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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
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
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