Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H22N2O5S.C16H20N2 |
| Molecular Weight | 654.818 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)C5=C(OCC)C=CC6=CC=CC=C56)C(O)=O
InChI
InChIKey=HYJHTTQKOSMGMX-FRFVDRIFSA-N
InChI=1S/C21H22N2O5S.C16H20N2/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;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);1-10,17-18H,11-14H2/t15-,16+,19-;/m1./s1
| Molecular Formula | C16H20N2 |
| Molecular Weight | 240.3434 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C21H22N2O5S |
| Molecular Weight | 414.475 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2362972 |
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 Date1970 |
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 |
|---|---|---|---|---|
Page: 6.0 |
likely | |||
| major | ||||
| moderate |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Continuous antibiotic prophylaxis and cerebral spinal fluid infection in patients with intracranial pressure monitors. | 2004 |
|
| Pseudomonas aeruginosa, Staphylococcus aureus, and fluoroquinolone use. | 2005 Aug |
|
| High-throughput analysis of tetracycline and penicillin antibiotics in animal tissues using electrospray tandem mass spectrometry with selected reaction monitoring transition. | 2005 Dec 30 |
|
| 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 |
|
| Antibiotic dosing in critically ill adult patients receiving continuous renal replacement therapy. | 2005 Oct 15 |
|
| Pharmaceutical liquid crystals: the relevance of partially ordered systems. | 2005 Sep |
|
| Tricuspid valve endocarditis with Group B Streptococcus after an elective abortion: the need for new data. | 2006 |
|
| Staphylococcal septic synovitis of the sternoclavicular joint with retrosternal extension. | 2006 Aug |
|
| Rapid identification of P-glycoprotein substrates and inhibitors. | 2006 Dec |
|
| The role of vancomycin in the treatment paradigm. | 2006 Jan 1 |
|
| 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 |
|
| Molecular imprinted ormosils for nafcillin recognition by room temperature phosphorescence optosensing. | 2006 Mar 15 |
|
| Invasive nontypeable Haemophilus influenzae infection in an adult with laryngeal cancer. | 2006 May |
|
| A framework toward restoration of writing order from single-stroked handwriting image. | 2006 Nov |
|
| In vitro activity effects of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant Staphylococcus spp. strains. | 2006 Oct 12 |
|
| 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 |
|
| Four cases of nafcillin-associated acute interstitial nephritis in one institution. | 2007 Aug |
|
| Necrotizing fasciitis: strategies for diagnosis and management. | 2007 Aug 7 |
|
| Pericardial tamponade masquerading as septic shock. | 2007 Feb |
|
| Molecularly imprinted sol-gels for nafcillin determination in milk-based products. | 2007 Feb 7 |
|
| Sure signs. | 2007 Jan |
|
| Direct extraction of penicillin G and derivatives from aqueous samples using a stoichiometrically imprinted polymer. | 2007 Jan 15 |
|
| Impact of antibiotics on expression of virulence-associated exotoxin genes in methicillin-sensitive and methicillin-resistant Staphylococcus aureus. | 2007 Jan 15 |
|
| Analysis of different beta-lactams antibiotics in pharmaceutical preparations using micellar electrokinetic capillary chromatography. | 2007 Jan 17 |
|
| Stable competitive enzyme-linked immunosorbent assay kit for rapid measurement of 11 active beta-lactams in milk, tissue, urine, and serum. | 2007 Jan-Feb |
|
| Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays. | 2007 Jul 1 |
|
| 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 |
|
| Large-volume sample stacking for the analysis of seven beta-lactam antibiotics in milk samples of different origins by CZE. | 2007 Nov |
|
| Treatment of acute salmonella epiphyseal osteomyelitis using computed tomography-guided drainage in a child without sickle cell disease. | 2007 Nov |
|
| 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 |
|
| Paraspinal abscess complicated by endocarditis following a facet joint injection. | 2008 Apr |
|
| A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. | 2008 Aug |
|
| Streamlining methodology for the multiresidue analysis of beta-lactam antibiotics in bovine kidney using liquid chromatography-tandem mass spectrometry. | 2008 Aug 22 |
|
| The AraC-family regulator GadX enhances multidrug resistance in Escherichia coli by activating expression of mdtEF multidrug efflux genes. | 2008 Feb |
|
| Role of surface adsorption and porosity features in the molecular recognition ability of imprinted sol-gels. | 2008 Feb 28 |
|
| 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 |
|
| A prickly situation. | 2008 Mar |
|
| Predominant contribution of rat organic anion transporting polypeptide-2 (Oatp2) to hepatic uptake of beta-lactam antibiotics. | 2008 Mar |
|
| 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 |
|
| Case report: diabetic myonecrosis of the neck complicated by infection in an islet transplanted patient. | 2009 Mar-Apr |
Patents
Sample Use Guides
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
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:25:35 GMT 2023
by
admin
on
Fri Dec 15 18:25:35 GMT 2023
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| Record UNII |
OOG512995N
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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Common Name | English | ||
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Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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23288-39-3
Created by
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OOG512995N
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71300361
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