Naftifine
Identification
- Summary
Naftifine is an antifungal agent used to treat infections of the Tinea, Trichophyton, and Epidermophyton species.
- Brand Names
- Naftin
- Generic Name
- Naftifine
- DrugBank Accession Number
- DB00735
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 287.3981
Monoisotopic: 287.167399677 - Chemical Formula
- C21H21N
- Synonyms
- Naftifin
- Naftifina
- Naftifine
- Naftifinum
- External IDs
- AW 105 843
- SN 105843
Pharmacology
- Indication
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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Tinea corporis •••••••••••• ••• Treatment of Tinea corporis •••••••••••• ••••• Treatment of Tinea cruris •••••••••••• ••• Treatment of Tinea cruris •••••••••••• ••••• Treatment of Tinea pedis •••••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
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 monooxygenase inhibitorHumans - Absorption
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
Not Available
- Protein binding
Not Available
- Metabolism
- 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.
- Half-life
Approximately 2 to 3 days following topical administration.
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- 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.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- 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 US Naftifine Hydrochloride Cream 1 mg/1g Topical Renaissance Pharma, Inc. 2016-10-01 2020-04-30 US Naftin Gel 10 mg/1g Topical Sebela Pharmaceuticals Inc. 2018-01-22 Not applicable US Naftin Cream 10 mg/2g Topical Merz Pharmaceuticals 2012-03-01 2016-12-01 US Naftin Cream 10 mg/1g Topical Physicians Total Care, Inc. 2010-06-17 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Naftifine Hydrochloride Gel 20 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2023-04-01 Not applicable US Naftifine Hydrochloride Cream 10 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2016-09-08 Not applicable US Naftifine Hydrochloride Gel 10 mg/1g Topical Amneal Pharmaceuticals of New York Llc 2019-03-20 Not applicable US Naftifine Hydrochloride Cream 20 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2016-01-06 Not applicable US Naftifine hydrochloride Cream 20 mg/1g Topical Xiromed, Llc 2021-01-15 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image EXODERIL CREAM 1 % Cream 1 % Topical NOVARTIS CORPORATION (MALAYSIA) SDN. BHD. 2022-01-11 Not applicable Malaysia EXODERIL CREAM 1 % Cream 1 % Topical NOVARTIS CORPORATION (MALAYSIA) SDN. BHD. 2020-09-08 2022-01-14 Malaysia Naftin Crm 1% Cream 1 % Topical Allergan Herbert Skin Care Division Of Allergan Inc. 1993-12-31 2011-08-04 Canada Naftin Gel 1% Gel 1 % Topical Allergan Herbert Skin Care Division Of Allergan Inc. 1993-12-31 2011-08-04 Canada
Categories
- ATC Codes
- D01AE22 — Naftifine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Naphthalenes
- Sub Class
- Not Available
- Direct Parent
- Naphthalenes
- Alternative Parents
- Styrenes / Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 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
Chemical Identifiers
- UNII
- 4FB1TON47A
- CAS number
- 65472-88-0
- InChI Key
- 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-yl)methyl](3-phenylprop-2-en-1-yl)amine
- SMILES
- CN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C12
References
- Synthesis Reference
- US4282251
- General References
- External Links
- KEGG Compound
- C08071
- PubChem Compound
- 73342
- PubChem Substance
- 46504777
- ChemSpider
- 43344
- BindingDB
- 50170647
- 31476
- ChEBI
- 7451
- ChEMBL
- CHEMBL626
- ZINC
- ZINC000001530977
- Therapeutic Targets Database
- DAP000752
- PharmGKB
- PA164748617
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Naftifine
- MSDS
- Download (14.2 KB)
Clinical Trials
- 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
Pharmacoeconomics
- Manufacturers
- Merz pharmaceuticals llc
- Packagers
- DPT Laboratories Ltd.
- Merz Pharmaceuticals LLC
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Gel Topical 2 % Cream Topical Gel Topical Solution Topical Spray Topical 1 % 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 % Cream Topical 10 MG/G Gel Topical 1 % Solution Topical 1 % Solution Topical 10 MG/ML - Prices
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 g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9161914 No 2015-10-20 2033-01-31 US US8778365 No 2014-07-15 2033-01-31 US US10166206 No 2019-01-01 2033-01-31 US US10166205 No 2019-01-01 2033-01-31 US US10695303 No 2020-06-30 2033-01-31 US US10729667 No 2020-08-04 2033-01-31 US
Properties
- State
- Solid
- 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) 8.99 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Squalene monooxygenase
- Molecular Weight
- 63922.505 Da
References
- 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 at June 13, 2005 13:24 / Updated at May 03, 2024 10:04