Nafcillin
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Nafcillin
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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 | |
| Identifiers | |
| CAS number | |
| ATC code | none |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C21H22N2O5S |
| Mol. mass | 414.476 g/mol |
| SMILES | & |
| 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 |
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]
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[edit] Indications
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]
[edit] Side effects
As with all penicillins, serious life-threatening allergic reactions can occur.
Milder side effects include:
- Nausea and vomiting
- Diarrhea, often due to suppression of normal gastrointestinal bacteria. Occasionally, this leads to a more serious super-infection with an organism like Clostridium difficile
- Abdominal pain
- Yeast infections (thrush) affecting the mouth and tongue or vagina
[edit] Interactions
There is evidence that it induces cytochrome P-450 enzymes.[5]
[edit] References
- ^ 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:. PMID 7887701. http://linkinghub.elsevier.com/retrieve/pii/0003-4975(94)00992-9.
- ^ 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.
- ^ a b Pham P, Bartlett JG (January 2, 2009). "Nafcillin". Point-of-Care Information Technology ABX Guide. Johns Hopkins University. http://prod.hopkins-abxguide.org/antibiotics/antibacterial/penicillinase-resistant_pcn/nafcillin.html. Retrieved on July 10, 2009. Freely available with registration.
- ^ 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:. PMID 16880336.
- ^ 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. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0306-5251&date=2003&volume=55&issue=6&spage=588.
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