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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 of CEFPROZIL ANHYDROUS, (E)-

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

Description

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).

Approval Year

PubMed

PubMed

TitleDatePubMed
[General pharmacology of BMY-28100].
1990 Jul
Pharmacokinetics of cefprozil in infants and children.
1990 Nov
Patents

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
Name Type Language
CEFPROZIL ANHYDROUS, (E)-
Common Name English
BBS-1067
Code 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
CAS
92676-86-3
Created by admin on Tue Mar 06 17:05:28 UTC 2018 , Edited by admin on Tue Mar 06 17:05:28 UTC 2018
PRIMARY
MERCK INDEX
M3213
Created by admin on Tue Mar 06 17:05:28 UTC 2018 , Edited by admin on Tue Mar 06 17:05:28 UTC 2018
PRIMARY Merck Index
PUBCHEM
5281006
Created by admin on Tue Mar 06 17:05:28 UTC 2018 , Edited by admin on Tue Mar 06 17:05:28 UTC 2018
PRIMARY SWITZERF
NCI_THESAURUS
C77188
Created by admin on Tue Mar 06 17:05:28 UTC 2018 , Edited by admin on Tue Mar 06 17:05:28 UTC 2018
PRIMARY