About MedicaPharma
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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Niche API specialist - Pro-active supply partner - High service level - Global network - Logistics according to GDP regulations
Product Description
Mechanism of action
Cefmetazole is a cephamycin-class β‑lactam antibiotic structurally related to cefoxitin. Its 7‑α‑methoxy substituent confers enhanced stability against many plasmid- and chromosomal-mediated β‑lactamases, including certain ESBLs and AmpC enzymes. It binds penicillin-binding proteins (PBPs), inhibiting the transpeptidation step of peptidoglycan synthesis. This disrupts the bacterial cell wall, leading to osmotic lysis. Cefmetazole has strong activity against anaerobes and challenging gram-negative organisms, including some resistant Enterobacteriaceae.
Benefits and advantages
Used in ESBL/AmpC resistance modelling, anaerobic-pathogen studies, cephamycin SAR profiling, PBP-binding research, β‑lactamase inhibition investigations, and polymicrobial infection modelling. Valuable for exploring β‑lactam stability mechanisms in resistant gram-negative populations.
Side effects and risks
Risks include hypersensitivity, GI disturbances, hepatic enzyme elevation, coagulation interference, and selection of resistant strains. Handle under β‑lactam antimicrobial containment protocols.
Datasheet
| Molecular Formula | C15H17N3O6S2 |
|---|---|
| Molecular Weight | 471.5 g/mol |
| CAS Number | 56796-20-4 |
| 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 | cefmetazole; 56796-20-4; Cefmetazolo; Cefmetazolum; (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| IUPAC/Chemical Name | (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| InChl Key | SNBUBQHDYVFSQF-HIFRSBDPSA-N |
| InChl Code | InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1 |
| References |
3D Conformer.
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