Dicloxacillin

Dicloxacillin

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a685017
Pregnancy category	AU: B2 US: B (No risk in non-human studies)
Routes of administration	Oral
ATC code	J01CF01 (WHO) QJ51CF01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60 to 80%
Protein binding	98%
Metabolism	Hepatic
Biological half-life	0.7 hours
Excretion	Renal and biliary
Identifiers
IUPAC name (2S,5R,6R)-6-{[3-(2,6-dichlorophenyl)-5-methyl- oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia- 1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number	3116-76-5 Y
PubChem CID	18381
DrugBank	DB00485 Y
ChemSpider	17358 Y
UNII	COF19H7WBK
KEGG	D02348 Y
ChEBI	CHEBI:4511 Y
ChEMBL	CHEMBL893 Y
ECHA InfoCard	100.019.535
Chemical and physical data
Formula	C19H17Cl2N3O5S
Molar mass	470.327 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1c(Cl)cccc1Cl)C)[C@H]4SC3(C)C
InChI InChI=1S/C19H17Cl2N3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1 Y Key:YFAGHNZHGGCZAX-JKIFEVAISA-N Y

Dicloxacillin is a narrow-spectrum β-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).

Dicloxacillin is used to treat mild-to-moderate staphylococcal infections. To decrease the development of resistance, dicloxacillin is recommended to treat infections that are suspected or proven to be caused by beta-lactamase-producing bacteria.

Dicloxacillin is similar in pharmacokinetics, antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable. It is believed to have lower incidence of severe hepatic adverse effects than flucloxacillin, but a higher incidence of renal adverse effects.

Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:

Dicloxacillin is commercially available as the sodium salt, dicloxacillin sodium, in capsules and as a powder for reconstitution.

Dicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/anaphylactic reaction) to any penicillins.

Common adverse drug reactions (ADRs) associated with the use of dicloxacillin include: diarrhoea, nausea, rash, urticaria, pain and inflammation at injection site, superinfection (including candidiasis), allergy, and transient increases in liver enzymes and bilirubin.