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

[H][C@]12SCC(C[N+]3=CC=C(CCS([O-])(=O)=O)C=C3)=C(N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)C4=C(N=CN4)C(O)=O)C5=CC=CC=C5)C(O)=O

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

Molecular Formula	C28H26N6O10S2
Molecular Weight	670.67
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 1132	Unknown Approved Use Unknown
Uncomplicated gonorrhea 9 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3041630	Curative		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Clinical study of cefpimizole in obstetric and gynecologic infections.	1985 Apr	4032718
High-performance liquid chromatography measurement of antimicrobial concentrations in polymorphonuclear leukocytes.	1987 Dec	3439800
Comparison of cefpimizole with cefotaxime and penicillin G for treatment of uncomplicated gonorrhea.	1988 Apr-Jun	3041630
Upregulatory effects of cefpimizole natrium on human leukocytes.	1992 Jul	1324894

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:28:58 GMT 2023` Edited by `admin` on `Fri Dec 15 16:28:58 GMT 2023`
Record UNII	24S58UHU7N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFPIMIZOLE

Official 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

AC 1370

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C357