バカンピシリン

Bacampicillin

HCID 441397CAS 50972-17-3
部分構造検索類似構造を探す

基本情報

標準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
分子式
C21H27N3O7S
平均分子量
465.5 g/mol
単同位体質量
465.1569712

概要

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.

名称と識別子

優先名称
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
現地名
バカンピシリン
英語名
BACAMPICILLIN
分子式
C21H27N3O7S
分子量
465.52

名称と別名

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
名称をさらに表示
バカンピシリン6α-[[(R)-2-アミノ-2-フェニルアセチル]アミノ]ペニシラン酸1-[(エトキシカルボニル)オキシ]エチル(2S,5R,6R)-6-[[(2R)-2-アミノ-2-フェニルアセチル]アミノ]-3,3-ジメチル-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2-カルボン酸1-(エトキシカルボニルオキシ)エチル(2S,5β)-6α-[[(R)-アミノフェニルアセチル]アミノ]-3,3-ジメチル-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2β-カルボン酸1-[(エトキシカルボニル)オキシ]エチル1-[(エトキシカルボニル)オキシ]エチル (2S,5R,6R)-6-[(2R)-2-アミノ-2-フェニルアセトアミド]-3,3-ジメチル-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2-カルボキシラート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

データベース識別子

CAS
50972-17-3
PubChem CID
441397
DTXSID
DTXSID2048030
ChEMBL
CHEMBL1583
ChEBI
CHEBI:2968
UNII
8GM2J22278
Nikkaji
J14.626I

物性

構造計算による物性

XLogP
2.7
極性表面積
163 Ų
水素結合供与体数
2
水素結合受容体数
9
回転可能結合数
10
重原子数
32

実験および物理化学的性質

DrugsPharmaceuticals -> Antibiotics
Solubility1.23e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
Melting Point171-176
Physical DescriptionSolid

物理化学的性質

沸点
678.4 · 678.4±55.0 °C(Predicted)
比重(密度)
1.37 · 1.37±0.1 g/cm3(Predicted)
貯蔵温度
-20 °C · Store at -20°C
溶解性
Soluble in DMSO
酸解離定数(Pka)
6.8 · pKa 6.8 (Uncertain)
CAS データベース
50972 · 50972-17-3

安全と法規制

毒性情報

Drug Induced Liver Injury · 4 件

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

化学と産業

薬理情報

ATC Code · 2 件

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

PharmacodynamicsBacampicillin is a prodrug of ampicillin and is microbiologically inactive.
Mechanism of Action · 1 件

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

応用分野

用途ペニシリン系抗生物質抗菌活性

上流・下流製品情報

サプライヤー18 社

北京华美互利生物化工010-56205725 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13318593351 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]

補足説明

定義ChEBI: A penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin.

関連反応

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