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Identification
NameNaftifine
Accession NumberDB00735  (APRD01131)
TypeSmall Molecule
GroupsApproved
DescriptionNaftifine is a synthetic, broad spectrum, antifungal agent and allylamine derivative for the topical treatment of tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans and Epidermophyton floccosum.
Structure
Thumb
Synonyms
Naftifin
Naftifina
Naftifine
Naftifinum
Naftin
External Identifiers
  • AW 105 843
  • SN 105843
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naftifine Hydrochloridecream20 mg/gtopicalRenaissance Pharma, Inc2016-02-01Not applicableUs
Naftifine Hydrochloridecream1 mg/gtopicalRenaissance Pharma, Inc2015-06-01Not applicableUs
Naftincream10 mg/2gtopicalMerz Pharmaceuticals, LLC2012-03-01Not applicableUs
Naftingel2 g/100gtopicalMerz Pharmaceuticals, LLC2013-09-01Not applicableUs
Naftingel10 mg/gtopicalPhysicians Total Care, Inc.2005-12-29Not applicableUs
Naftincream10 mg/gtopicalMerz Pharmaceuticals, LLC1998-06-01Not applicableUs
Naftincream10 mg/gtopicalPhysicians Total Care, Inc.2010-06-17Not applicableUs
Naftingel10 mg/gtopicalMerz Pharmaceuticals, LLC1990-10-01Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naftifine Hydrochloridecream20 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2016-01-06Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naftin Crm 1%cream1 %topicalAllergan Herbert Skin Care Division Of Allergan Inc.1993-12-312011-08-04Canada
Naftin Gel 1%gel1 %topicalAllergan Herbert Skin Care Division Of Allergan Inc.1993-12-312011-08-04Canada
Unapproved/Other Products Not Available
International Brands
NameCompany
A MeiShou Chan
AncentYuan Chou
ExoderilSandoz
MicosonaBayer
NaftifinaAntibiotice
SuadianSandoz
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Naftifine Hydrochloride
Thumb
  • InChI Key: OLUNPKFOFGZHRT-YGCVIUNWSA-N
  • Monoisotopic Mass: 323.144077416
  • Average Mass: 323.859
DBSALT000677
Categories
UNII4FB1TON47A
CAS number65472-88-0
WeightAverage: 287.3981
Monoisotopic: 287.167399677
Chemical FormulaC21H21N
InChI KeyInChIKey=OZGNYLLQHRPOBR-DHZHZOJOSA-N
InChI
InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+
IUPAC Name
methyl(naphthalen-1-ylmethyl)(3-phenylprop-2-en-1-yl)amine
SMILES
CN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Phenylpropene
  • Styrene
  • Benzylamine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the topical treatment of tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans and Epidermophyton floccosum.
PharmacodynamicsNaftifine is a synthetic, broad spectrum, antifungal agent and allylamine derivative. The following in vitro data are available, but their clinical significance is unknown. Naftifine has been shown to exhibit fungicidal activity in vitro against a broad spectrum of organisms including Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, Epidermophyton floccosum, and Microsporum canis, Microsporum audouini, and Microsporum gypseum; and fungistatic activity against Candida species including Candida albicans. However it is only used to treat the organisms listed in the indications.
Mechanism of actionAlthough the exact mechanism of action against fungi is not known, naftifine appears to interfere with sterol biosynthesis by inhibiting the enzyme squalene 2,3-epoxidase. This inhibition of enzyme activity results in decreased amounts of sterols, especially ergosterol, and a corresponding accumulation of squalene in the cells.
Related Articles
AbsorptionFollowing single topical applications of 3H-labeled naftifine gel 1% to the skin of healthy subjects, up to 4.2% of the applied dose was absorbed.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNaftifine and/or its metabolites are excreted via the urine and feces with a half-life of approximately two to three days.
