기본 정보
- CAS
97519-39-6- 표준 SMILES
Nc1nc(/C(=C/CC(=O)O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=CCS[C@H]23)cs1- InChIKey
UNJFKXSSGBWRBZ-BJCIPQKHSA-N- 분자식
- C15H14N4O6S2
- 평균 분자량
- 410.4 g/mol
- 단동위원소 질량
- 410.03547653
개요
Ceftibuten is a third-generation cephalosporin antibiotic with a [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino substituent at the 7 position of the cephem skeleton. An orally-administered agent, ceftibuten is used as the dihydrate to treat urinary-tract and respiratory-tract infections. It has a role as an antibacterial drug. It is a cephalosporin and a dicarboxylic acid.
이름 및 식별자
- 우선 이름
- Ceftibuten
- IUPAC
- (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 현지명
- 세프티부텐
- 영어명
- Ceftibuten
- 분자식
- C15H14N4O6S2
- 분자량
- 410.42
이름 및 동의어
ceftibuten97519-39-6CeftibutenoCeftibuteneCeftibutenumSch 39720cis-ceftibutenSch-397207432-SDTXSID4045925CeftibutinACHN383
이름 더 보기
세프티부텐cephems74327432SCS-1355Cedax：Isocefcis-ceftibutinantibiotic7432s
NSC-758925ACHN-383CHEBI:3510IW71N46B4Y(+)-(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidDTXCID2025925PF-06264006(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
데이터베이스 식별자
- CAS
97519-39-6- PubChem CID
- 5282242
- DTXSID
DTXSID4045925- ChEMBL
CHEMBL1605- ChEBI
CHEBI:3510- UNII
- IW71N46B4Y
- EC Number
- 810-182-0
물성
구조 계산 물성
- XLogP
- -0.3
- 극성 표면적
- 216 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 10
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 27
- 형식 전하
- 0
- 복잡도
- 755
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Solubility7.05e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Physical DescriptionSolid
Collision Cross Section
191.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
188.81 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 끓는 점
- 966 ℃ · 966℃
- 밀도
- 1.75 · 1.75±0.1 g/cm3(Predicted)
- 인화점
- 110 ° · >110°(230°F)
- 저장 조건
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 용해도
- 수용액에 용해됩니다. DMSO에도 용해됨
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 2.99 · 2.99±0.50(Predicted)
- 색상
- 흰색에서 베이지색
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P233, P260, P261, P271, P284, P304+P340, P317, P342+P316, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 35 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
독성 정보
Exposure RoutesRapidly absorbed following oral administration.
Toxicity SummaryCeftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Signs and SymptomsOverdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
ceftibuten
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
안전 데이터
화학 및 산업
약리 정보
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingCeftibuten is 65% bound to plasma proteins. The protein binding is independent of plasma ceftibuten concentration.
PharmacodynamicsCeftibuten is an antibiotic with bactericidal actions.
Mechanism of ActionCeftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Metabolism/Metabolites
A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer.
A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer. Route of Elimination: Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
FDA Pharmacological Classification
IW71N46B4Y
CEFTIBUTEN
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Ceftibuten is a Cephalosporin Antibacterial.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Rapidly absorbed following oral administration.
Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
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