CEFPROZIL ANHYDROUS, (E)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H19N3O5S
Molecular Weight	389.426
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C\C=C\C1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C2=O)C(O)=O

InChI

InChIKey=WDLWHQDACQUCJR-ZAMMOSSLSA-N

InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H19N3O5S
Molecular Weight	389.426
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.google.com/patents/WO2002083692A
Curator's Comment: Description was created based on several sources, including http://en.cnki.com.cn/Article_en/CJFDTOTAL-ZKSS200701004.htm | https://www.bmscanada.ca/static/products/en/pm_pdf/CEFZIL_EN_PM.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2232158

Cefprozil, an oral cephalosporin antibiotic, is a mixture of antibiotic BMY-28100 (Z- or cis-isomer) and antibiotic BMY-28167 (E- or trans -isomer), the mixture having a Z- to E- isomer ratio in the range of 89:11 to 94:6. BMY-28167 (E- or trans -isomer) is less active when compared with BMY-28100 or isomeric mixture. There were no remarkable differences in the toxicity of the cis isomer, the trans isomer, or cefprozil (the isomeric mixture).

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Pharmacokinetics of cefprozil in infants and children.	1990-11	2073105
[General pharmacology of BMY-28100].	1990-07	2232158

Patents

Sample Use Guides

In Vivo Use Guide

In rats given either cefprozil (cis/trans isomers in a 9:1 ratio), the cis isomer or the trans isomer at 1500 mg/kg/day by oral gavage for one month, alopecia, salivation, reduced body weight in males, decreased litter weight and increased kidney weight were observed. No clinical pathology or gross or microscopic pathology was observed. There were no remarkable differences in the toxicity of the cis isomer, the trans isomer, or cefprozil (the isomeric mixture) in rats given 1500 mg/kg/day by oral gavage for one month.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:50:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:50:07 GMT 2025`
Record UNII	S1SDI2FJIY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BBS-1067

Preferred Name

English

CEFPROZIL ANHYDROUS, (E)-

Common Name

English

CEFPROZIL [MART.]

Common Name

English

CEFPROZIL E-FORM [MI]

Common Name

English

BMY-28167

Code

English

(6R,7R)-7-((R)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-8-OXO-3-PROPENYL-5-THIA-1-AZABICYCLO(4.2.0)OCT-2(E)-ENE-2-CARBOXYLIC ACID

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2R)-AMINO(4-HYDROXYPHENYL)ACETYL)AMINO)-8-OXO-3-(1E)-1-PROPENYL-,(6R,7R)-

Common Name

English

CEFPROZIL ANHYDROUS, E-ISOMER

Common Name

English

Code System Code Type Description

FDA UNII

S1SDI2FJIY