Half lifeApproximately 2 to 3 days following topical administration.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Yeast and other fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9968
Blood Brain Barrier+0.9713
Caco-2 permeable+0.812
P-glycoprotein substrateSubstrate0.525
P-glycoprotein inhibitor INon-inhibitor0.8649
P-glycoprotein inhibitor IIInhibitor0.6605
Renal organic cation transporterInhibitor0.5834
CYP450 2C9 substrateNon-substrate0.7661
CYP450 2D6 substrateNon-substrate0.829
CYP450 3A4 substrateNon-substrate0.5646
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorNon-inhibitor0.876
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6083
Ames testNon AMES toxic0.5561
CarcinogenicityNon-carcinogens0.6525
BiodegradationNot ready biodegradable0.9926
Rat acute toxicity2.5407 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6159
hERG inhibition (predictor II)Non-inhibitor0.6593
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Merz pharmaceuticals llc
Packagers
Dosage forms
FormRouteStrength
Creamtopical1 mg/g
Creamtopical20 mg/g
Creamtopical10 mg/2g
Creamtopical10 mg/g
Geltopical10 mg/g
Geltopical2 g/100g
Creamtopical1 %
Geltopical1 %
Prices
Unit descriptionCostUnit
Naftin 1% Gel 90 gm Tube290.08USD tube
Naftin 1% Cream 90 gm Tube248.26USD tube
Naftin 1% Gel 60 gm Tube208.5USD tube
Naftin 1% Cream 60 gm Tube183.77USD tube
Naftin 1% Gel 40 gm Tube147.0USD tube
Naftin 1% Cream 30 gm Tube101.62USD tube
Naftin pump 1% cream3.2USD g
Naftin 1% cream2.45USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8778365 No2013-01-312033-01-31Us
US9161914 No2013-01-312033-01-31Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP5.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000229 mg/mLALOGPS
logP4.96ALOGPS
logP5.24ChemAxon
logS-6.1ALOGPS
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.98 m3·mol-1ChemAxon
Polarizability34.05 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US4282251
General ReferencesNot Available
External Links
ATC CodesD01AE22
AHFS Codes
  • 84:04.08.04
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (14.2 KB)
Interactions
Drug Interactions
Drug
AbciximabNaftifine may increase the anticoagulant activities of Abciximab.
AcebutololNaftifine may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Naftifine is combined with Aceclofenac.
AcenocoumarolNaftifine may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Acetylsalicylic acid.
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Naftifine.
Alendronic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Alendronic acid.
AliskirenNaftifine may decrease the antihypertensive activities of Aliskiren.
AlprenololNaftifine may decrease the antihypertensive activities of Alprenolol.
AlprostadilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Naftifine.
AmikacinNaftifine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmilorideNaftifine may decrease the antihypertensive activities of Amiloride.
AmlodipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Amlodipine.
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Naftifine.
AmrinoneThe risk or severity of adverse effects can be increased when Naftifine is combined with Amrinone.
AncrodNaftifine may increase the anticoagulant activities of Ancrod.
AntipyrineThe risk or severity of adverse effects can be increased when Naftifine is combined with Antipyrine.
Antithrombin III humanNaftifine may increase the anticoagulant activities of Antithrombin III human.
ApixabanNaftifine may increase the anticoagulant activities of Apixaban.
ApremilastThe risk or severity of adverse effects can be increased when Naftifine is combined with Apremilast.
ArdeparinNaftifine may increase the anticoagulant activities of Ardeparin.
ArgatrobanNaftifine may increase the anticoagulant activities of Argatroban.
ArotinololNaftifine may decrease the antihypertensive activities of Arotinolol.
AtenololNaftifine may decrease the antihypertensive activities of Atenolol.
AzapropazoneThe risk or severity of adverse effects can be increased when Naftifine is combined with Azapropazone.
AzelastineThe risk or severity of adverse effects can be increased when Naftifine is combined with Azelastine.
AzelnidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Azelnidipine.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Naftifine.
AzimilideThe risk or severity of adverse effects can be increased when Naftifine is combined with Azimilide.
BalsalazideNaftifine may increase the nephrotoxic activities of Balsalazide.
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Naftifine.
BarnidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Barnidipine.
BecaplerminNaftifine may increase the anticoagulant activities of Becaplermin.
BefunololNaftifine may decrease the antihypertensive activities of Befunolol.
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Naftifine.
BendroflumethiazideThe therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Naftifine.
BenidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Benidipine.
BenoxaprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Benoxaprofen.
BepridilThe risk or severity of adverse effects can be increased when Naftifine is combined with Bepridil.
BetaxololNaftifine may decrease the antihypertensive activities of Betaxolol.
BevantololNaftifine may decrease the antihypertensive activities of Bevantolol.
BimatoprostThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Naftifine.
BisoprololNaftifine may decrease the antihypertensive activities of Bisoprolol.
BivalirudinNaftifine may increase the anticoagulant activities of Bivalirudin.
BopindololNaftifine may decrease the antihypertensive activities of Bopindolol.
