Identification

Name
Nafcillin
Accession Number
DB00607  (APRD01130, DB08269)
Type
Small Molecule
Groups
Approved, Investigational
Description

A semi-synthetic antibiotic related to penicillin, Naficillin is a narrow-spectrum beta-lactam antibiotic drug. It is a beta-lactamase-resistant penicillin that is indicated for the treatment of Staphylococcal infections caused by strains that are resistant to other penicillins, except those caused by MRSA. It may be used as a first-line therapy in Methicillin-Sensitive Staphylococcus aureus infections [1].

Structure
Thumb
Synonyms
  • (2-Ethoxy-1-naphthalenyl)penicillin
  • (2-Ethoxy-1-naphthyl)penicillin
  • (2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 6-(2-Ethoxy-1-naphthamido)penicillanic acid
  • Nafcilina
  • Nafcilline
  • Nafcillinum
  • Naphcillin
Product Ingredients
IngredientUNIICASInChI Key
Nafcillin SodiumSY07234TTS985-16-0AYAPZOUDXCDGIF-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NafcillinInjection, solution2 g/100mLIntravenousBaxter Laboratories1989-10-31Not applicableUs
NafcillinInjection, solution1 g/50mLIntravenousBaxter Laboratories1989-10-31Not applicableUs
Unipen Injection Pws 500mg/vialPowder, for solution500 mgIntramuscular; IntravenousWyeth Ayerst Canada Inc.1994-12-311998-08-13Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NafcillinInjection, powder, for solution10 g/100mLIntravenousSandoz1984-08-02Not applicableUs
NafcillinInjection, powder, for solution2 g/1Intramuscular; IntravenousSandoz1984-08-02Not applicableUs
NafcillinInjection, powder, for solution1 g/4mLIntramuscular; IntravenousSagent Pharmaceuticals2012-10-25Not applicableUs
NafcillinInjection, powder, for solution10 g/100mLIntravenousSandoz1984-08-02Not applicableUs
NafcillinInjection, powder, for solution10 g/100mLIntravenousAPP Pharmaceuticals, Inc.2011-04-27Not applicableUs
NafcillinInjection, powder, for solution10 g/100mLIntravenousWG Critical Care, LLC2011-04-27Not applicableUs
NafcillinInjection, powder, for solution10 g/100mLIntravenousHospira, Inc.1984-08-02Not applicableUs
NafcillinPowder, for solution1 g/1Intramuscular; IntravenousWG Critical Care, LLC2013-01-18Not applicableUs
NafcillinInjection, powder, for solution10 g/100mLIntravenousSagent Pharmaceuticals2012-10-25Not applicableUs
NafcillinInjection, powder, for solution2 g/8mLIntramuscular; IntravenousAuro Medics Pharma Llc2012-12-26Not applicableUs
International/Other Brands
Nallpen / Unipen
Categories
UNII
4CNZ27M7RV
CAS number
147-52-4
Weight
Average: 414.475
Monoisotopic: 414.124942514
Chemical Formula
C21H22N2O5S
InChI Key
GPXLMGHLHQJAGZ-JTDSTZFVSA-N
InChI
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
IUPAC Name
(2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OCC)C=CC2=CC=CC=C12)C(O)=O

Pharmacology

Indication

Indicated in the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug.

Associated Conditions
Pharmacodynamics

Nafcillin is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. The drugs in this class are highly resistant to inactivation by staphylococcal penicillinase and are active against penicillinase-producing and non penicillinase-producing strains of Staphylococcus species.

Mechanism of action

Like other penicillins, nafcillin exerts a bactericidal action against penicillin-susceptible microorganisms during the state of active multiplication in the bacterial cell wall synthesis [FDA Label]. It inhibits the biosynthesis of the bacterial cell wall by forming covalent bonds with penicillin-binding proteins that play a critical role in the final transpeptidation process. Binding to penicillin-binding proteins inhibits the transpeptidase and carboxypeptidase activities conferred by these proteins and prevents the formation of the crosslinks [4].

