Cloxacillin

Beta-lactam antibiotic

J01CF02 (WHO) QJ51CF02 (WHO) QS01AA90 (WHO)

Pharmacokinetic dataBioavailability37 to 90%Protein binding95%Elimination half-life30 minutes to 1 hourExcretionkidney and biliaryIdentifiers

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 or 5 methyl 3(2 chlorophenyl)4 isoxazoyl penicillin

CAS Number

61-72-3^Y

PubChem CID

6098

DrugBank

DB01147^Y

ChemSpider

5873^Y

UNII

O6X5QGC2VB

KEGG

D07733^Y

ChEBI

CHEBI:49566^Y

ChEMBL

ChEMBL891^Y

CompTox Dashboard (EPA)

DTXSID5022853

ECHA InfoCard100.000.468

Chemical and physical dataFormulaC₁₉H₁₈ClN₃O₅SMolar mass435.88 g·mol⁻¹3D model (JSmol)

Interactive image

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.^[1] This includes impetigo, cellulitis, pneumonia, septic arthritis, and otitis externa.^[1] It is not effective for methicillin-resistant Staphylococcus aureus (MRSA).^[2] It can be used by mouth and by injection.^[1]

Side effects include nausea, diarrhea, and allergic reactions including anaphylaxis.^[1] Clostridium difficile diarrhea may also occur.^[2] It is not recommended in people who have previously had a penicillin allergy.^[1] Use during pregnancy appears to be relatively safe.^[1] Cloxacillin is in the penicillin family of medications.^[2]

Cloxacillin was patented in 1960 and approved for medical use in 1965.^[3] It is on the World Health Organization's List of Essential Medicines.^[4] It is not commercially available in the United States.^[2]

Mechanism of action

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.^{[citation needed]}

Society and culture

Cloxacillin was discovered and developed by Beecham (now GlaxoSmithKline).^[5]

It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin.^[6]

References

^ ^a ^b ^c ^d ^e ^f World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 98, 100, 110–111, 586, 602, 614, 623. hdl:10665/44053. ISBN 9789241547659.
^ ^a ^b ^c ^d "Cloxacillin (Professional Patient Advice)". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 2016-12-20.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ Greenwood D (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. Archived from the original on 6 June 2013. Retrieved 18 November 2010.
^ Gollakner R (2023-05-09). "Cloxacillin". VCA Animal Hospitals. Retrieved 2023-05-09.

External links

"Cloxacillin". Drug Information Portal. U.S. National Library of Medicine.

Antibacterials active on the cell wall and envelope (J01C-J01D)

Beta-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

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^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Glycopeptides Lipoglycopeptides	Inhibit PG chain elongation: Vancomycin^# (Oritavancin Telavancin) Teicoplanin (Dalbavancin) Ristocetin^‡ Avoparcin Inhibit autolysin: Corbomycin (not approved)
Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Polymyxins	Bind to LPS in the outer bacterial membrane, acting in detergent-like fashion: Colistin Polymyxin B
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§