Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H22N2O5S |
Molecular Weight | 414.4767 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOc1ccc2ccccc2c1C(=N[C@]3([H])C(=O)N4[C@@]([H])(C(=O)O)C(C)(C)S[C@]34[H])O
InChI
InChIKey=GPXLMGHLHQJAGZ-JTDSTZFVSA-N
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
DescriptionSources: https://www.drugs.com/pro/nafcillin.html
Sources: https://www.drugs.com/pro/nafcillin.html
Nafcillin is a beta-lactam antibiotic of 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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2362972 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | UNIPEN Approved UseNafcillin for injection, USP is indicated in the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug. Culture and susceptibility tests should be performed initially to determine the causative organism and its susceptibility to the drug. Nafcillin for injection, USP may be used to initiate therapy in suspected cases of resistant staphylococcal infections prior to the availability of susceptibility test results. Nafcillin for injection, USP should not be used in infections caused by organisms susceptible to penicillin G. If the susceptibility tests indicate that the infection is due to an organism other than a resistant Staphylococcus, therapy should not be continued with nafcillin for injection, USP. To reduce the development of drug-resistant bacteria and maintain the effectiveness of nafcillin for injection, USP and other antibacterial drugs, nafcillin for injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date8.2944E9 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
58 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2311446 |
50 mg/kg 4 times / day multiple, intravenous dose: 50 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
NAFCILLIN serum | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.06 μg × h/mL |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NAFCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
47 min |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NAFCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
31 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2311446 |
50 mg/kg 4 times / day multiple, intravenous dose: 50 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
NAFCILLIN serum | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.1% |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NAFCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
12 g single, intravenous|intramuscular Highest studied dose Dose: 12 g Route: intravenous|intramuscular Route: single Dose: 12 g Sources: |
unhealthy|healthy, 54 years (range: 19–90 years) n = 160 Health Status: unhealthy|healthy Age Group: 54 years (range: 19–90 years) Sex: M+F Population Size: 160 Sources: |
Disc. AE: Acute kidney injury... AEs leading to discontinuation/dose reduction: Acute kidney injury (15%) Sources: |
12 g single, intravenous|intramuscular Dose: 12 g Route: intravenous|intramuscular Route: single Dose: 12 g Sources: |
unhealthy|healthy, 54 years (range: 19–90 years) n = 160 Health Status: unhealthy|healthy Age Group: 54 years (range: 19–90 years) Sex: M+F Population Size: 160 Sources: |
Disc. AE: Hypokalemia, Leukopenia... AEs leading to discontinuation/dose reduction: Hypokalemia (15%) Sources: Leukopenia (1%) Hypernatremia (1%) Hypersensitivity (3%) |
1 g single, oral Highest studied dose |
healthy n = 10 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Acute kidney injury | 15% Disc. AE |
12 g single, intravenous|intramuscular Highest studied dose Dose: 12 g Route: intravenous|intramuscular Route: single Dose: 12 g Sources: |
unhealthy|healthy, 54 years (range: 19–90 years) n = 160 Health Status: unhealthy|healthy Age Group: 54 years (range: 19–90 years) Sex: M+F Population Size: 160 Sources: |
Hypernatremia | 1% Disc. AE |
12 g single, intravenous|intramuscular Dose: 12 g Route: intravenous|intramuscular Route: single Dose: 12 g Sources: |
unhealthy|healthy, 54 years (range: 19–90 years) n = 160 Health Status: unhealthy|healthy Age Group: 54 years (range: 19–90 years) Sex: M+F Population Size: 160 Sources: |
Leukopenia | 1% Disc. AE |
12 g single, intravenous|intramuscular Dose: 12 g Route: intravenous|intramuscular Route: single Dose: 12 g Sources: |
unhealthy|healthy, 54 years (range: 19–90 years) n = 160 Health Status: unhealthy|healthy Age Group: 54 years (range: 19–90 years) Sex: M+F Population Size: 160 Sources: |
Hypokalemia | 15% Disc. AE |
12 g single, intravenous|intramuscular Dose: 12 g Route: intravenous|intramuscular Route: single Dose: 12 g Sources: |
unhealthy|healthy, 54 years (range: 19–90 years) n = 160 Health Status: unhealthy|healthy Age Group: 54 years (range: 19–90 years) Sex: M+F Population Size: 160 Sources: |
Hypersensitivity | 3% Disc. AE |
12 g single, intravenous|intramuscular Dose: 12 g Route: intravenous|intramuscular Route: single Dose: 12 g Sources: |
unhealthy|healthy, 54 years (range: 19–90 years) n = 160 Health Status: unhealthy|healthy Age Group: 54 years (range: 19–90 years) Sex: M+F Population Size: 160 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/ Page: 6.0 |
likely | |||
major | ||||
moderate |
PubMed
Title | Date | PubMed |
---|---|---|
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children. | 2001 |
|
Optimisation of the prevention and treatment of bacterial endocarditis. | 2001 |
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Antimicrobial resistance: steps to reduce the problem with emphasis on antibiotic utilization the Rapid City experience. | 2001 Feb |
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Solid-phase extraction followed by liquid chromatography-mass spectrometry for trace determination of beta-lactam antibiotics in bovine milk. | 2001 Jul |
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Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin, nafcillin and dicloxacillin, in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry. | 2001 Mar 16 |
|
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay. | 2002 |
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Effect of UV-B radiation on some common antibiotics. | 2002 Apr |
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Higher occurrence of hepatotoxicity and rash in patients treated with oxacillin, compared with those treated with nafcillin and other commonly used antimicrobials. | 2002 Jan 1 |
|
Delayed intracranial migration of cervical sublaminar and interspinous wires and subsequent cerebellar abscess. Case report. | 2002 Jul |
|
Clindamycin for intraincisional antibiotic prophylaxis in dermatologic surgery. | 2002 Sep |
|
Staphylococcus aureus meningitis: experience with cefuroxime treatment during a 16 year period in a Danish region. | 2003 |
