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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N5O6S2
Molecular Weight 453.493
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFCAPENE

SMILES

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

InChI

InChIKey=HJJRIJDTIPFROI-NVKITGPLSA-N
InChI=1S/C17H19N5O6S2/c1-2-3-8(9-6-30-16(18)20-9)12(23)21-10-13(24)22-11(15(25)26)7(4-28-17(19)27)5-29-14(10)22/h3,6,10,14H,2,4-5H2,1H3,(H2,18,20)(H2,19,27)(H,21,23)(H,25,26)/b8-3-/t10-,14-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H19N5O6S2
Molecular Weight 453.493
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
2.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Giasion
Primary
Unknown

PubMed

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).
Substance Class Chemical
Record UNII
4D5D3422MW
Record Status Validated (UNII)
Record Version