CICLACILLIN
Ciclacillin is a semisynthetic penicillin antibiotic inhibiting bacterial cell wall synthesis. It is effective for respiratory and urinary infections. Side effects include rash, GI upset, and allergic reactions.
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Product Description
Mechanism of Action
Ciclacillin is an aminopenicillin derivative that inhibits bacterial cell‑wall synthesis by binding PBPs and preventing peptidoglycan crosslinking. It demonstrates improved oral stability relative to ampicillin through structural cyclisation that protects the β‑lactam from hydrolysis.
Benefits and Advantages
Used in β‑lactam stability research, gram‑positive susceptibility studies, oral‑absorption modelling, PBP‑binding assays and aminopenicillin SAR comparisons.
Side Effects and Risks
Risks include allergic reactions, GI upset, hepatic enzyme elevation and alteration of gut flora. Handle following β‑lactam antimicrobial precautions.
Datasheet
| Molecular Formula | C16H23N3O5S |
|---|---|
| Molecular Weight | 341.4 g/mol |
| CAS Number | 3485-14-1 |
| Storage Condition | Store in a cool, dry place. Keep container tightly closed. Protect from moisture and light. |
| Solubility | 1.90e+00 g/L |
| Purity | Purity information is available upon request (COA). |
| Synonym | CYCLACILLIN; ciclacillin; Vastcillin; 3485-14-1; Aminocyclohexylpenicillin |
| IUPAC/Chemical Name | (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| InChl Key | HGBLNBBNRORJKI-WCABBAIRSA-N |
| InChl Code | InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1 |
| References |
3D Conformer.
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