CEFCAPENE PIVOXIL

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8107269
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Penicillin-binding protein 1A 45 Target ID: P02918 Gene ID: 947907.0 Gene Symbol: mrcA Target Organism: Escherichia coli (strain K12) Sources: https://www.jstage.jst.go.jp/article/chemotherapy1953/41/Supplement1/41_Supplement1_102/_article	Inhibitor 8297
Penicillin-binding protein 2a 17 Target ID: CHEMBL3512 Sources: https://www.jstage.jst.go.jp/article/chemotherapy1953/41/Supplement1/41_Supplement1_102/_article	Inhibitor 8297
Beta-lactamase 16 Target ID: CHEMBL2725 Sources: https://www.jstage.jst.go.jp/article/chemotherapy1953/41/Supplement1/41_Supplement1_102/_article	Inhibitor 8297	2.0 nM [Ki]
Penicillin-binding protein 31 Target ID: CHEMBL2363020 Sources: http://www.torrinomedica.it/farmaci/schedetecniche/Giasion.asp#SP10	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tonsillitis 36 Sources: http://www.ndrugs.com/?s=giasion	Curative		Approved 8429	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.
Pustulosis of palm and sole 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26440444	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Comparison of the efficacies of oral beta-lactams in selection of Haemophilus influenzae transformants with mutated ftsI genes.	2008 May	18347113

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357