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Chemical compound
Nafcillin
AHFS /
Drugs.com
Monograph
MedlinePlus
a685019
Routes of administration
IM ,
IV
ATC code
Legal status
In general: ℞ (Prescription only)
Protein binding 90%
Metabolism <30%
hepatic
Elimination half-life 0.5 hours
Excretion Biliary and
renal
(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
PubChem
CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.005.174
Formula C 21 H 22 N 2 O 5 S
Molar mass 414.48 g·mol−1 3D model (
JSmol )
O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c1ccccc1ccc2OCC)[C@H]4SC3(C)C
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
(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 one retrospective study found greater rates of
hypokalemia and
acute kidney injury in patients taking nafcillin compared to patients taking oxacillin.
[3]
Indications
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
As with all penicillins, serious life-threatening
allergic reactions can occur. [
citation needed ]
Milder side-effects include:
Interactions
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
^ Palmer DL, Pett SB, Akl BF (March 1995).
"Bacterial wound colonization after broad-spectrum versus narrow-spectrum antibiotics" . The Annals of Thoracic Surgery . 59 (3): 626–631.
doi :
10.1016/0003-4975(94)00992-9 .
PMID
7887701 .
^ Tan AK, Fink AL (January 1992).
"Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase" . The Biochemical Journal . 281 (Pt 1): 191–196.
doi :
10.1042/bj2810191 .
PMC
1130660 .
PMID
1731755 .
^ Viehman JA, Oleksiuk LM, Sheridan KR, Byers KE, He P, Falcione BA, Shields RK (May 2016).
"Adverse Events Lead to Drug Discontinuation More Commonly among Patients Who Receive Nafcillin than among Those Who Receive Oxacillin" . Antimicrobial Agents and Chemotherapy . 60 (5): 3090–3095.
doi :
10.1128/AAC.03122-15 .
PMC
4862451 .
PMID
26976858 .
^ 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.
^ Bonow RO, Carabello BA, Kanu C, de Leon AC, Faxon DP, Freed MD, 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 .
^ Mohr JA, Clark RM, Waack TC, Whang R (August 1979). "Nafcillin-associated hypokalemia". JAMA . 242 (6): 544.
doi :
10.1001/jama.1979.03300060046028 .
PMID
448989 .
^ Lang CC, Jamal SK, Mohamed Z, Mustafa MR, Mustafa AM, Lee TC (June 2003).
"Evidence of an interaction between nifedipine and nafcillin in humans" . British Journal of Clinical Pharmacology . 55 (6): 588–590.
doi :
10.1046/j.1365-2125.2003.01789.x .
PMC
1884262 .
PMID
12814453 .
CAR Tooltip Constitutive androstane receptor
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