Contents

Nafcillin

Chemical compound

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 Y
PubChem CID	8982
DrugBank	DB00607 Y
ChemSpider	8634 Y
UNII	SY07234TTS
ChEBI	CHEBI:7447 Y
ChEMBL	ChEMBL1443 Y
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 Y Key:GPXLMGHLHQJAGZ-JTDSTZFVSA-N Y
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Nafcillin sodium is a narrow-spectrum^[1] beta-lactam antibiotic^[2] of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, speciesofstaphylococci 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.^[3]

Indications[edit]

Nafcillin is indicated in the treatment of staphylococcal infections, except those caused by MRSA.^[4]

U.S. clinical practice guidelines recommend either nafcillin or oxacillin as the first-line treatment of choice for staphylococcal endocarditis in patients without artificial heart valves.^[5]

Side-effects[edit]

As with all penicillins, serious life-threatening allergic reactions can occur. ^{[citation needed]}

Milder side-effects include:

• Hypokalemia^[6]
• Nausea and vomiting
• Diarrhea, often due to suppression of normal gastrointestinal bacteria, which, on occasion, leads to a more serious super-infection with an organism like Clostridium difficile
• Abdominal pain
• Yeast infections (thrush) affecting the mouth and tongueorvagina
• Agranulocytosis, neutropenia

Interactions[edit]

There is evidence that nafcillin induces cytochrome P-450 enzymes, specifically CYP2C9. Several drugs with a narrow therapeutic window, such as warfarin and nifedipine, are metabolized by CYP2C9.^[7]

Nafcillin contains salts added as stability media. These added salts could cause edema or fluid accumulation. It would be prudent to avoid this medication if there were a concern for a congestive heart failure or kidney disease.^{[citation needed]}

References[edit]