CEFPROZIL, (E)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H19N3O5S.H2O
Molecular Weight	407.441
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[H][C@]12SCC(\C=C\C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(O)=O

InChI

InChIKey=ALYUMNAHLSSTOU-CIRGZYLNSA-N

InChI=1S/C18H19N3O5S.H2O/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);1H2/b3-2+;/t12-,13-,17-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 2578

PubMed

Title	Date	PubMed

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 `Fri Dec 15 15:53:30 GMT 2023` Edited by `admin` on `Fri Dec 15 15:53:30 GMT 2023`
Record UNII	3ADV90MJVU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFPROZIL, (E)-

Common Name

English

CEFPROZIL, E-ISOMER

Common Name

English

CEFPROZIL, (E)-ISOMER

Common Name

English

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

Systematic Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357