TargetActionsOrganism
APenicillin-binding protein 1b
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2a
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Absorption

Following intravenous administration of 500mg nafcillin, the mean plasma concentration was approximately 30 µg/mL. This value was reached after 5 minutes of injection [FDA Label].

Volume of distribution

Nafcillin is reported to be widely distributed in various body fluids, including bile, pleural, amniotic and synovial fluids [FDA Label].

Protein binding

The degree of nafcillin binding to serum proteins is 89.9 ± 1.5%, where it is mainly bound to albumin [FDA Label].

Metabolism

Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins.

Route of elimination

Nafcillin is primarily eliminated by non-renal routes, namely hepatic inactivation and excretion in the bile.

Half life

The serum half-life of nafcillin administered by the intravenous route ranged from 33 to 61 minutes as measured in three separate studies.

Clearance
Not Available
Toxicity

Serious toxicity is unlikely following large doses of nafcillin. Acute ingestion of large doses of nafcillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses. The oral LD50 in rats is >5000mg/kg and the intravenous LD50 in rats is >1000mg/kg [MSDS].

Affected organisms
  • Enteric bacteria and other eubacteria
  • Staphylococcus aureus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcemetacinAcemetacin may decrease the excretion rate of Nafcillin which could result in a higher serum level.Approved, Experimental, Investigational
AcenocoumarolNafcillin may decrease the anticoagulant activities of Acenocoumarol.Approved, Investigational
AgmatineThe therapeutic efficacy of Agmatine can be decreased when used in combination with Nafcillin.Experimental, Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Nafcillin.Approved, Investigational, Vet Approved
AmiodaroneThe therapeutic efficacy of Amiodarone can be decreased when used in combination with Nafcillin.Approved, Investigational
AmlodipineThe therapeutic efficacy of Amlodipine can be decreased when used in combination with Nafcillin.Approved
AmrinoneThe therapeutic efficacy of Amrinone can be decreased when used in combination with Nafcillin.Approved
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Nafcillin.Experimental, Vet Approved
AranidipineThe therapeutic efficacy of Aranidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Nafcillin.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Nafcillin.Approved, Investigational
AsunaprevirThe serum concentration of Asunaprevir can be decreased when it is combined with Nafcillin.Approved, Investigational, Withdrawn
AzelnidipineThe therapeutic efficacy of Azelnidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
AzimilideThe therapeutic efficacy of Azimilide can be decreased when used in combination with Nafcillin.Investigational
BarnidipineThe therapeutic efficacy of Barnidipine can be decreased when used in combination with Nafcillin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Nafcillin.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Nafcillin.Experimental
BencyclaneThe therapeutic efficacy of Bencyclane can be decreased when used in combination with Nafcillin.Experimental
BenidipineThe therapeutic efficacy of Benidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
BepridilThe therapeutic efficacy of Bepridil can be decreased when used in combination with Nafcillin.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Bioallethrin can be decreased when used in combination with Nafcillin.Approved, Experimental
CarboxyamidotriazoleThe therapeutic efficacy of Carboxyamidotriazole can be decreased when used in combination with Nafcillin.Investigational
CaroverineThe therapeutic efficacy of Caroverine can be decreased when used in combination with Nafcillin.Experimental
ChlortetracyclineThe therapeutic efficacy of Nafcillin can be decreased when used in combination with Chlortetracycline.Approved, Investigational, Vet Approved
CilnidipineThe therapeutic efficacy of Cilnidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
CinnarizineThe therapeutic efficacy of Cinnarizine can be decreased when used in combination with Nafcillin.Approved, Investigational
ClevidipineThe therapeutic efficacy of Clevidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
ClorindioneNafcillin may decrease the anticoagulant activities of Clorindione.Experimental
CyclandelateThe therapeutic efficacy of Cyclandelate can be decreased when used in combination with Nafcillin.Approved
CyclosporineThe metabolism of Cyclosporine can be increased when combined with Nafcillin.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Darodipine can be decreased when used in combination with Nafcillin.Experimental
DemeclocyclineThe therapeutic efficacy of Nafcillin can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Nafcillin.Experimental
