CAS 4697-36-3|Carboxybenzylpenicillin|Carboxybenzylpenicillin acid|Carbenicilline [INN-French]|Carbenicillin|carbenicillin|Pyopen|Carbenicilina [INN-Spanish]|Geopen|Carbenicillina [DCIT]|Carbenicill...

基本信息

化学结构

分子式

C₁₇H₁₈N₂O₆S

分子量

378.39962

精确质量

378.08855731

电荷

InChI

InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1

InChIKey

FPPNZSSZRUTDAP-UWFZAAFLSA-N

Canonic Smiles

O=C(C(c1ccccc1)C(=O)O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C

Isomeric Smiles

S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)C(c1ccccc1)C(=O)O

计算属性

JChem

Acid pKa

3.1068087

质子受体

质子供体

LogD (pH = 5.5)

-3.1951313

LogD (pH = 7.4)

-5.9115877

Log P

0.81535685

摩尔折射率

90.8195

极化性

35.8031

极化表面积

124.01

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

1.13

LOG S

-2.99

溶解度

3.90e-01 g/l

数据来源

学术数据

产品目录

数据来源

名称和标识

商标名

GeopenPyopen

别名

Carbenicillinum [INN-Latin]Carboxybenzylpenicillin acidCarboxybenzylpenicillinCarbenicilline [INN-French]CarbenicillinCarbenicillina [DCIT]Carbenicilina [INN-Spanish]alpha-Carboxybenzylpencillinα-Carboxybenzylpenicillin 溶液α-Carboxybenzylpenicillin solution羧苄青霉素Carbenicillin羧苄青霉素克雷伯氏菌选择性添加剂Klebsiella Selective SupplementCarbenicillin

IUPAC标准名

(2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

IUPAC传统名

carbenicillin

名称和标识

数据登录号

PubChem CID

20824

CAS号

4697-36-3

PubChem SID

4650565316096392324892425

MDL号

MFCD00242604

EC号

225-171-0

数据登录号

化合物性质

理化性质

疏水性(logP)

1.8

溶解度

451 mg/L

闪点

40 °C

104 °F

产品相关信息

无菌消毒

0.2 μm filtered

浓度

100 mg/mL in ethanol/water

Empirical Formula (Hill Notation)

C17H18N2O6S

运输包装

wet ice

有效期

(limited shelf life, expiry date on the label)

级别

for microbiology

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

DrugBank

DB00578

Drug Groups

approved

Description

Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. [PubChem]

Indication

For the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria.

Pharmacology

Carbenicillin is a semisynthetic penicillin. Though carbenicillin provides substantial in vitro activity against a variety of both gram-positive and gram-negative microorganisms, the most important aspect of its profile is in its antipseudomonal and antiproteal activity. Because of the high urine levels obtained following administration, carbenicillin has demonstrated clinical efficacy in urinary infections due to susceptible strains of: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Morganella morganii, Pseudomonas species, Providencia rettgeri, Enterobacter species, and Enterococci (S. faecalis).

Toxicity

Carbenicillin blood levels achievable are very low, and toxic reactions as a function of overdosage should not occur systematically. The oral LD₅₀ in mice is 3,600 mg/kg, in rats 2,000 mg/kg, and in dogs is in excess of 500 mg/kg. The lethal human dose is not known. Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Minimal.

Absorption

Rapidly absorbed from the small intestine following oral administration. Oral bioavailability is 30 to 40%.

Half Life

1 hour

Protein Binding

30 to 60%

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

C1613

Application
Used for selection of ampr transformed cells. Use to study the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.
Biochem/physiol Actions
羧苄青霉素是氨苄青霉素的类似物，是一种常用的选择剂，它可以结合并抑制细菌细胞壁合成中涉及到的酶。它对耐氨苄青霉素的大多数铜绿假单胞菌分离株以及某些吲哚阳性变形杆菌?均有效。氨苄青霉素及其类似物抗性基因 ampr 编码 β-内酰胺酶。羧苄青霉素比氨苄青霉素对 β-内酰胺酶的敏感性更弱。此外它在低 pH 下具有优异的稳定性。实验表明，用羧苄青霉素替代氨苄青霉素有助于防止卫星菌落的过度生长。有效浓度：50 至 100μg/mL。
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

15821

Components
（每瓶，足够用于 500mL 培养基）羧苄青霉素 25mg
Application
用于选择性分离和检测克雷伯氏菌。
Biochem/physiol Actions
羧苄青霉素是氨苄青霉素的类似物，是一种常用的选择剂，它可以结合并抑制细菌细胞壁合成中涉及到的酶。它对耐氨苄青霉素的大多数铜绿假单胞菌分离株以及某些吲哚阳性变形杆菌?均有效。氨苄青霉素及其类似物抗性基因 ampr 编码 β-内酰胺酶。羧苄青霉素比氨苄青霉素对 β-内酰胺酶的敏感性更弱。此外它在低 pH 下具有优异的稳定性。实验表明，用羧苄青霉素替代氨苄青霉素有助于防止卫星菌落的过度生长。有效浓度：50 至 100μg/mL。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 15821.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

描述信息

参考文献

PubChem文献

暂无数据

点击上传数据

参考文献

生物活性

PubChem BioAssay

生物活性

数据来源

学术数据

产品目录

名称和标识

商标名

GeopenPyopen

别名

IUPAC标准名

(2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

IUPAC传统名

carbenicillin

数据登录号

PubChem CID

20824

CAS号

4697-36-3

PubChem SID

4650565316096392324892425

MDL号

MFCD00242604

EC号

225-171-0

描述信息

DrugBank

DB00578

Drug Groups

approved

Description

Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. [PubChem]

Indication

For the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria.

Pharmacology

Toxicity

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Minimal.

Absorption

Rapidly absorbed from the small intestine following oral administration. Oral bioavailability is 30 to 40%.

Half Life

1 hour

Protein Binding

30 to 60%

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

C1613

15821

参考文献

PubChem文献

暂无数据

点击上传数据

生物活性

PubChem BioAssay

化合物性质

理化性质

疏水性(logP)

1.8

溶解度

451 mg/L

闪点

40 °C

104 °F

产品相关信息

无菌消毒

0.2 μm filtered

浓度

100 mg/mL in ethanol/water

Empirical Formula (Hill Notation)

C17H18N2O6S

运输包装

wet ice

有效期

(limited shelf life, expiry date on the label)

级别

for microbiology

化合物信息

ID:460