BromfenacThe risk or severity of adverse effects can be increased when Naftifine is combined with Bromfenac.
BufuralolNaftifine may decrease the antihypertensive activities of Bufuralol.
BumetanideNaftifine may decrease the diuretic activities of Bumetanide.
BupranololNaftifine may decrease the antihypertensive activities of Bupranolol.
BuspironeThe metabolism of Buspirone can be decreased when combined with Naftifine.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Naftifine.
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Naftifine.
CandoxatrilThe risk or severity of adverse effects can be increased when Candoxatril is combined with Naftifine.
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Naftifine.
Carboprost TromethamineThe therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Naftifine.
CarprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Carprofen.
CarteololNaftifine may decrease the antihypertensive activities of Carteolol.
CarvedilolNaftifine may decrease the antihypertensive activities of Carvedilol.
CastanospermineThe risk or severity of adverse effects can be increased when Naftifine is combined with Castanospermine.
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Naftifine.
CeliprololNaftifine may decrease the antihypertensive activities of Celiprolol.
CertoparinNaftifine may increase the anticoagulant activities of Certoparin.
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Naftifine.
ChlorothiazideThe therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Naftifine.
ChlorthalidoneThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Naftifine.
CholestyramineCholestyramine can cause a decrease in the absorption of Naftifine resulting in a reduced serum concentration and potentially a decrease in efficacy.
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Naftifine.
CilnidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Cilnidipine.
CinnarizineThe risk or severity of adverse effects can be increased when Naftifine is combined with Cinnarizine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Naftifine.
Citric AcidNaftifine may increase the anticoagulant activities of Citric Acid.
ClodronateThe risk or severity of adverse effects can be increased when Naftifine is combined with Clodronate.
ClonixinThe risk or severity of adverse effects can be increased when Naftifine is combined with Clonixin.
CloprostenolThe therapeutic efficacy of Cloprostenol can be decreased when used in combination with Naftifine.
ColesevelamColesevelam can cause a decrease in the absorption of Naftifine resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Naftifine resulting in a reduced serum concentration and potentially a decrease in efficacy.
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Naftifine.
CyclosporineNaftifine may increase the nephrotoxic activities of Cyclosporine.
D-LimoneneThe risk or severity of adverse effects can be increased when Naftifine is combined with D-Limonene.
Dabigatran etexilateNaftifine may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinNaftifine may increase the anticoagulant activities of Dalteparin.
DanaparoidNaftifine may increase the anticoagulant activities of Danaparoid.
DarodipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Darodipine.
DaunorubicinNaftifine may decrease the excretion rate of Daunorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DeferasiroxThe risk or severity of adverse effects can be increased when Naftifine is combined with Deferasirox.
DesirudinNaftifine may increase the anticoagulant activities of Desirudin.
DesmopressinThe risk or severity of adverse effects can be increased when Naftifine is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Naftifine.
DextranNaftifine may increase the anticoagulant activities of Dextran.
Dextran 40Naftifine may increase the anticoagulant activities of Dextran 40.
Dextran 70Naftifine may increase the anticoagulant activities of Dextran 70.
Dextran 75Naftifine may increase the anticoagulant activities of Dextran 75.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Naftifine.
DicoumarolNaftifine may increase the anticoagulant activities of Dicoumarol.
DidanosineDidanosine can cause a decrease in the absorption of Naftifine resulting in a reduced serum concentration and potentially a decrease in efficacy.
DiflunisalThe risk or severity of adverse effects can be increased when Naftifine is combined with Diflunisal.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Naftifine.
DihydrostreptomycinNaftifine may decrease the excretion rate of Dihydrostreptomycin which could result in a lower serum level and potentially a reduction in efficacy.
DiltiazemThe risk or severity of adverse effects can be increased when Naftifine is combined with Diltiazem.
DinoprostoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Naftifine.
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Naftifine.
DofetilideThe metabolism of Dofetilide can be decreased when combined with Naftifine.
DotarizineThe risk or severity of adverse effects can be increased when Naftifine is combined with Dotarizine.
DoxorubicinNaftifine may decrease the excretion rate of Doxorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DrospirenoneNaftifine may increase the hyperkalemic activities of Drospirenone.
DroxicamThe risk or severity of adverse effects can be increased when Naftifine is combined with Droxicam.
Edetic AcidNaftifine may increase the anticoagulant activities of Edetic Acid.
