CAS 62893-19-0|(6R,7R)-7-{2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido}-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-...

基本信息

化学结构

分子式

C₂₅H₂₇N₉O₈S₂

分子量

645.66738

精确质量

645.14240087

电荷

InChI

InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15?,16-,22-/m1/s1

InChIKey

GCFBRXLSHGKWDP-WTKTZPJXSA-N

Canonic Smiles

CCN1CCN(C(=O)C1=O)C(=O)NC(c1ccc(cc1)O)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C

Isomeric Smiles

S1[C@H]2N(C(=O)[C@H]2NC(=O)C(NC(=O)N2CCN(C(=O)C2=O)CC)c2ccc(O)cc2)C(=C(C1)CSc1n(nnn1)C)C(=O)O

计算属性

JChem

Acid pKa

3.3837204

质子受体

质子供体

LogD (pH = 5.5)

-3.0036721

LogD (pH = 7.4)

-4.3111243

Log P

-0.9004894

摩尔折射率

169.0571

极化性

59.325363

极化表面积

220.26

可自由旋转的化学键

里宾斯基五规则

false

ALOGPS 2.1

Log P

-0.11

LOG S

-3.35

溶解度

2.86e-01 g/l

数据来源

学术数据

数据来源

名称和标识

IUPAC标准名

(6R,7R)-7-{2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido}-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

别名

CefoperazoneCefoperazonum [inn-latin]Cefoperazono [inn-spanish]

商标名

Cefobid

IUPAC传统名

(6R,7R)-7-[2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

名称和标识

数据登录号

PubChem SID

46504543160964626

CAS号

62893-19-0

PubChem CID

44185

数据登录号

化合物性质

理化性质

疏水性(logP)

-0.74 [HANSCH,C ET AL. (1995)]

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

DrugBank

DB01329

Drug Groups

approved

Description

Semisynthetic broad-spectrum cephalosporin with a tetrazolyl moiety that is resistant to beta-lactamase. It has been proposed especially against Pseudomonas infections.

Indication

For the treatment of bacterial infections caused by susceptible microorganisms.

Pharmacology

Cefoperazone is a third generation cephalosporin antibiotic. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis

Toxicity

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

No significant quanitity of metabolites have been identified in urine.

Half Life

The mean serum half-life is approximately 2.0 hours, independent of the route of administration.

Protein Binding

The degree of reversible protein binding varies with the serum concentration from 93% at 25 mcg/mL to 90% at 250 mcg/mL and 82% at 500 mcg/mL. Cefotetan is 88% plasma protein bound.

Elimination

Cefoperazone is excreted mainly in the bile.

References

• Jones RN, Barry AL: Cefoperazone: a review of its antimicrobial spectrum, beta-lactamase stability, enzyme inhibition, and other in vitro characteristics. Rev Infect Dis. 1983 Mar-Apr;5 Suppl 1:S108-26. [Pubmed]

External Links

• [Wikipedia]

描述信息

参考文献

PubChem文献

数据源提供

参考文献

生物活性

PubChem BioAssay

生物活性

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