U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H29N5O8S2
Molecular Weight 567.635
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFCAPENE PIVOXIL

SMILES

[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=C/CC)\C3=CSC(N)=N3)C(=O)OCOC(=O)C(C)(C)C

InChI

InChIKey=WVPAABNYMHNFJG-QDVBXLKVSA-N
InChI=1S/C23H29N5O8S2/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29)/b12-6-/t14-,18-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18347113 | https://www.ncbi.nlm.nih.gov/pubmed/26440444

Cefcapene is a semisynthetic third-generation cephalosporin with antibacterial activity. Cefcapene binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Giasion

Approved Use

GIASION is indicated for treatment of the following infections caused by susceptible microorganisms: (see section 5.1 pharmacodynamic properties): Pharyngo-acute tonsillitis Acute maxillary sinusitis Acute exacerbation of chronic bronchitis Community acquired pneumonia, mild or moderate Infections uncomplicated skin and skin structures, such as cellulitis, wound infections, abscesses, folliculitis, impetigo and boils.
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Comparison of the efficacies of oral beta-lactams in selection of Haemophilus influenzae transformants with mutated ftsI genes.
2008 May
Patents

Sample Use Guides

Oral antibiotic therapy (CFPN-PI (CEFCAPENE), 300 mg/day) were started, resulting in gradual improvement of the skin lesion to a PPPASI score of 1 and a VAS score of 2.2 after 2 months
Route of Administration: Oral
A spontaneous rifampin-resistant H. influenzae Rd clone, designated RdRIF (19), and two BLNAR isolates (MSC06647 and MSC06663) were used in this study. Cefcapene activity was determined by the broth dilution method. Cefcapene shows potent antimicrobial activity with MIC 0.008mg/ml (for RdRIF), 0.25mg/ml (for MSC06647) and 2 mg/ml (for MSC06663).
Name Type Language
CEFCAPENE PIVOXIL
WHO-DD  
Common Name English
Cefcapene pivoxil [WHO-DD]
Common Name English
CEFCAPENE PIVALOYLOXYMETHYL ESTER [MI]
Common Name English
2,2-DIMETHYLPROPANOYLOXYMETHYL (6R,7R)-7-(((Z)-2-(2-AMINO-1,3-THIAZOL-4-YL)PENT-2-ENOYL)AMINO)-3-(CARBAMOYLOXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE
Systematic Name English
CEFCAPENE PIVALOYLOXYMETHYL ESTER
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
Code System Code Type Description
SMS_ID
100000084982
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
PUBCHEM
5282438
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
MERCK INDEX
m3190
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
532
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
WIKIPEDIA
Cefcapene pivoxil
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
FDA UNII
8I8MJ56XFQ
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID7049134
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
NCI_THESAURUS
C98218
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
EVMPD
SUB01110MIG
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY
CAS
105889-45-0
Created by admin on Fri Dec 15 16:44:44 GMT 2023 , Edited by admin on Fri Dec 15 16:44:44 GMT 2023
PRIMARY