EdoxabanNaftifine may increase the anticoagulant activities of Edoxaban.
EfonidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Efonidipine.
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Naftifine.
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Naftifine.
EnoxaparinNaftifine may increase the anticoagulant activities of Enoxaparin.
EperisoneThe risk or severity of adverse effects can be increased when Naftifine is combined with Eperisone.
EpirizoleThe risk or severity of adverse effects can be increased when Naftifine is combined with Epirizole.
EpirubicinNaftifine may decrease the excretion rate of Epirubicin which could result in a lower serum level and potentially a reduction in efficacy.
EplerenoneNaftifine may decrease the antihypertensive activities of Eplerenone.
EpoprostenolThe therapeutic efficacy of Epoprostenol can be decreased when used in combination with Naftifine.
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Naftifine.
EsmololNaftifine may decrease the antihypertensive activities of Esmolol.
Etacrynic acidNaftifine may decrease the diuretic activities of Etacrynic acid.
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Naftifine.
Ethyl biscoumacetateNaftifine may increase the anticoagulant activities of Ethyl biscoumacetate.
Etidronic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Etidronic acid.
EtodolacThe risk or severity of adverse effects can be increased when Naftifine is combined with Etodolac.
EtofenamateThe risk or severity of adverse effects can be increased when Naftifine is combined with Etofenamate.
EtoricoxibThe risk or severity of adverse effects can be increased when Naftifine is combined with Etoricoxib.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Naftifine.
Evening primrose oilThe risk or severity of adverse effects can be increased when Naftifine is combined with Evening primrose oil.
exisulindThe risk or severity of adverse effects can be increased when Naftifine is combined with exisulind.
FelodipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Felodipine.
FenbufenThe risk or severity of adverse effects can be increased when Naftifine is combined with Fenbufen.
FendilineThe risk or severity of adverse effects can be increased when Naftifine is combined with Fendiline.
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Naftifine.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Naftifine.
FlunarizineThe risk or severity of adverse effects can be increased when Naftifine is combined with Flunarizine.
FlunixinThe risk or severity of adverse effects can be increased when Naftifine is combined with Flunixin.
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Naftifine.
Folic AcidThe therapeutic efficacy of Folic Acid can be decreased when used in combination with Naftifine.
Fondaparinux sodiumNaftifine may increase the anticoagulant activities of Fondaparinux sodium.
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Naftifine.
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Naftifine.
FosphenytoinThe serum concentration of Naftifine can be decreased when it is combined with Fosphenytoin.
FramycetinNaftifine may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FurosemideNaftifine may decrease the diuretic activities of Furosemide.
GabapentinThe risk or severity of adverse effects can be increased when Naftifine is combined with Gabapentin.
GemeprostThe therapeutic efficacy of Gemeprost can be decreased when used in combination with Naftifine.
GentamicinNaftifine may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
HaloperidolThe risk or severity of adverse effects can be increased when Naftifine is combined with Haloperidol.
HeparinNaftifine may increase the anticoagulant activities of Heparin.
HirulogNaftifine may increase the anticoagulant activities of Hirulog.
HMPL-004The risk or severity of adverse effects can be increased when Naftifine is combined with HMPL-004.
HydralazineNaftifine may decrease the antihypertensive activities of Hydralazine.
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Naftifine.
HydroflumethiazideThe therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Naftifine.
Hygromycin BNaftifine may decrease the excretion rate of Hygromycin B which could result in a lower serum level and potentially a reduction in efficacy.
IbandronateThe risk or severity of adverse effects can be increased when Naftifine is combined with Ibandronate.
IbuprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Ibuprofen.
IbuproxamThe risk or severity of adverse effects can be increased when Naftifine is combined with Ibuproxam.
IcatibantThe risk or severity of adverse effects can be increased when Naftifine is combined with Icatibant.
IdarubicinNaftifine may decrease the excretion rate of Idarubicin which could result in a lower serum level and potentially a reduction in efficacy.
IloprostThe therapeutic efficacy of Iloprost can be decreased when used in combination with Naftifine.
IndapamideThe therapeutic efficacy of Indapamide can be decreased when used in combination with Naftifine.
IndenololNaftifine may decrease the antihypertensive activities of Indenolol.
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Naftifine.
IndoprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Indoprofen.
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Naftifine.
IsoxicamThe risk or severity of adverse effects can be increased when Naftifine is combined with Isoxicam.
IsradipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Isradipine.
KanamycinNaftifine may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KebuzoneThe risk or severity of adverse effects can be increased when Naftifine is combined with Kebuzone.
KetoprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Naftifine.
LabetalolNaftifine may decrease the antihypertensive activities of Labetalol.
LacidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Lacidipine.
LamotrigineThe risk or severity of adverse effects can be increased when Naftifine is combined with Lamotrigine.
LeflunomideThe risk or severity of adverse effects can be increased when Naftifine is combined with Leflunomide.
LepirudinNaftifine may increase the anticoagulant activities of Lepirudin.
LercanidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Lercanidipine.
LevobunololNaftifine may decrease the antihypertensive activities of Levobunolol.
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Naftifine.
LithiumThe serum concentration of Lithium can be increased when it is combined with Naftifine.
LornoxicamThe risk or severity of adverse effects can be increased when Naftifine is combined with Lornoxicam.
LosartanThe metabolism of Losartan can be decreased when combined with Naftifine.
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Naftifine.
LoxoprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Loxoprofen.
LubiprostoneThe therapeutic efficacy of Lubiprostone can be decreased when used in combination with Naftifine.
LumiracoxibThe risk or severity of adverse effects can be increased when Naftifine is combined with Lumiracoxib.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Naftifine is combined with Magnesium salicylate.
Magnesium SulfateThe risk or severity of adverse effects can be increased when Naftifine is combined with Magnesium Sulfate.
ManidipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Manidipine.
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Naftifine.
Meclofenamic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Meclofenamic acid.
Mefenamic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Mefenamic acid.
MeloxicamThe risk or severity of adverse effects can be increased when Naftifine is combined with Meloxicam.
MesalazineNaftifine may increase the nephrotoxic activities of Mesalazine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Naftifine.
MetamizoleThe risk or severity of adverse effects can be increased when Naftifine is combined with Metamizole.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Naftifine.
MethyclothiazideThe therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Naftifine.
MetipranololNaftifine may decrease the antihypertensive activities of Metipranolol.
MetolazoneThe therapeutic efficacy of Metolazone can be decreased when used in combination with Naftifine.
MetoprololNaftifine may decrease the antihypertensive activities of Metoprolol.
MetrizamideNaftifine may decrease the excretion rate of Metrizamide which could result in a lower serum level and potentially a reduction in efficacy.
MibefradilThe risk or severity of adverse effects can be increased when Naftifine is combined with Mibefradil.
MisoprostolThe therapeutic efficacy of Misoprostol can be decreased when used in combination with Naftifine.
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Naftifine.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Naftifine.
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Naftifine.
Mycophenolic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Mycophenolic acid.
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Naftifine.
NadololNaftifine may decrease the antihypertensive activities of Nadolol.
NadroparinNaftifine may increase the anticoagulant activities of Nadroparin.
NaproxenThe risk or severity of adverse effects can be increased when Naftifine is combined with Naproxen.
NCX 4016The risk or severity of adverse effects can be increased when Naftifine is combined with NCX 4016.
NeomycinNaftifine may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NepafenacThe risk or severity of adverse effects can be increased when Naftifine is combined with Nepafenac.
NetilmicinNaftifine may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
NicardipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Nicardipine.
NifedipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Nifedipine.
Niflumic AcidThe risk or severity of adverse effects can be increased when Naftifine is combined with Niflumic Acid.
NiguldipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Niguldipine.
NiludipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Niludipine.
NilvadipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Nilvadipine.
NimesulideThe risk or severity of adverse effects can be increased when Naftifine is combined with Nimesulide.
NimodipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Nimodipine.
NisoldipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Nisoldipine.
NitrendipineThe risk or severity of adverse effects can be increased when Naftifine is combined with Nitrendipine.
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Naftifine.
OlopatadineThe risk or severity of adverse effects can be increased when Naftifine is combined with Olopatadine.
OlsalazineNaftifine may increase the nephrotoxic activities of Olsalazine.
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Naftifine.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Naftifine is combined with Omacetaxine mepesuccinate.
OmapatrilatThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Naftifine.
OrgoteinThe risk or severity of adverse effects can be increased when Naftifine is combined with Orgotein.
OtamixabanNaftifine may increase the anticoagulant activities of Otamixaban.
OxaprozinThe risk or severity of adverse effects can be increased when Naftifine is combined with Oxaprozin.
OxprenololNaftifine may decrease the antihypertensive activities of Oxprenolol.
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Naftifine is combined with Oxyphenbutazone.
PamidronateThe risk or severity of adverse effects can be increased when Naftifine is combined with Pamidronate.
ParecoxibThe risk or severity of adverse effects can be increased when Naftifine is combined with Parecoxib.
ParomomycinNaftifine may decrease the excretion rate of Paromomycin which could result in a lower serum level and potentially a reduction in efficacy.
PenbutololNaftifine may decrease the antihypertensive activities of Penbutolol.
Pentosan PolysulfateNaftifine may increase the anticoagulant activities of Pentosan Polysulfate.
PerhexilineThe risk or severity of adverse effects can be increased when Naftifine is combined with Perhexiline.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Naftifine.
PhenindioneNaftifine may increase the anticoagulant activities of Phenindione.
PhenprocoumonNaftifine may increase the anticoagulant activities of Phenprocoumon.
PhenylbutazoneThe risk or severity of adverse effects can be increased when Naftifine is combined with Phenylbutazone.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Naftifine.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Naftifine.
PimozideNaftifine may increase the arrhythmogenic activities of Pimozide.
PinaveriumThe risk or severity of adverse effects can be increased when Naftifine is combined with Pinaverium.
PindololNaftifine may decrease the antihypertensive activities of Pindolol.
PiretanideNaftifine may decrease the diuretic activities of Piretanide.
PirfenidoneThe risk or severity of adverse effects can be increased when Naftifine is combined with Pirfenidone.
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Naftifine.
PlicamycinNaftifine may decrease the excretion rate of Plicamycin which could result in a lower serum level and potentially a reduction in efficacy.
PolythiazideThe therapeutic efficacy of Polythiazide can be decreased when used in combination with Naftifine.
PractololNaftifine may decrease the antihypertensive activities of Practolol.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Naftifine.
PregabalinThe risk or severity of adverse effects can be increased when Naftifine is combined with Pregabalin.
PrenylamineThe risk or severity of adverse effects can be increased when Naftifine is combined with Prenylamine.
ProbenecidThe serum concentration of Naftifine can be increased when it is combined with Probenecid.
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Naftifine.
PropacetamolThe risk or severity of adverse effects can be increased when Naftifine is combined with Propacetamol.
PropranololNaftifine may decrease the antihypertensive activities of Propranolol.
Prostaglandin D2The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Naftifine.
Protein CNaftifine may increase the anticoagulant activities of Protein C.
ProtocatechualdehydeNaftifine may increase the anticoagulant activities of Protocatechualdehyde.
PTC299The risk or severity of adverse effects can be increased when Naftifine is combined with PTC299.
PuromycinNaftifine may decrease the excretion rate of Puromycin which could result in a lower serum level and potentially a reduction in efficacy.
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Naftifine.
QuinethazoneThe therapeutic efficacy of Quinethazone can be decreased when used in combination with Naftifine.
QuinidineThe metabolism of Quinidine can be decreased when combined with Naftifine.
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Naftifine.
RanolazineThe metabolism of Ranolazine can be decreased when combined with Naftifine.
RescinnamineThe risk or severity of adverse effects can be increased when Rescinnamine is combined with Naftifine.
ResveratrolThe risk or severity of adverse effects can be increased when Naftifine is combined with Resveratrol.
ReviparinNaftifine may increase the anticoagulant activities of Reviparin.
RibostamycinNaftifine may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateThe risk or severity of adverse effects can be increased when Naftifine is combined with Risedronate.
RivaroxabanNaftifine may increase the anticoagulant activities of Rivaroxaban.
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Naftifine.
SalicylamideThe risk or severity of adverse effects can be increased when Naftifine is combined with Salicylamide.
Salicylic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Salicylic acid.
SalsalateThe risk or severity of adverse effects can be increased when Naftifine is combined with Salsalate.
SaprisartanThe risk or severity of adverse effects can be increased when Saprisartan is combined with Naftifine.
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Naftifine.
SeratrodastThe risk or severity of adverse effects can be increased when Naftifine is combined with Seratrodast.
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Naftifine.
SotalolNaftifine may decrease the antihypertensive activities of Sotalol.
SpectinomycinNaftifine may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
SpiraprilThe risk or severity of adverse effects can be increased when Spirapril is combined with Naftifine.
SpironolactoneNaftifine may decrease the antihypertensive activities of Spironolactone.
SRT501The risk or severity of adverse effects can be increased when Naftifine is combined with SRT501.
StreptomycinNaftifine may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptozocinNaftifine may decrease the excretion rate of Streptozocin which could result in a lower serum level and potentially a reduction in efficacy.
SucralfateSucralfate can cause a decrease in the absorption of Naftifine resulting in a reduced serum concentration and potentially a decrease in efficacy.
SulfasalazineNaftifine may increase the nephrotoxic activities of Sulfasalazine.
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Naftifine.
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Naftifine.
SulodexideNaftifine may increase the anticoagulant activities of Sulodexide.
SunitinibThe metabolism of Sunitinib can be decreased when combined with Naftifine.
SuprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Suprofen.
TacrolimusNaftifine may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Naftifine.
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Naftifine.
Technetium Tc-99m MedronateThe risk or severity of adverse effects can be increased when Naftifine is combined with Technetium Tc-99m Medronate.
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Naftifine.
TemocaprilThe risk or severity of adverse effects can be increased when Temocapril is combined with Naftifine.
TenofovirThe risk or severity of adverse effects can be increased when Naftifine is combined with Tenofovir.
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Naftifine.
TepoxalinThe risk or severity of adverse effects can be increased when Naftifine is combined with Tepoxalin.
TeriflunomideThe risk or severity of adverse effects can be increased when Naftifine is combined with Teriflunomide.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Tiaprofenic acid.
TiludronateThe risk or severity of adverse effects can be increased when Naftifine is combined with Tiludronate.
TimololNaftifine may decrease the antihypertensive activities of Timolol.
TobramycinNaftifine may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Naftifine is combined with Tolfenamic Acid.
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Naftifine.
TorasemideNaftifine may decrease the diuretic activities of Torasemide.
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Naftifine.
TranilastThe risk or severity of adverse effects can be increased when Naftifine is combined with Tranilast.
TravoprostThe therapeutic efficacy of Travoprost can be decreased when used in combination with Naftifine.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Naftifine.
TriamtereneNaftifine may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Naftifine.
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Naftifine is combined with Trisalicylate-choline.
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Naftifine.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Naftifine.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Naftifine.
VerapamilThe risk or severity of adverse effects can be increased when Naftifine is combined with Verapamil.
WarfarinNaftifine may increase the anticoagulant activities of Warfarin.
XimelagatranNaftifine may increase the anticoagulant activities of Ximelagatran.
XylometazolineThe risk or severity of adverse effects can be increased when Naftifine is combined with Xylometazoline.
ZaltoprofenThe risk or severity of adverse effects can be increased when Naftifine is combined with Zaltoprofen.
ZiconotideThe risk or severity of adverse effects can be increased when Naftifine is combined with Ziconotide.
ZileutonThe risk or severity of adverse effects can be increased when Naftifine is combined with Zileuton.
Zoledronic acidThe risk or severity of adverse effects can be increased when Naftifine is combined with Zoledronic acid.
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Naftifine.
ZomepiracThe risk or severity of adverse effects can be increased when Naftifine is combined with Zomepirac.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Squalene monooxygenase activity
Specific Function:
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name:
SQLE
Uniprot ID:
Q14534
Molecular Weight:
63922.505 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Favre B, Ryder NS: Characterization of squalene epoxidase activity from the dermatophyte Trichophyton rubrum and its inhibition by terbinafine and other antimycotic agents. Antimicrob Agents Chemother. 1996 Feb;40(2):443-7. [PubMed:8834895 ]
  3. Vanden Bossche H, Marichal P: Mode of action of anti-Candida drugs: focus on terconazole and other ergosterol biosynthesis inhibitors. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1193-9. [PubMed:1951574 ]
  4. Mukherjee PK, Leidich SD, Isham N, Leitner I, Ryder NS, Ghannoum MA: Clinical Trichophyton rubrum strain exhibiting primary resistance to terbinafine. Antimicrob Agents Chemother. 2003 Jan;47(1):82-6. [PubMed:12499173 ]
  5. Ryder NS, Dupont MC: Inhibition of squalene epoxidase by allylamine antimycotic compounds. A comparative study of the fungal and mammalian enzymes. Biochem J. 1985 Sep 15;230(3):765-70. [PubMed:3877503 ]
  6. Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164 ]
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Drug created on June 13, 2005 07:24 / Updated on September 26, 2016 02:14