Cloxacillin

Cloxacillin
Systematic (IUPAC) name


(2S,5R,6R)-6-{[3-(2-chlorophenyl)-5-methyl- oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo- 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade names	Cloxapen
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Oral, IM
Pharmacokinetic data
Bioavailability	37 to 90%
Protein binding	95%
Biological half-life	30 minutes to 1 hour
Excretion	Renal and biliary
Identifiers
CAS Number	61-72-3^Y
ATC code	J01CF02 (WHO) QJ51CF02 QS01AA90
PubChem	CID 6098
DrugBank	DB01147^Y
ChemSpider	5873^Y
UNII	O6X5QGC2VB^Y
KEGG	D07733^Y
ChEBI	CHEBI:49566^Y
ChEMBL	CHEMBL891^Y
Chemical data
Formula	C₁₉H₁₈ClN₃O₅S
Molar mass	435.88 g/mol
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]4SC3(C)C
InChI InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1^Y Key:LQOLIRLGBULYKD-JKIFEVAISA-N^Y
(verify)

Cloxacillin is an antibiotic useful for the treatment of a number of bacterial infections. It is semisynthetic and in the same class as penicillin.

Cloxacillin is used against staphylococci that produce beta-lactamase, due to its large R chain, which does not allow the beta-lactamases to bind. This drug has a weaker antibacterial activity than benzylpenicillin, and is devoid of serious toxicity except for allergic reactions.

Cloxacillin was discovered and developed by Beecham.^[1] It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin. It is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system.^[2]

References

↑ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. Retrieved 18 November 2010.
↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

Antibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular

Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Glycopeptide

Inhibit PG chain elongation: Vancomycin^# (Oritavancin
Telavancin)
Teicoplanin (Dalbavancin)
Ramoplanin

β-lactams/
(Inhibit PBP
cross-links)

Penicillins
(Penams)

Narrow Spectrum

β-lactamase Sensitive (1st Generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡

β-lactamase Resistant (2nd Generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended Spectrum

Aminopenicillins (3rd Generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Metampicillin^‡ Talampicillin^‡) Epicillin^‡

Carboxypenicillins (4th Generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡

Ureidopenicillins (4th Generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡

Other	Mecillinam^‡ (Pivmecillinam^‡) Sulbenicillin^‡

Penems

Faropenem^‡

Carbapenems

Cephalosporins/Cephamycins
(Cephems)

1st Generation (P Ec K)	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin^‡ Cefatrizine^‡

2nd Generation (H E N)	Cefaclor Cefotetan Cephamycin (Cefoxitin Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefminox^‡ Cefonicid^‡ Ceforanide^‡ Cefotiam^‡ Cefbuperazone^‡ Cefuzonam^‡ Cefmetazole)^‡ Carbacephem^‡ (Loracarbef^‡)

3rd Generation	Cefixime^# Ceftriaxone^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefotaxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef^‡ Latamoxef^‡‡)

4th Generation (Pseudomonas)	Cefepime Cefozopran^‡ Cefpirome^‡ Cefquinome^‡

5th Generation	Ceftaroline fosamil Ceftolozane Ceftobiprole^‡

Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase Inhibitors

Combinations

Other

polymyxins/detergent
- Colistin
- Polymyxin B
depolarizing
- Daptomycin
Hydrolyze NAM-NAG
- lysozyme
Gramicidin
Isoniazid
Teixobactin

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

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Cloxacillin

See also

References