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

Description

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

1964
104
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8146
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8307
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

8.2944E9
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
18.06 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050655s017lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050655s017lbl.pdf
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

Funbound

ValueDoseCo-administeredAnalytePopulation
10.1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050655s017lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
Disc. AE: Acute kidney injury...
AEs leading to
discontinuation/dose reduction:
Acute kidney injury (15%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26976858
12 g single, intravenous|intramuscular
Dose: 12 g
Route: intravenous|intramuscular
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26976858
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
Disc. AE: Hypokalemia, Leukopenia...
AEs leading to
discontinuation/dose reduction:
Hypokalemia (15%)
Leukopenia (1%)
Hypernatremia (1%)
Hypersensitivity (3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26976858
1 g single, oral
Highest studied dose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/879745
healthy
n = 10
Health Status: healthy
Sex: M+F
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/879745
Sources:
https://pubmed.ncbi.nlm.nih.gov/879745
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
Hypernatremia 1%
Disc. AE
12 g single, intravenous|intramuscular
Dose: 12 g
Route: intravenous|intramuscular
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26976858
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
Leukopenia 1%
Disc. AE
12 g single, intravenous|intramuscular
Dose: 12 g
Route: intravenous|intramuscular
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26976858
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
Hypokalemia 15%
Disc. AE
12 g single, intravenous|intramuscular
Dose: 12 g
Route: intravenous|intramuscular
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26976858
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
Hypersensitivity 3%
Disc. AE
12 g single, intravenous|intramuscular
Dose: 12 g
Route: intravenous|intramuscular
Route: single
Dose: 12 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26976858
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:
https://pubmed.ncbi.nlm.nih.gov/26976858
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
753

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1491

OATP1B3
333

OATP1B1
389
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1857
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1491
 likely
OATP1B3
333
 major
OATP1B1
389
 moderate
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7447
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7447
ChemicalBook
CB9914919
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9914919
ZINC
ZINC000003875980
http://zinc15.docking.org/substances/ZINC000003875980
PubMed

PubMed

TitleDatePubMed
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

Patents

JP2009541210A
78

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
In Vitro Use Guide
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.
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 Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
WHO-VATC QJ01CF06
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
LIVERTOX NBK548403
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
WHO-ATC J01CF06
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000175497
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NDF-RT N0000011281
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
NCI_THESAURUS C260
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
Code System Code Type Description
ECHA (EC/EINECS)
205-690-9
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
WIKIPEDIA
NAFCILLIN
Created by admin on Sun Dec 18 20:57:49 UTC 2022 , Edited by admin on Sun Dec 18 20:57:49 UTC 2022
PRIMARY
LACTMED
Nafcillin
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
MERCK INDEX
M7706
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY Merck Index
HSDB
3133
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
FDA UNII
4CNZ27M7RV
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
CAS
147-52-4
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
ChEMBL
CHEMBL1443
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
EVMPD
SUB09118MIG
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
RXCUI
7233
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY RxNorm
DAILYMED
4CNZ27M7RV
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
CHEBI
7447
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
EPA CompTox
DTXSID8023343
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
PUBCHEM
8982
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
DRUG BANK
DB00607
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
INN
1491
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
NCI_THESAURUS
C62053
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
MESH
D009254
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
DRUG CENTRAL
1869
Created by admin on Sun Dec 18 20:57:48 UTC 2022 , Edited by admin on Sun Dec 18 20:57:48 UTC 2022
PRIMARY
ACTIVE MOIETY
Structure of NAFCILLIN
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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