DicoumarolNafcillin may decrease the anticoagulant activities of Dicoumarol.Approved
DiethylstilbestrolThe metabolism of Diethylstilbestrol can be increased when combined with Nafcillin.Approved, Investigational
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Nafcillin.Investigational, Vet Approved
DiltiazemThe therapeutic efficacy of Diltiazem can be decreased when used in combination with Nafcillin.Approved, Investigational
DiphenadioneNafcillin may decrease the anticoagulant activities of Diphenadione.Experimental
DotarizineThe therapeutic efficacy of Dotarizine can be decreased when used in combination with Nafcillin.Investigational
DoxycyclineThe therapeutic efficacy of Nafcillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EfonidipineThe therapeutic efficacy of Efonidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
EperisoneThe therapeutic efficacy of Eperisone can be decreased when used in combination with Nafcillin.Approved, Investigational
EstradiolThe metabolism of Estradiol can be increased when combined with Nafcillin.Approved, Investigational, Vet Approved
Estradiol cypionateThe metabolism of Estradiol cypionate can be increased when combined with Nafcillin.Approved, Investigational, Vet Approved
Estradiol valerateThe metabolism of Estradiol valerate can be increased when combined with Nafcillin.Approved, Investigational, Vet Approved
Ethinyl EstradiolThe metabolism of Ethinyl Estradiol can be increased when combined with Nafcillin.Approved
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with Nafcillin.Approved
Ethyl biscoumacetateNafcillin may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FelodipineThe therapeutic efficacy of Felodipine can be decreased when used in combination with Nafcillin.Approved, Investigational
FendilineThe therapeutic efficacy of Fendiline can be decreased when used in combination with Nafcillin.Withdrawn
Fish oilThe therapeutic efficacy of Fish oil can be decreased when used in combination with Nafcillin.Approved, Nutraceutical
FluindioneNafcillin may decrease the anticoagulant activities of Fluindione.Approved, Investigational
FlunarizineThe therapeutic efficacy of Flunarizine can be decreased when used in combination with Nafcillin.Approved
FluspirileneThe therapeutic efficacy of Fluspirilene can be decreased when used in combination with Nafcillin.Approved, Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Nafcillin.Approved
GabapentinThe therapeutic efficacy of Gabapentin can be decreased when used in combination with Nafcillin.Approved, Investigational
GallopamilThe therapeutic efficacy of Gallopamil can be decreased when used in combination with Nafcillin.Investigational
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Nafcillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Nafcillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Nafcillin.Experimental
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Nafcillin.Vet Approved
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Nafcillin.Experimental
IsradipineThe therapeutic efficacy of Isradipine can be decreased when used in combination with Nafcillin.Approved, Investigational
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Nafcillin.Approved, Investigational, Vet Approved
LacidipineThe therapeutic efficacy of Lacidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
LamotrigineThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Nafcillin.Approved, Investigational
LercanidipineThe therapeutic efficacy of Lercanidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Levetiracetam can be decreased when used in combination with Nafcillin.Approved, Investigational
LidoflazineThe therapeutic efficacy of Lidoflazine can be decreased when used in combination with Nafcillin.Experimental
LoperamideThe therapeutic efficacy of Loperamide can be decreased when used in combination with Nafcillin.Approved
Magnesium sulfateThe therapeutic efficacy of Magnesium sulfate can be decreased when used in combination with Nafcillin.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Manidipine can be decreased when used in combination with Nafcillin.Approved, Investigational
MentholThe therapeutic efficacy of Menthol can be decreased when used in combination with Nafcillin.Approved
MestranolThe metabolism of Mestranol can be increased when combined with Nafcillin.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Nafcillin.Approved
MethsuximideThe therapeutic efficacy of Methsuximide can be decreased when used in combination with Nafcillin.Approved
MibefradilThe therapeutic efficacy of Mibefradil can be decreased when used in combination with Nafcillin.Investigational, Withdrawn
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Nafcillin.Experimental
MinocyclineThe therapeutic efficacy of Nafcillin can be decreased when used in combination with Minocycline.Approved, Investigational
