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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H18N2O5S
Molecular Weight 326.368
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TACAPENEM

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)=O

InChI

InChIKey=CTEFNVKDRWMZSL-CTNSIQBBSA-N
InChI=1S/C14H18N2O5S/c1-5-10-9(6(2)17)13(19)16(10)11(14(20)21)12(5)22-7-3-8(18)15-4-7/h5-7,9-10,17H,3-4H2,1-2H3,(H,15,18)(H,20,21)/t5-,6-,7-,9-,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C14H18N2O5S
Molecular Weight 326.368
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 Feb
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:40:19 UTC 2023
Edited
by admin
on Fri Dec 15 17:40:19 UTC 2023
Record UNII
5216EI628Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TACAPENEM
INN  
INN  
Official Name English
tacapenem [INN]
Common Name English
R-95867
Code English
R95867
Code English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C76565
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
PRIMARY
PUBCHEM
73302
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
PRIMARY
INN
8235
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID60172994
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
PRIMARY
CAS
193811-33-5
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105522
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
PRIMARY
FDA UNII
5216EI628Q
Created by admin on Fri Dec 15 17:40:19 UTC 2023 , Edited by admin on Fri Dec 15 17:40:19 UTC 2023
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY