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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 of CEFPROZIL, (E)-

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

Description
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

Curator's Comment: # Bristol-Myers Squibb

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

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
Curator's Comment: E (trans) cefprozil isomer demostrates antibacterial activity against Staphylococcus aureus and Escherichia coli however to a lesser extent than mixture of cefprozil isomers (cis 90%, trans 9%)
Unknown
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
Created by admin on Fri Dec 15 15:53:30 GMT 2023 , Edited by admin on Fri Dec 15 15:53:30 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C77189
Created by admin on Fri Dec 15 15:53:30 GMT 2023 , Edited by admin on Fri Dec 15 15:53:30 GMT 2023
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RS_ITEM_NUM
1098049
Created by admin on Fri Dec 15 15:53:30 GMT 2023 , Edited by admin on Fri Dec 15 15:53:30 GMT 2023
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CAS
111900-24-4
Created by admin on Fri Dec 15 15:53:30 GMT 2023 , Edited by admin on Fri Dec 15 15:53:30 GMT 2023
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PUBCHEM
6436628
Created by admin on Fri Dec 15 15:53:30 GMT 2023 , Edited by admin on Fri Dec 15 15:53:30 GMT 2023
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FDA UNII
3ADV90MJVU
Created by admin on Fri Dec 15 15:53:30 GMT 2023 , Edited by admin on Fri Dec 15 15:53:30 GMT 2023
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