Naftifine is an antifungal agent used to treat infections of the Tinea, Trichophyton, and Epidermophyton species.
- Brand Names
- Generic Name
- DrugBank Accession Number
Naftifine 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.
- Small Molecule
- Average: 287.3981
- Chemical Formula
- External IDs
- AW 105 843
- SN 105843
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.Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset
- Associated Conditions
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Naftifine 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 action
Although 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.
Target Actions Organism ASqualene monooxygenaseinhibitor Humans
Following 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 distribution
- Protein binding
- Not Available
- Route of elimination
Naftifine and/or its metabolites are excreted via the urine and feces with a half-life of approximately two to three days.
Approximately 2 to 3 days following topical administration.
- Adverse Effects
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- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.No interactions found.
- Food Interactions
- No interactions found.
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- Product Ingredients
Ingredient UNII CAS InChI Key Naftifine Hydrochloride 25UR9N9041 65473-14-5 OLUNPKFOFGZHRT-YGCVIUNWSA-N
- International/Other Brands
- A Mei (Shou Chan) / Ancent (Yuan Chou) / Exoderil (Sandoz) / Micosona (Bayer) / Naftifina (Antibiotice) / Suadian (Sandoz)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Naftifine Hydrochloride Cream 20 mg/1g Topical Renaissance Pharma, Inc. 2016-02-01 2021-08-31 Naftifine Hydrochloride Cream 1 mg/1g Topical Renaissance Pharma, Inc. 2016-10-01 2020-04-30 Naftin Gel 10 mg/1g Topical Merz Pharmaceuticals 1990-10-01 2016-12-01 Naftin Cream 10 mg/1g Topical Merz Pharmaceuticals 1998-06-01 Not applicable Naftin Gel 10 mg/1g Topical Sebela Pharmaceuticals Inc. 2018-01-22 Not applicable Naftin Cream 10 mg/2g Topical Merz Pharmaceuticals 2012-03-01 2016-12-01 Naftin Cream 10 mg/1g Topical Physicians Total Care, Inc. 2010-06-17 Not applicable Naftin Gel 2 g/100g Topical Merz Pharmaceuticals 2013-09-01 2016-12-01 Naftin Gel 10 mg/1g Topical Physicians Total Care, Inc. 2005-12-29 Not applicable Naftin Gel 2 g/100g Topical Sebela Pharmaceuticals Inc. 2018-03-01 Not applicable
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Naftifine hydrochloride Cream 20 mg/1g Topical Xiromed, Llc 2021-01-15 Not applicable Naftifine Hydrochloride Cream 20 mg/1g Topical Amneal Pharmaceuticals of New York Llc 2017-05-10 Not applicable Naftifine Hydrochloride Gel 20 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2019-04-10 Not applicable Naftifine Hydrochloride Cream 10 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2016-09-08 Not applicable Naftifine Hydrochloride Gel 10 mg/1g Topical Amneal Pharmaceuticals of New York Llc 2019-03-20 Not applicable Naftifine Hydrochloride Cream 20 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2016-01-06 Not applicable
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image EXODERIL CREAM 1 % Cream Topical NOVARTIS CORPORATION (MALAYSIA) SDN. BHD. 2020-09-08 Not applicable Naftin Crm 1% Cream 1 % Topical Allergan Herbert Skin Care Division Of Allergan Inc. 1993-12-31 2011-08-04 Naftin Gel 1% Gel 1 % Topical Allergan Herbert Skin Care Division Of Allergan Inc. 1993-12-31 2011-08-04
- ATC Codes
- D01AE22 — Naftifine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- This 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.
- Organic compounds
- Super Class
- Sub Class
- Not Available
- Direct Parent
- Alternative Parents
- Styrenes / Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Amine / Aralkylamine / Aromatic homopolycyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Naphthalene / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Styrene
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Yeast and other fungi
- CAS number
- InChI Key
- IUPAC Name
- Synthesis Reference
- General References
- Not Available
- Download (14.2 KB)
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Tinea Corporis 2 4 Completed Treatment Tinea Cruris / Tinea Pedis 1 3 Completed Treatment Tinea Cruris 1 3 Completed Treatment Tinea Pedis 4 2 Completed Treatment Onychomycosis 1 2 Withdrawn Treatment Tinea Capitis 1 1 Completed Treatment Tinea Pedis 3
- Merz pharmaceuticals llc
- DPT Laboratories Ltd.
- Merz Pharmaceuticals LLC
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Spray Topical Cream Topical Solution Topical Cream Topical 1 mg/1g Cream Topical 20 mg/1g Gel Topical 20 mg/1g Cream Topical 10 mg/2g Cream Topical 10 mg/1g Gel Topical 10 mg/1g Gel Topical 2 g/100g Cream Topical 1 % Gel Topical 1 % Gel Topical
Unit description Cost Unit Naftin 1% Gel 90 gm Tube 290.08USD tube Naftin 1% Cream 90 gm Tube 248.26USD tube Naftin 1% Gel 60 gm Tube 208.5USD tube Naftin 1% Cream 60 gm Tube 183.77USD tube Naftin 1% Gel 40 gm Tube 147.0USD tube Naftin 1% Cream 30 gm Tube 101.62USD tube Naftin pump 1% cream 3.2USD g Naftin 1% cream 2.45USD gDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent Number Pediatric Extension Approved Expires (estimated) Region US9161914 No 2015-10-20 2033-01-31 US8778365 No 2014-07-15 2033-01-31 US10166206 No 2019-01-01 2033-01-31 US10166205 No 2019-01-01 2033-01-31 US10695303 No 2013-01-31 2033-01-31 US10729667 No 2013-01-31 2033-01-31
- Experimental Properties
Property Value Source logP 5.4 Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000229 mg/mL ALOGPS logP 4.96 ALOGPS logP 5.24 ChemAxon logS -6.1 ALOGPS pKa (Strongest Basic) 9.08 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 3.24 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 95.98 m3·mol-1 ChemAxon Polarizability 34.05 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon
- Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9968 Blood Brain Barrier + 0.9713 Caco-2 permeable + 0.812 P-glycoprotein substrate Substrate 0.525 P-glycoprotein inhibitor I Non-inhibitor 0.8649 P-glycoprotein inhibitor II Inhibitor 0.6605 Renal organic cation transporter Inhibitor 0.5834 CYP450 2C9 substrate Non-substrate 0.7661 CYP450 2D6 substrate Non-substrate 0.829 CYP450 3A4 substrate Non-substrate 0.5646 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Non-inhibitor 0.876 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6083 Ames test Non AMES toxic 0.5561 Carcinogenicity Non-carcinogens 0.6525 Biodegradation Not ready biodegradable 0.9926 Rat acute toxicity 2.5407 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6159 hERG inhibition (predictor II) Non-inhibitor 0.6593
- Mass Spec (NIST)
- Not Available
- Pharmacological action
- 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
- Uniprot ID
- Uniprot Name
- Squalene monooxygenase
- Molecular Weight
- 63922.505 Da
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [Article]
Drug created on June 13, 2005 13:24 / Updated on March 04, 2021 11:34