Nafcillin

Nafcillin
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a685019
Routes of; administration	IM, IV
ATC code	J01CF06 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	90%
Metabolism	<30% hepatic
Elimination half-life	0.5 hours
Excretion	Biliary and renal
Identifiers
	IUPAC name (2S,5R,6R)-6-[(2-ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	985-16-0 ;
PubChem CID	8982;
DrugBank	DB00607 ;
ChemSpider	8634 ;
UNII	SY07234TTS;
ChEBI	CHEBI:7447 ;
ChEMBL	ChEMBL1443 ;
CompTox Dashboard (EPA)	DTXSID8023343 ;
ECHA InfoCard	100.005.174
Chemical and physical data
Formula	C21H22N2O5S
Molar mass	414.48 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c1ccccc1ccc2OCC)[C@H]4SC3(C)C;
	InChI InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1 ; Key:GPXLMGHLHQJAGZ-JTDSTZFVSA-N ;
	(verify)

Nafcillin sodium is a narrow-spectrum, second-generation beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.

Nafcillin is considered therapeutically equivalent to oxacillin, although one retrospective study found greater rates of hypokalemia and acute kidney injury in patients taking nafcillin compared to patients taking oxacillin.