBL | CHEMBL507674 |
| ChEBI | CHEBI:3493 |
| EC No. | 263-749-4 |
| DTXSID | DTXSID2022759 |
| 현지명 | 세페로라존 |
화학 및 물리적 성질
| XLogP | -0.7 |
|---|---|
| 극성 표면적 | 271 |
| 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 |
| 의약품 | Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15 |
| LogP(분배 계수) | -0.74 |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsCephalosporinsPharmaceuticals |
| Animal Drugs | Pharmaceuticals -> UK Veterinary Medicines Directorate List |
| 녹는점 | 188-190169-171 C |
| Collision Cross Section | 239.1 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]238.72 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 밀도 | 1.77±0.1 g/cm3(Predicted) |
| 저장 조건 | 2-8°C |
| 용해도 | DMSO(약간 용해됨, 초음파 처리), 메탄올(약간 용해됨, 가열, 초음파 처리) |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | pKa 2.6 (Uncertain) |
| 색상 | 흰색에서 황백색까지 |
| Merck | 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 | DangerH317 (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. |
|---|---|
| 규제 정보 | REACH registered substance: Cefoperazone (EC: 263-749-4) |
| 기타 안전 정보 | 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 Categories | Skin Sens. 1 (100%) |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)cefoperazoneDILI PositiveIntravenousDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| RTECS 번호 | XI0373900 |
| 관세 코드 | 29419000 |
| 위험 문구(R) | 20/21/22-36/37/38 |
| 위험 표시 | Xn |
| 안전 문구(S) | 26-36 |
용도
개요
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.
용도
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.