U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of NAFCILLIN

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

HIDE SMILES / InChI

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
UNIPEN

Approved Use

Nafcillin 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 Date

1970
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
58 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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%)
Leukopenia (1%)
Hypernatremia (1%)
Hypersensitivity (3%)
Sources:
1 g single, oral
Highest studied dose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
healthy
n = 10
Health Status: healthy
Sex: M+F
Population Size: 10
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Haemophilus aphrophilus endocarditis after tongue piercing.
2002 Aug
Clinical failures of linezolid and implications for the clinical microbiology laboratory.
2002 Dec
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.
2002 Jul-Aug
Staphylococcus aureus meningitis: experience with cefuroxime treatment during a 16 year period in a Danish region.
2003
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
Evidence of an interaction between nifedipine and nafcillin in humans.
2003 Jun
Piperacillin induced bone marrow suppression: a case report.
2003 Jun 5
Metastatic intracranial abscesses of bronchopulmonary origin.
2003 Mar
Infective endocarditis and cardiac surgery in intravenous drug abusers and HIV-1 infected patients.
2003 May
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
Community-acquired methicillin-resistant Staphylococcus aureus prostatic abscess.
2004 Oct
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
Community-associated methicillin-resistant Staphylococcus aureus in pediatric patients.
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
Dermatoses of pregnancy update.
2005 May
Antibiotic treatment of osteomyelitis: what have we learned from 30 years of clinical trials?
2005 May
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
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
Pericardial tamponade masquerading as septic shock.
2007 Feb
Molecularly imprinted sol-gels for nafcillin determination in milk-based products.
2007 Feb 7
Analysis of different beta-lactams antibiotics in pharmaceutical preparations using micellar electrokinetic capillary chromatography.
2007 Jan 17
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
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
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
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
Predominant contribution of rat organic anion transporting polypeptide-2 (Oatp2) to hepatic uptake of beta-lactam antibiotics.
2008 Mar
Nafcillin-loaded PLGA nanoparticles for treatment of osteomyelitis.
2008 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
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 Sat Dec 16 17:51:45 GMT 2023
Edited
by admin
on Sat Dec 16 17:51:45 GMT 2023
Record UNII
4CNZ27M7RV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAFCILLIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NAFCILLIN [VANDF]
Common Name English
(2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-6-(((2-ETHOXY-L-NAPHTHALENYL)CARBONYL)-AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Common Name English
nafcillin [INN]
Common Name English
NAFCILLIN [MI]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2-ETHOXY-1-NAPHTHALENYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S,5R,6R)-
Common Name English
Nafcillin [WHO-DD]
Common Name English
NAFCILLIN [HSDB]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
WHO-VATC QJ01CF06
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
LIVERTOX NBK548403
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
WHO-ATC J01CF06
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000175497
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NDF-RT N0000011281
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
NCI_THESAURUS C260
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
205-690-9
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
WIKIPEDIA
NAFCILLIN
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
LACTMED
Nafcillin
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
MERCK INDEX
m7706
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY Merck Index
HSDB
3133
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
FDA UNII
4CNZ27M7RV
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
CAS
147-52-4
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL1443
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
EVMPD
SUB09118MIG
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
RXCUI
7233
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY RxNorm
SMS_ID
100000084431
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
DAILYMED
4CNZ27M7RV
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
CHEBI
7447
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023343
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
PUBCHEM
8982
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
DRUG BANK
DB00607
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
INN
1491
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
NCI_THESAURUS
C62053
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
MESH
D009254
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
DRUG CENTRAL
1869
Created by admin on Sat Dec 16 17:51:46 GMT 2023 , Edited by admin on Sat Dec 16 17:51:46 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Population
PHARMACOKINETIC
Population
PHARMACOKINETIC
Population
PHARMACOKINETIC
Population
PHARMACOKINETIC