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Clindamycin treatment of invasive infections caused by community-acquired, methicillin-resistant and methicillin-susceptible Staphylococcus aureus in children. | 2003 Jul |
|
28-year-old man with recurrent fever. | 2003 Jul |
|
Evidence of an interaction between nifedipine and nafcillin in humans. | 2003 Jun |
|
Piperacillin induced bone marrow suppression: a case report. | 2003 Jun 5 |
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Staphylococcus aureus bacteremia: recurrence and the impact of antibiotic treatment in a prospective multicenter study. | 2003 Sep |
|
Assessment of molecularly imprinted sol-gel materials for selective room temperature phosphorescence recognition of nafcillin. | 2004 May 5 |
|
Influence of temperature and drug concentration on nafcillin precipitation. | 2005 Jul 1 |
|
Evaluation of the efficacy and safety of outpatient parenteral antimicrobial therapy for infections with methicillin-sensitive Staphylococcus aureus. | 2005 Jun |
|
Dermatoses of pregnancy update. | 2005 May |
|
Embolic stroke complicating Staphylococcus aureus endocarditis circumstantially linked to rectal trauma from foreign body: a first case report. | 2005 May 27 |
|
Pharmaceutical liquid crystals: the relevance of partially ordered systems. | 2005 Sep |
|
Staphylococcal septic synovitis of the sternoclavicular joint with retrosternal extension. | 2006 Aug |
|
Rapid identification of P-glycoprotein substrates and inhibitors. | 2006 Dec |
|
A review of daptomycin for injection (Cubicin) in the treatment of complicated skin and skin structure infections. | 2006 Jun |
|
A passage to injury. | 2006 Jun |
|
In vitro evaluation of the antibiotic lock technique (ALT) for the treatment of catheter-related infections caused by staphylococci. | 2006 Jun |
|
Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays. | 2006 Mar 15 |
|
A framework toward restoration of writing order from single-stroked handwriting image. | 2006 Nov |
|
Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry. | 2006 Oct 13 |
|
Bacteremia and endocarditis due to methicillin-resistant Staphylococcus aureus: the potential role of daptomycin. | 2007 Aug |
|
Pericardial tamponade masquerading as septic shock. | 2007 Feb |
|
Direct extraction of penicillin G and derivatives from aqueous samples using a stoichiometrically imprinted polymer. | 2007 Jan 15 |
|
Streptobacillus moniliformis septic arthritis: a clinical entity distinct from rat-bite fever? | 2007 Jun 11 |
|
Treatment of acute salmonella epiphyseal osteomyelitis using computed tomography-guided drainage in a child without sickle cell disease. | 2007 Nov |
|
An overview of harms associated with beta-lactam antimicrobials: where do the carbapenems fit in? | 2008 |
|
Paraspinal abscess complicated by endocarditis following a facet joint injection. | 2008 Apr |
|
Efficacy of telavancin in a murine model of pneumonia induced by methicillin-susceptible Staphylococcus aureus. | 2008 Jan |
|
Variability in vancomycin use in newborn intensive care units determined from data in an electronic medical record. | 2008 Jul |
|
Comprehensive screening and quantification of veterinary drugs in milk using UPLC-ToF-MS. | 2008 Jul |
|
Case report: diabetic myonecrosis of the neck complicated by infection in an islet transplanted patient. | 2009 Mar-Apr |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/nafcillin.html
Nafcillin for Injection ADD-Vantage® Vial is to be administered intravenously. The usual I.V. dosage for adults is 500 mg every 4 hours. For severe infections, 1 gram every 4 hours is recommended. Administer slowly over at least 30 to 60 minutes to minimize the risk of vein irritation and extravasation. Bacteriologic studies to determine the causative organisms and their susceptibility to Nafcillin should always be performed. Duration of therapy varies with the type and severity of infection as well as the overall condition of the patient; therefore, it should be determined by the clinical and bacteriological response of the patient. In severe staphylococcal infections, therapy with Nafcillin should be continued for at least 14 days. Therapy should be continued for at least 48 hours after the patient has become afebrile, asymptomatic, and cultures are negative. The treatment of endocarditis and osteomyelitis may require a longer duration of therapy.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18725435
MICs and minimum bactericidal concentrations (MBCs) were determined for in triplicate by microdilution techniques using an inoculum of 5 × 105 CFU/ml according to Clinical and Laboratory Standards Institute guidelines. For MBC determinations, aliquots (5 μl) from clear wells were plated onto tryptic soy agar drug-free plates followed by incubation at 37°C for 24 and 48 h. MIC data were reported as median values from at least three independent experiments for each antibiotic. MIC for nafcillin-sensitive S.aureli strains was determined to be 1 ug/ml.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000011281
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N0000011281
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N0000011281
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N0000011281
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WHO-VATC |
QJ01CF06
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LIVERTOX |
661
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WHO-ATC |
J01CF06
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NDF-RT |
N0000011281
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NDF-RT |
N0000175497
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NCI_THESAURUS |
C260
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205-690-9
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NAFCILLIN
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Nafcillin
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M7706
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PRIMARY | Merck Index | ||
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3133
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4CNZ27M7RV
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147-52-4
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CHEMBL1443
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SUB09118MIG
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7233
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147-52-4
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8982
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DB00607
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1491
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C62053
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D009254
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1869
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ACTIVE MOIETY