Ciclacillin

Cyclacillin

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 Y
ATC code	None
PubChem	CID 19003
DrugBank	DB01000
ChemSpider	17941 Y
UNII	72ZJ154X86 Y
KEGG	D01334 Y
ChEBI	CHEBI:31444 Y
ChEMBL	CHEMBL1200356 N
Chemical data
Formula	C15H23N3O4S
Mol. mass	341.425 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:HGBLNBBNRORJKI-WCABBAIRSA-N Y
N(what is this?)  (verify)

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Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States.^[5]

References

1. ^ 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. 
2. ^ 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. 
3. ^ 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. 
4. ^ 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. 
5. ^ 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.

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. 

Penems

Faropenem

Carbapenems

Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem

Cephalosporins/
(cephems)

1st (PEcK)	Cefazolin# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole
2nd (HEN)	Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)
3rd	Cefixime# • Ceftriaxone# • antipseudomonal (Ceftazidime# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ‡)
4th (antips-)	Cefepime • Cefozopran • Cefpirome • Cefquinome
5th	Ceftobiprole • Ceftaroline fosamil
Veterinary	Ceftiofur • Cefquinome • Cefovecin

Monobactams

Aztreonam • Tigemonam • Carumonam • Tabtoxin

β-lactamase inh.

penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)

Combinations

Amoxicillin/clavulanic acid^# • Imipenem/cilastatin^# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam

Other

polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: BAC bact (clas) gr+f/gr+a(t)/gr-p(c)/gr-o drug(J1p, w, n, m, vacc)