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Nafcillin resulting in a loss in efficacy.Approved
NaftopidilThe therapeutic efficacy of Naftopidil can be decreased when used in combination with Nafcillin.Investigational
NeamineThe serum concentration of Neamine can be decreased when it is combined with Nafcillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Nafcillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Nafcillin.Approved, Investigational
NicardipineThe therapeutic efficacy of Nicardipine can be decreased when used in combination with Nafcillin.Approved, Investigational
NifedipineThe therapeutic efficacy of Nifedipine can be decreased when used in combination with Nafcillin.Approved
NiguldipineThe therapeutic efficacy of Niguldipine can be decreased when used in combination with Nafcillin.Experimental
NiludipineThe therapeutic efficacy of Niludipine can be decreased when used in combination with Nafcillin.Experimental
NilvadipineThe therapeutic efficacy of Nilvadipine can be decreased when used in combination with Nafcillin.Approved, Investigational
NimesulideThe therapeutic efficacy of Nimesulide can be decreased when used in combination with Nafcillin.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Nimodipine can be decreased when used in combination with Nafcillin.Approved, Investigational
NisoldipineThe therapeutic efficacy of Nisoldipine can be decreased when used in combination with Nafcillin.Approved
NitrendipineThe therapeutic efficacy of Nitrendipine can be decreased when used in combination with Nafcillin.Approved, Investigational
NylidrinThe therapeutic efficacy of Nylidrin can be decreased when used in combination with Nafcillin.Approved
OtiloniumThe therapeutic efficacy of Otilonium can be decreased when used in combination with Nafcillin.Experimental, Investigational
OxytetracyclineThe therapeutic efficacy of Nafcillin can be decreased when used in combination with Oxytetracycline.Approved, Investigational, Vet Approved
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Nafcillin.Approved, Investigational
PhenindioneNafcillin may decrease the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonNafcillin may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Nafcillin.Approved
PinaveriumThe therapeutic efficacy of Pinaverium can be decreased when used in combination with Nafcillin.Approved
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Nafcillin.Investigational
PrenylamineThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Nafcillin.Withdrawn
ProbenecidThe serum concentration of Nafcillin can be increased when it is combined with Probenecid.Approved, Investigational
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Nafcillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Nafcillin.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Nafcillin.Approved
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Nafcillin.Approved
SeletracetamThe therapeutic efficacy of Seletracetam can be decreased when used in combination with Nafcillin.Investigational
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Nafcillin.Investigational
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Nafcillin.Approved, Vet Approved
TerodilineThe therapeutic efficacy of Terodiline can be decreased when used in combination with Nafcillin.Experimental
TetracyclineThe therapeutic efficacy of Nafcillin can be decreased when used in combination with Tetracycline.Approved, Vet Approved
TetrahydropalmatineThe therapeutic efficacy of Tetrahydropalmatine can be decreased when used in combination with Nafcillin.Investigational
TioclomarolNafcillin may decrease the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Nafcillin.Approved, Investigational
Tolfenamic AcidThe therapeutic efficacy of Tolfenamic Acid can be decreased when used in combination with Nafcillin.Approved, Investigational
TranilastThe therapeutic efficacy of Tranilast can be decreased when used in combination with Nafcillin.Approved, Investigational
TrimebutineThe therapeutic efficacy of Trimebutine can be decreased when used in combination with Nafcillin.Approved
TrimethadioneThe therapeutic efficacy of Trimethadione can be decreased when used in combination with Nafcillin.Approved
VerapamilThe therapeutic efficacy of Verapamil can be decreased when used in combination with Nafcillin.Approved
VinpocetineThe therapeutic efficacy of Vinpocetine can be decreased when used in combination with Nafcillin.Investigational
WarfarinNafcillin may decrease the anticoagulant activities of Warfarin.Approved
WIN 55212-2The therapeutic efficacy of WIN 55212-2 can be decreased when used in combination with Nafcillin.Experimental
ZiconotideThe therapeutic efficacy of Ziconotide can be decreased when used in combination with Nafcillin.Approved
ZonisamideThe therapeutic efficacy of Zonisamide can be decreased when used in combination with Nafcillin.Approved, Investigational
Food Interactions
Not Available

