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MedicaPharma distributes high-quality active pharmaceutical ingredients (APIs) to hospitals, commercial (compounding) pharmacies, research institutes, and universities worldwide.
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Let us handle your sourcing / supply activities. Highly experienced in sourcing specialty raw pharmaceutical ingredients from niche GMP manufacturers around the world.
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Product Description
Mechanism of action
Carfecilline is a carboxypenicillin-class β‑lactam antibiotic and prodrug of carbenicillin. After enzymatic hydrolysis, it releases active carbenicillin, which binds to bacterial penicillin‑binding proteins (PBPs), inhibiting transpeptidase activity required for peptidoglycan crosslinking. This leads to weakening of the bacterial cell wall, osmotic instability and eventual lysis. Carfecilline improves oral bioavailability of carbenicillin and provides broader stability in gastrointestinal environments.
Benefits and advantages
Applied in gram‑negative antibacterial research, β‑lactam SAR studies, PBP‑binding assay development, oral‑prodrug pharmacokinetics research, antipseudomonal susceptibility testing and biofilm‑growth inhibition studies. Useful in modelling prodrug activation mechanisms in β‑lactams.
Side effects and risks
Risks include hypersensitivity reactions typical of β‑lactams, platelet dysfunction, hepatic enzyme shifts and GI irritation. Handle as an antimicrobial β‑lactam with allergy‑risk precautions.
Datasheet
| Molecular Formula | C23H22N2O6S |
|---|---|
| Molecular Weight | 454.5 g/mol |
| CAS Number | 27025-49-6 |
| Storage Condition | Store in a cool, dry place. Keep container tightly closed. Protect from moisture and light. |
| Solubility | Solubility depends on solvent and conditions (e.g., pH). Please contact us for solvent-specific guidance. |
| Purity | Purity information is available upon request (COA). |
| Synonym | Carfecillin; Carbenicillin phenyl; Carfecilina; Carfecilline; Carbenicillin phenyl ester |
| IUPAC/Chemical Name | (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(3-oxo-3-phenoxy-2-phenylpropanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| InChl Key | NZDASSHFKWDBBU-KVMCETHSSA-N |
| InChl Code | InChI=1S/C23H22N2O6S/c1-23(2)17(21(28)29)25-19(27)16(20(25)32-23)24-18(26)15(13-9-5-3-6-10-13)22(30)31-14-11-7-4-8-12-14/h3-12,15-17,20H,1-2H3,(H,24,26)(H,28,29)/t15?,16-,17+,20-/m1/s1 |
| References |
3D Conformer.
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