Nafcillin

Nafcillin

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
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a685019
Pregnancy cat.	B(US)
Legal status	℞ Prescription only
Routes	IM, IV
Pharmacokinetic data
Protein binding	90%
Metabolism	<30% hepatic
Half-life	0.5 hours
Excretion	Biliary and renal
Identifiers
CAS number	985-16-0 Y
ATC code	None
PubChem	CID 8982
DrugBank	APRD01130
ChemSpider	8634 Y
UNII	SY07234TTS Y
ChEBI	CHEBI:7447 N
ChEMBL	CHEMBL1443 Y
Chemical data
Formula	C21H22N2O5S
Mol. mass	414.476 g/mol
SMILES	eMolecules & PubChem
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
N(what is this?)  (verify)

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, species of staphylococci that are resistant to other penicillins.

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

Indications

Nafcillin is 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:

• 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 tongue or vagina
• Agranulocytosis, neutropenia

Interactions

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 accumulation. It would be prudent to avoid this medication if there were a concern for a congestive heart failure or kidney disease.

References

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. http://linkinghub.elsevier.com/retrieve/pii/0003-4975(94)00992-9. 
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. PMC 1130660. PMID 1731755. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1130660. 
3. ^ ^{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.
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. doi:10.1046/j.1365-2125.2003.01789.x. PMC 1884262. PMID 12814453. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0306-5251&date=2003&volume=55&issue=6&spage=588.