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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H28N2O7S
Molecular Weight 440.511
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Tacapenem pivoxil

SMILES

C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(S[C@H]3CNC(=O)C3)=C(N2C1=O)C(=O)OCOC(=O)C(C)(C)C

InChI

InChIKey=ZNOVVAJWYUBFMI-JIFFNSBPSA-N
InChI=1S/C20H28N2O7S/c1-9-14-13(10(2)23)17(25)22(14)15(16(9)30-11-6-12(24)21-7-11)18(26)28-8-29-19(27)20(3,4)5/h9-11,13-14,23H,6-8H2,1-5H3,(H,21,24)/t9-,10-,11-,13-,14-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H28N2O7S
Molecular Weight 440.511
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

CS-834 is a beta-lactam antibiotic of a carbapenem class, developed by the Japanese company Sankyo Co. Ltd. CS-834 is an ester-type prodrug of the active metabolite R-95867. The drug showed potent and well balanced antibacterial activity as well as stability against dehydropeptidase-I. The in vivo efficacy of CS-834 was evaluated in murine systemic infections caused by 16 strains of gram-positive and -negative pathogens. The efficacy of CS-834 was in many cases superior to those of cefteram pivoxil, cefpodoxime proxetil, cefdinir, and cefditoren pivoxil, especially against infections caused by S. aureus, penicillin-resistant S. pneumoniae, E. coli, Citrobacter freundii, and Proteus vulgaris. Pharmacokinetics of CS-834 was evaluated in healthy male volunteers, but no further clinical development of the drug was reported.

Approval Year

PubMed

PubMed

TitleDatePubMed
Crystal structure of a 1beta-methylcarbapenem antibiotic, pivaloyloxymethyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[[(R)-5-oxopyrrolidin-3-yl]thio]-1-carbapen-2-em-3-carboxylate, CS-834 dihydrate.
2001-02
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:58:58 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:58 GMT 2025
Record UNII
H26S03B779
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Tacapenem pivoxil
Common Name English
CS-834
Preferred Name English
CS834
Code English
1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID, 6-((1R)-1-HYDROXYETHYL)-4-METHYL-7-OXO-3-(((3R)-5-OXO-3-PYRROLIDINYL)THIO)-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER, (4R,5S,6S)-
Systematic Name English
Code System Code Type Description
EVMPD
SUB121726
Created by admin on Mon Mar 31 17:58:58 GMT 2025 , Edited by admin on Mon Mar 31 17:58:58 GMT 2025
PRIMARY
FDA UNII
H26S03B779
Created by admin on Mon Mar 31 17:58:58 GMT 2025 , Edited by admin on Mon Mar 31 17:58:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID30935699
Created by admin on Mon Mar 31 17:58:58 GMT 2025 , Edited by admin on Mon Mar 31 17:58:58 GMT 2025
PRIMARY
CAS
157542-49-9
Created by admin on Mon Mar 31 17:58:58 GMT 2025 , Edited by admin on Mon Mar 31 17:58:58 GMT 2025
PRIMARY
PUBCHEM
177994
Created by admin on Mon Mar 31 17:58:58 GMT 2025 , Edited by admin on Mon Mar 31 17:58:58 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY