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Nafcillin

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Nafcillin
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa685019
Routes of
administration
IM,IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding90%
Metabolism<30%hepatic
Eliminationhalf-life0.5 hours
ExcretionBiliary andrenal
Identifiers
  • (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
PubChemCID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.005.174Edit this at Wikidata
Chemical and physical data
FormulaC21H22N2O5S
Molar mass414.48 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 checkY
  • Key:GPXLMGHLHQJAGZ-JTDSTZFVSA-N checkY
  (verify)

Nafcillin sodium is anarrow-spectrum,[1] second-generationbeta-lactam antibiotic[2] of thepenicillin class. As abeta-lactamase-resistant penicillin, it is used to treatinfections caused byGram-positive bacteria, in particular,species ofstaphylococci that areresistant to other penicillins.

Nafcillin is considered therapeutically equivalent tooxacillin, although one retrospective study found greater rates ofhypokalemia andacute kidney injury in patients taking nafcillin compared to patients taking oxacillin.[3]

Indications

[edit]

Nafcillin is indicated in the treatment ofstaphylococcal infections, except those caused byMRSA.[4]

U.S.clinical practice guidelines recommend either nafcillin or oxacillin as thefirst-line treatment of choice for staphylococcalendocarditis in patients withoutartificial heart valves.[5]

Side-effects

[edit]

As with all penicillins, serious life-threateningallergic reactions can occur.[citation needed]

Milder side-effects include:

Interactions

[edit]

There is evidence that nafcillin inducescytochrome P-450 enzymes, specificallyCYP2C9. Several drugs with a narrowtherapeutic window, such as warfarin and nifedipine, are metabolized by CYP2C9.[7]

Nafcillin contains salts added as stability media. These added salts could causeedema 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]
  1. ^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.
  2. ^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.
  3. ^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.
  4. ^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.
  5. ^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.
  6. ^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.
  7. ^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.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems /Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking:Ramoplanin§
Intracellular
Other
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
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