Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H22N2O5S |
Molecular Weight | 414.475 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(OCC)C=CC4=CC=CC=C34)C(O)=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 |
|
Isolated septic arthritis caused by penicillin-resistant Streptococcus pneumoniae. | 2001 Apr |
|
Comparative evaluation of oral levofloxacin and parenteral nafcillin in the treatment of experimental methicillin-susceptible Staphylococcus aureus osteomyelitis in rabbits. | 2001 Aug |
|
Adsorption of an amphiphilic penicillin onto human serum albumin: characterisation of the complex. | 2001 Aug 30 |
|
Antimicrobial resistance: steps to reduce the problem with emphasis on antibiotic utilization the Rapid City experience. | 2001 Feb |
|
Possible role of cellular immunity: a case of cellulitis. | 2001 Jan |
|
Solid-phase extraction followed by liquid chromatography-mass spectrometry for trace determination of beta-lactam antibiotics in bovine milk. | 2001 Jul |
|
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | 2001 Sep-Oct |
|
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay. | 2002 |
|
Effect of UV-B radiation on some common antibiotics. | 2002 Apr |
|
Haemophilus aphrophilus endocarditis after tongue piercing. | 2002 Aug |
|
Shorter courses of parenteral antibiotic therapy do not appear to influence response rates for children with acute hematogenous osteomyelitis: a systematic review. | 2002 Aug 14 |
|
Clinical failures of linezolid and implications for the clinical microbiology laboratory. | 2002 Dec |
|
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 |
|
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study. | 2002 Jul-Aug |
|
Infective endocarditis in intravenous drug abusers and HIV-1 infected patients. | 2002 Jun |
|
Evaluation of UV-radiation induced singlet oxygen generation potential of selected drugs. | 2002 May |
|
Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan. | 2002 Nov |
|
Clindamycin for intraincisional antibiotic prophylaxis in dermatologic surgery. | 2002 Sep |
|
Case study: submandibular mass in a premature infant. | 2003 Apr |
|
Synthesis and screening of a molecularly imprinted polymer library targeted for penicillin G. | 2003 Jan-Feb |
|
28-year-old man with recurrent fever. | 2003 Jul |
|
Effect of disruption of Staphylococcus aureus PBP4 gene on resistance to beta-lactam antibiotics. | 2003 Winter |
|
Endophthalmitis after penetrating keratoplasty: microbiologic spectrum and susceptibility of isolates. | 2004 Feb |
|
Major structural differences and novel potential virulence mechanisms from the genomes of multiple campylobacter species. | 2005 Jan |
|
Evaluation of the efficacy and safety of outpatient parenteral antimicrobial therapy for infections with methicillin-sensitive Staphylococcus aureus. | 2005 Jun |
|
An unusual Gram stain finding. | 2005 Jun 1 |
|
Chronic Staphylococcus aureus infection leading to pyogenic granuloma and preventing socket re-epithelialization after orbital exenteration. | 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 |
|
Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays. | 2006 Mar 15 |
|
Bacteremia and endocarditis due to methicillin-resistant Staphylococcus aureus: the potential role of daptomycin. | 2007 Aug |
|
Sure signs. | 2007 Jan |
|
Impact of antibiotics on expression of virulence-associated exotoxin genes in methicillin-sensitive and methicillin-resistant Staphylococcus aureus. | 2007 Jan 15 |
|
Streptobacillus moniliformis septic arthritis: a clinical entity distinct from rat-bite fever? | 2007 Jun 11 |
|
[Sensitivity to various antibiotics of coagulase-negative staphylococci isolated from samples of milk from Dutch dairy cattle]. | 2007 Mar 15 |
|
Interaction between warfarin and nafcillin: case report and review of the literature. | 2007 Oct |
|
An overview of harms associated with beta-lactam antimicrobials: where do the carbapenems fit in? | 2008 |
|
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. | 2008 Aug |
|
The AraC-family regulator GadX enhances multidrug resistance in Escherichia coli by activating expression of mdtEF multidrug efflux genes. | 2008 Feb |
|
Variability in vancomycin use in newborn intensive care units determined from data in an electronic medical record. | 2008 Jul |
|
Trace determination of beta-lactam antibiotics in environmental aqueous samples using off-line and on-line preconcentration in capillary electrophoresis. | 2008 Mar 28 |
|
Nafcillin-loaded PLGA nanoparticles for treatment of osteomyelitis. | 2008 Sep |
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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N0000011281
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N0000011281
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N0000011281
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N0000011281
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QJ01CF06
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LIVERTOX |
NBK548403
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WHO-ATC |
J01CF06
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NDF-RT |
N0000011281
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N0000175497
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N0000011281
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N0000011281
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N0000011281
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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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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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4CNZ27M7RV
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7447
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C62053
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D009254
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1869
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ACTIVE MOIETY