References

General References
  1. Blumenthal KG, Parker RA, Shenoy ES, Walensky RP: Improving Clinical Outcomes in Patients With Methicillin-Sensitive Staphylococcus aureus Bacteremia and Reported Penicillin Allergy. Clin Infect Dis. 2015 Sep 1;61(5):741-9. doi: 10.1093/cid/civ394. Epub 2015 May 19. [PubMed:25991471]
  2. Viehman JA, Oleksiuk LM, Sheridan KR, Byers KE, He P, Falcione BA, Shields RK: Adverse Events Lead to Drug Discontinuation More Commonly among Patients Who Receive Nafcillin than among Those Who Receive Oxacillin. Antimicrob Agents Chemother. 2016 Apr 22;60(5):3090-5. doi: 10.1128/AAC.03122-15. Print 2016 May. [PubMed:26976858]
  3. Youngster I, Shenoy ES, Hooper DC, Nelson SB: Comparative evaluation of the tolerability of cefazolin and nafcillin for treatment of methicillin-susceptible Staphylococcus aureus infections in the outpatient setting. Clin Infect Dis. 2014 Aug 1;59(3):369-75. doi: 10.1093/cid/ciu301. Epub 2014 Apr 29. [PubMed:24785233]
  4. 49. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 612). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
External Links
Human Metabolome Database
HMDB0014745
KEGG Compound
C07250
PubChem Compound
8982
PubChem Substance
46508100
ChemSpider
8634
BindingDB
50103525
ChEBI
7447
ChEMBL
CHEMBL1443
Therapeutic Targets Database
DAP001166
PharmGKB
PA450576
HET
NFN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Nafcillin
ATC Codes
J01CR50 — Combinations of penicillinsJ01CF06 — Nafcillin
FDA label
Download (84.8 KB)
MSDS
Download (30.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
2CompletedTreatmentBacteremia1
2CompletedTreatmentOsteomyelitis1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
3Active Not RecruitingTreatmentBacteremia1
3CompletedTreatmentAcute Hematogenous Osteomyelitis1
4CompletedTreatmentSkin Diseases, Infectious1
4RecruitingTreatmentBone Infection / Joint Infections / Osteomyelitis / Prosthetic Joint Infection / Septic Arthritis1
4TerminatedTreatmentImpaired Renal Function / S. Aureus Bacteremia / Skin and Subcutaneous Tissue Bacterial Infections1

