기본 정보
- 표준 SMILES
CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C- InChIKey
PFOLLRNADZZWEX-FFGRCDKISA-N- 분자식
- C21H27N3O7S
- 평균 분자량
- 465.5 g/mol
- 단동위원소 질량
- 465.1569712
개요
Bacampicillin is a penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin. It has a role as a prodrug. It is functionally related to an ampicillin.
이름 및 식별자
- 우선 이름
- Bacampicillin
- IUPAC
- 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
- 영어명
- BACAMPICILLIN
- 분자식
- C21H27N3O7S
- 분자량
- 465.52
이름 및 동의어
bacampicillin50972-17-3BacampicillineBacampicilinaPenglobebacampicillinumCHEBI:29681-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate8GM2J22278DTXSID20480301'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanatecarampicillin
이름 더 보기
BACAMPICILLIN USP/EP/BPBACAMPICILLIN HCL USP(CRM STANDARD)Bacampicillin (base and/or unspecified salts)6α-[[(R)-2-Amino-2-phenylacetyl]amino]penicillanic acid 1-[(ethoxycarbonyl)oxy]ethyl ester(2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 1-(ethoxycarbonyloxy)ethyl ester4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, (2S,5R,6R)-(2S,5R,6R)-6-[[(2R)-2-amino-1-oxo-2-phenylethyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 1-ethoxycarbonyloxyethyl ester4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, [2S-[2α,5α,6β(S*)]]-
BAPC1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl ester, (2S-(2alpha,5alpha,6beta(S*)))-bacampicillina1-((ethoxycarbonyl)oxy)ethyl (2S,5R,6R)-6-(((2R)-2-amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate1-((ethoxycarbonyl)oxy)ethyl (2S,5R,6R)-6-((2R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-(((2R)-2-amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
데이터베이스 식별자
- CAS
50972-17-3- PubChem CID
- 441397
- DTXSID
DTXSID2048030- ChEMBL
CHEMBL1583- ChEBI
CHEBI:2968- UNII
- 8GM2J22278
- Nikkaji
- J14.626I
물성
구조 계산 물성
- XLogP
- 2.7
- 극성 표면적
- 163 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 10
- 무거운 원자 수
- 32
- 형식 전하
- 0
- 복잡도
- 756
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Antibiotics
Solubility1.23e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
Melting Point171-176
Physical DescriptionSolid
물리화학적 성질
- 끓는 점
- 678.4 · 678.4±55.0 °C(Predicted)
- 밀도
- 1.37 · 1.37±0.1 g/cm3(Predicted)
- 저장 조건
- -20 °C · Store at -20°C
- 용해도
- DMSO에 용해됨
- 산도 계수 (pKa)
- 6.8 · pKa 6.8 (Uncertain)
안전 및 규제
독성 정보
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Bacampicillin
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
화학 및 산업
약리 정보
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
PharmacodynamicsBacampicillin is a prodrug of ampicillin and is microbiologically inactive.
Mechanism of Action
During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionAbsorbed following oral administration.
Cellular LocationsCytoplasm
상·하류 제품 정보
상류 원료
공급사18 곳
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추가 설명
정의ChEBI: A penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin.
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