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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

[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=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
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
[General pharmacology of BMY-28100].
1990 Jul
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:40:22 UTC 2023
Edited
by admin
on Fri Dec 15 17:40:22 UTC 2023
Record UNII
S1SDI2FJIY
Record Status Validated (UNII)
Record Version
  • Download
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
FDA UNII
S1SDI2FJIY
Created by admin on Fri Dec 15 17:40:23 UTC 2023 , Edited by admin on Fri Dec 15 17:40:23 UTC 2023
PRIMARY
CAS
92676-86-3
Created by admin on Fri Dec 15 17:40:23 UTC 2023 , Edited by admin on Fri Dec 15 17:40:23 UTC 2023
PRIMARY
MERCK INDEX
m3213
Created by admin on Fri Dec 15 17:40:23 UTC 2023 , Edited by admin on Fri Dec 15 17:40:23 UTC 2023
PRIMARY Merck Index
PUBCHEM
5281006
Created by admin on Fri Dec 15 17:40:23 UTC 2023 , Edited by admin on Fri Dec 15 17:40:23 UTC 2023
PRIMARY
NCI_THESAURUS
C77188
Created by admin on Fri Dec 15 17:40:23 UTC 2023 , Edited by admin on Fri Dec 15 17:40:23 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY