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Nafcillin: Wikis


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Systematic (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
ATC code none
PubChem 8982
DrugBank APRD01130
Chemical data
Formula C 21H22N2O5S 
Mol. mass 414.476 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Protein binding 90%
Metabolism <30% hepatic
Half life 0.5 hours
Excretion Biliary and renal
Therapeutic considerations
Pregnancy cat. B(US)
Legal status Prescription only
Routes IM, IV
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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, particularly species of staphylococci, that are resistant to other penicillins.

Nafcillin is considered therapeutically equivalent to oxacillin, although its safety profile is somewhat different.[3]



Nafcillin is particularly indicated in the treatment of staphylococcal infections, except those caused by MRSA.[3]

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.[4]

Side effects

As with all penicillins, serious life-threatening allergic reactions can occur.

Milder side effects include:


There is evidence that it induces cytochrome P-450 enzymes.[5]

The other aspect of this medication is that this medication contains lots of salts as media. So it could cause some edema or fluid accummulation. It would be prudent to avoid this medication if there was a concern for a congestive heart failure or kidney disease.


  1. ^ Palmer DL, Pett SB, Akl BF (March 1995). "Bacterial wound colonization after broad-spectrum versus narrow-spectrum antibiotics". Ann. Thorac. Surg. 59 (3): 626–31. doi:10.1016/0003-4975(94)00992-9. PMID 7887701.  
  2. ^ Tan AK, Fink AL (January 1992). "Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase". Biochem. J. 281 (Pt 1): 191–6. PMID 1731755.  
  3. ^ a b Pham P, Bartlett JG (January 2, 2009). "Nafcillin". Point-of-Care Information Technology ABX Guide. Johns Hopkins University.   Retrieved on July 10, 2009. Freely available with registration.
  4. ^ Bonow RO, Carabello BA, Kanu C, et al. (August 2006). "ACC/AHA 2006 guidelines for the management of patients with valvular heart disease: a report of the American College of Cardiology/American Heart Association Task Force on Practice Guidelines (writing committee to revise the 1998 Guidelines for the Management of Patients With Valvular Heart Disease): developed in collaboration with the Society of Cardiovascular Anesthesiologists: endorsed by the Society for Cardiovascular Angiography and Interventions and the Society of Thoracic Surgeons". Circulation 114 (5): e84–231. doi:10.1161/CIRCULATIONAHA.106.176857. PMID 16880336.  
  5. ^ Lang CC, Jamal SK, Mohamed Z, Mustafa MR, Mustafa AM, Lee TC (June 2003). "Evidence of an interaction between nifedipine and nafcillin in humans". Br J Clin Pharmacol 55 (6): 588–90. PMID 12814453. PMC 1884262.  

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