CEFPIMIZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H26N6O10S2
Molecular Weight	670.67
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=C(NC=N1)C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SCC(C[N+]4=CC=C(CCS([O-])(=O)=O)C=C4)=C(N3C2=O)C(O)=O)C5=CC=CC=C5

InChI

InChIKey=LNZMRLHZGOBKAN-KAWPREARSA-N

InChI=1S/C28H26N6O10S2/c35-23(18(16-4-2-1-3-5-16)31-24(36)19-20(27(38)39)30-14-29-19)32-21-25(37)34-22(28(40)41)17(13-45-26(21)34)12-33-9-6-15(7-10-33)8-11-46(42,43)44/h1-7,9-10,14,18,21,26H,8,11-13H2,(H5-,29,30,31,32,35,36,38,39,40,41,42,43,44)/t18-,21-,26-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6605719
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/3041630, http://www.ncbi.nlm.nih.gov/pubmed/4032736

Cefpimizole is an antibiotic of broad spectrum developed in Japan for the treatment of such conditions as uncomplicated gonorrhea and gynecologic infections. The drug was tested in clinical trials, however, its development was terminated.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obstetric and gynecologic infections 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4032718	Curative		Phase II 1147	Unknown Approved Use Unknown
Uncomplicated gonorrhea 10 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3041630	Curative		Phase II 1147	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Upregulatory effects of cefpimizole natrium on human leukocytes.	1992-07	1324894
Comparison of cefpimizole with cefotaxime and penicillin G for treatment of uncomplicated gonorrhea.	1988-04-01	3041630
High-performance liquid chromatography measurement of antimicrobial concentrations in polymorphonuclear leukocytes.	1987-12	3439800
Clinical study of cefpimizole in obstetric and gynecologic infections.	1985-04	4032718
Mechanism of action of AC-1370 on phagocyte functions.	1984-01	6703687
In vitro activity and beta-lactamase stability of U-63196E, a novel cephalosporin.	1983-09	6605719
Effects of AC-1370, a new semisynthetic cephalosporin, on phagocyte functions.	1983-06	6614892

Patents

Sample Use Guides

In Vivo Use Guide

1.0 g of cefpimizole (gonorrea treatment).

Route of Administration: Intramuscular

In Vitro Use Guide

In vitro activity of cefpimizole was tested against C. diversus (MIC 0.4-12.5 ug/ml), H. influenzae (MIC 0.1-0.4 ug/ml), N. gonorrhoeae (MIC 0.1-1.6 ug/ml), Proteus mirabilis (MIC 0.2-12.5 ug/ml), Streptococcus pyogenes (MIC 0.4-3.1 ug/ml), Streptococcus bovis (MIC 1.6-3.1 ug/ml), Streptococcus mitis (MIC 0.2-3.1 ug/ml), Streptococcus agalactiae (MIC 0.8-3.1 ug/ml).

Name

Type

Language

CEFPIMIZOLE

Official Name

English

AC-1370

Preferred Name

English

U-63196

Code

English

1-[[(6R,7R)-2-Carboxy-7-[(R)-2-(5-carboxyimidazole-4-carboxamido)-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-4-(2-sulfoethyl)pyridinium hydroxide, inner salt

Common Name

English

cefpimizole [INN]

Common Name

English

U-63,196

Code

English

Cefpimizole [WHO-DD]

Common Name

English

CEFPIMIZOLE [USAN]

Common Name

English

PYRIDINIUM, 1-((2-CARBOXY-7-(((((5-CARBOXY-1H-IMIDAZOL-4-YL)CARBONYL)AMINO)PHENYLACETYL)AMINO)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-4-(2-SULFOETHYL)-, HYDROXIDE, INNER SALT, (6R-(6.ALPHA.,7.BETA.(R*)))-

Common Name

English

CEFPIMIZOLE [MI]

Common Name

English

AC 1370

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C357