Pharmacoeconomics

Manufacturers
  • Wyeth ayerst laboratories
  • Apothecon inc div bristol myers squibb
  • Marsam pharmaceuticals llc
  • Sandoz inc
  • Glaxosmithkline
  • Baxter healthcare corp
Packagers
  • Baxter International Inc.
  • Cardinal Health
  • Mead Johnson and Co.
  • Sandoz
Dosage forms
FormRouteStrength
InjectionIntramuscular; Intravenous1 g/1
InjectionIntramuscular; Intravenous2 g/1
Injection, powder, for solutionIntramuscular; Intravenous1 g/4mL
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionIntramuscular; Intravenous2 g/1
Injection, powder, for solutionIntramuscular; Intravenous2 g/8mL
Injection, powder, for solutionIntravenous10 g/100mL
Injection, solutionIntravenous1 g/50mL
Injection, solutionIntravenous2 g/100mL
Powder, for solutionIntramuscular; Intravenous1 g/4mL
Powder, for solutionIntramuscular; Intravenous1 g/1
Powder, for solutionIntramuscular; Intravenous2 g/1
Powder, for solutionIntramuscular; Intravenous2 g/8mL
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous2 g/1
Powder, for solutionIntramuscular; Intravenous500 mg
Prices
Unit descriptionCostUnit
Nafcillin 10 gm vial118.01USD vial
Nafcillin 2 gm vial24.08USD vial
Nafcillin 1 gm vial12.41USD vial
Nafcillin 1 gm/ 50 ml inj0.43USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0172 mg/mLALOGPS
logP3.21ALOGPS
logP2.29ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.14 m3·mol-1ChemAxon
Polarizability42.22 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5328
Blood Brain Barrier-0.9938
Caco-2 permeable-0.6248
P-glycoprotein substrateSubstrate0.708
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8807
Renal organic cation transporterNon-inhibitor0.923
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8164
CYP450 2C9 inhibitorNon-inhibitor0.7263
CYP450 2D6 inhibitorNon-inhibitor0.8869
CYP450 2C19 inhibitorNon-inhibitor0.8082
CYP450 3A4 inhibitorInhibitor0.5653
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7437
Ames testNon AMES toxic0.796
CarcinogenicityNon-carcinogens0.6679
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.1208 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9994
hERG inhibition (predictor II)Non-inhibitor0.6449
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0090000000-65901bf6905f35a84f24
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-006x-0090000000-517308aedcbe6210d46e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dl-8390000000-c3d759b208856f69cc83
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-9210000000-3431effabf1bb94e4b20
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-9200000000-8d4bae5167cd78d8f059
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-9200000000-00cc24f858c63f2e6ac5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-9500000000-d447304de567843fa59a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00xr-9500000000-fbdf096e0285a04fc391
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0600-9300000000-976ae9913f6b5bc3f293
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-80966e1fb91b5e682c61
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0910000000-04c58a908553834f1db1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00dj-0900000000-9ab759b60ea1b1ccb0a7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0900000000-1e9b29becf8d78e99cfa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00xu-0900000000-dbba294d0a77e44851ed
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-9ac2c1b4dcbf3f1421d9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-1900000000-46b494a78d0ebbbc8079
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-7900000000-dc8fdcb9afe3b064db85
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-02ti-9300000000-847a94b299fb6ea1ddca

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Penicillins / N-acyl-alpha amino acids and derivatives / Naphthalenecarboxamides / Alkyl aryl ethers / Tertiary carboxylic acid amides / Thiazolidines / Secondary carboxylic acid amides / Azetidines / Thiohemiaminal derivatives / Azacyclic compounds
show 8 more
Substituents
Alpha-dipeptide / Penicillin / 1-naphthalenecarboxylic acid or derivatives / N-acyl-alpha amino acid or derivatives / 1-naphthalenecarboxamide / Alpha-amino acid or derivatives / Naphthalene / Penam / Alkyl aryl ether / Benzenoid
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:7447)

Targets

Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transferase activity, transferring acyl groups
Specific Function
Not Available
Gene Name
pbp1b
Uniprot ID
Q7CRA4
Uniprot Name
Penicillin-binding protein 1b
Molecular Weight
89479.92 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
Penicillin binding
Gene Name
penA
Uniprot ID
P0A3M6
Uniprot Name
Penicillin-binding protein 2B
Molecular Weight
73872.305 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transferase activity, transferring acyl groups
Specific Function
Not Available
Gene Name
pbp2a
Uniprot ID
Q8DNB6
Uniprot Name
Penicillin-binding protein 2a
Molecular Weight
80797.94 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not Available
Gene Name
pbp3
Uniprot ID
Q75Y35
Uniprot Name
Penicillin-binding protein 3
Molecular Weight
45209.84 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Cell wall formation.
Gene Name
pbpA
Uniprot ID
Q8DR59
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
79700.9 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Yasuda K, Ranade A, Venkataramanan R, Strom S, Chupka J, Ekins S, Schuetz E, Bachmann K: A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97. doi: 10.1124/dmd.108.020701. Epub 2008 May 27. [PubMed:18505790]
  2. Kim KY, Frey RJ, Epplen K, Foruhari F: Interaction between warfarin and nafcillin: case report and review of the literature. Pharmacotherapy. 2007 Oct;27(10):1467-70. [PubMed:17896903]
  3. Lang CC, Jamal SK, Mohamed Z, Mustafa MR, Mustafa AM, Lee TC: Evidence of an interaction between nifedipine and nafcillin in humans. Br J Clin Pharmacol. 2003 Jun;55(6):588-90. [PubMed:12814453]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 09:29