Ciclacillin
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| Systematic (IUPAC) name | |
| (2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}- 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane- 2-carboxylic acid | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | ? |
| Legal status | ? |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | Moderate |
| Protein binding | <25% |
| Identifiers | |
| CAS number | 3485-14-1  |
| ATC code | None |
| PubChem | CID 19003 |
| DrugBank | DB01000 |
| ChemSpider | 17941 |
| UNII | 72ZJ154X86 |
| KEGG | D01334 |
| ChEBI | CHEBI:31444 |
| ChEMBL | CHEMBL1200356  |
| Chemical data | |
| Formula | C15H23N3O4S |
| Mol. mass | 341.425 g/mol |
| SMILES | eMolecules & PubChem |
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Ciclacillin (INN) or cyclacillin (USAN), trade names Cyclapen, Cyclapen-W, Vastcillin, and others, is an aminopenicillin antibiotic. Its spectrum of activity is similar to that of ampicillin, although it is less susceptible to beta-lactamases than ampicillin and has much higher bioavailability.[1] A large randomized, double-blind clinical trial published in 1978 also showed that ciclacillin is associated with significantly fewer and milder adverse effects than ampicillin;[2] later studies seemed to confirm this improved tolerability, at least in children.[3][4]
Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States.[5]
[edit] References
- ^ Warren GH (1976). "Cyclacillin: microbiological and pharmacological properties and use in chemotherapy of infection - a critical appraisal". Chemotherapy 22 (3-4): 154–82. doi:10.1159/000221924. PMID 773605.
- ^ Gold JA, Hegarty CP, Deitch MW, Walker BR (January 1979). "Double-blind clinical trials of oral cyclacillin and ampicillin". Antimicrob Agents Chemother 15 (1): 55–8. PMC 352600. PMID 371540. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=371540.
- ^ McLinn SE, Goldberg F, Kramer R, Saltstein E, Bomze JP, Deitch MW (October 1982). "Double-blind multicenter comparison of cyclacillin and amoxicillin for the treatment of acute otitis media". J Pediatr 101 (4): 617–21. doi:10.1016/S0022-3476(82)80724-5. PMID 6750067.
- ^ McLinn SE, Kaplan J, West N (1983). "Multicenter comparison of cyclacillin and amoxicillin in the treatment of acute streptococcal pharyngitis". Clin Ther 5 (3): 299–304. PMID 6342785.
- ^ Gorbach SL, Bartlett JG, Blacklow NR (2004). Infectious diseases (3rd ed.). Hagerstown, MD: Lippincott Williams & Wilkins. pp. p. 186. ISBN 0-7817-3371-5. http://books.google.com/?id=_eHyE9lRw7oC. Retrieved on September 7, 2008 through Google Book Search.
[edit] Further reading
- Scheld WM, Sydnor A, Farr B, Gratz JC, Gwaltney JM (September 1986). "Comparison of cyclacillin and amoxicillin for therapy for acute maxillary sinusitis". Antimicrob Agents Chemother 30 (3): 350–3. PMC 180557. PMID 3535660. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=3535660.
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