CAS 70797-11-4|Cefpiramido [INN-Spanish]|SM-1652|Cefpiramide|Cefpiramide Sodium|Cefpiramidum [INN-Latin]|(6R)-7-[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1,4-dihydropyridin-3-yl)formamido]acetami...

基本信息

化学结构

分子式

C₂₅H₂₄N₈O₇S₂

分子量

612.63746

精确质量

612.12093715

电荷

0

InChI

InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18?,23-/m1/s1

InChIKey

PWAUCHMQEXVFJR-JIUDAOPXSA-N

Canonic Smiles

Oc1ccc(cc1)[C@H](C(=O)NC1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)NC(=O)c1c[nH]c(cc1=O)C

Isomeric Smiles

S1[C@H]2N(C(=O)C2NC(=O)[C@H](NC(=O)c2c(=O)cc([nH]c2)C)c2ccc(O)cc2)C(=C(C1)CSc1n(nnn1)C)C(=O)O

计算属性

JChem

Acid pKa

3.3837736

质子受体

11

质子供体

5

LogD (pH = 5.5)

-2.3815353

LogD (pH = 7.4)

-3.7226677

Log P

-0.28924468

摩尔折射率

166.5938

极化性

57.50968

极化表面积

208.74

可自由旋转的化学键

9

里宾斯基五规则

false

ALOGPS 2.1

Log P

0.85

LOG S

-4.08

溶解度

5.13e-02 g/l

数据来源

学术数据

数据来源

名称和标识

别名

CefpiramideSM-1652

IUPAC标准名

(6R)-7-[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1,4-dihydropyridin-3-yl)formamido]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

IUPAC传统名

cefpiramide

商标名

Cefpiramido [INN-Spanish]Cefpiramide [USAN:INN]Cefpiramide SodiumCefpiramidum [INN-Latin]

名称和标识

数据登录号

CAS号

70797-11-4

PubChem CID

107654

PubChem SID

160963776

数据登录号

化合物性质

理化性质

疏水性(logP)

-0.9

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00430

Drug Groups

approved

Description

Cefpiramide is a third-generation cephalosporin antibiotic.

Indication

For treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.

Pharmacology

Cefpiramide is a cephalosporin active against Pseudomonas aeruginosa. It has a broad spectrum of antibacterial activity. Cefpiramide works by inhibiting bacterial cell wall biosynthesis. The plasma half-lives of cefpiramide in rabbits, dogs, and rhesus monkeys were much longer than those of cefoperazone and cefazolin.

Toxicity

Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.

Affected Organisms

Enteric bacteria and other eubacteria

Absorption

Rapidly absorbed following intramuscular injection.

Half Life

4.44 hours

References

• Wang H, Yu Y, Xie X, Wang C, Zhang Y, Yuan Y, Zhang X, Liu J, Wang P, Chen M: In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China. J Infect Chemother. 2000 Jun;6(2):81-5. [Pubmed]

• Iakovlev VP, Vishnevskii VA, Khlebnikov EP, Khadin IM, Plavlova MV, Elagina LV, Izotova GN: [Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery] Antibiot Khimioter. 1995 Sep;40(9):30-4. [Pubmed]

• Sampi K, Hattori M: [Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective study] Gan To Kagaku Ryoho. 1992 Aug;19(9):1315-20. [Pubmed]

External Links

• [Wikipedia]

描述信息

参考文献

PubChem文献

数据源提供

• Sampi K, Hattori M: [Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective study] Gan To Kagaku Ryoho. 1992 Aug;19(9):1315-20. Pubmed

• Iakovlev VP, Vishnevskii VA, Khlebnikov EP, Khadin IM, Plavlova MV, Elagina LV, Izotova GN: [Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery] Antibiot Khimioter. 1995 Sep;40(9):30-4. Pubmed

• Wang H, Yu Y, Xie X, Wang C, Zhang Y, Yuan Y, Zhang X, Liu J, Wang P, Chen M: In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China. J Infect Chemother. 2000 Jun;6(2):81-5. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性

化合物信息

ID:313