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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

[H][C@]12[C@@H](C)C(S[C@H]3CNC(=O)C3)=C(N1C(=O)[C@]2([H])[C@@H](C)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
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:29:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:29:38 GMT 2023
Record UNII
H26S03B779
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Tacapenem pivoxil
Common Name English
CS834
Code English
CS-834
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
SMS_ID
100000144853
Created by admin on Fri Dec 15 15:29:38 GMT 2023 , Edited by admin on Fri Dec 15 15:29:38 GMT 2023
PRIMARY
EVMPD
SUB121726
Created by admin on Fri Dec 15 15:29:38 GMT 2023 , Edited by admin on Fri Dec 15 15:29:38 GMT 2023
PRIMARY
FDA UNII
H26S03B779
Created by admin on Fri Dec 15 15:29:38 GMT 2023 , Edited by admin on Fri Dec 15 15:29:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID30935699
Created by admin on Fri Dec 15 15:29:38 GMT 2023 , Edited by admin on Fri Dec 15 15:29:38 GMT 2023
PRIMARY
CAS
157542-49-9
Created by admin on Fri Dec 15 15:29:38 GMT 2023 , Edited by admin on Fri Dec 15 15:29:38 GMT 2023
PRIMARY
PUBCHEM
177994
Created by admin on Fri Dec 15 15:29:38 GMT 2023 , Edited by admin on Fri Dec 15 15:29:38 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY