Luliconazole
Identification
- Name
- Luliconazole
- Accession Number
- DB08933
- Description
Luliconazole is a topical antifungal agent that acts by unknown mechanisms but is postulated to involve altering the synthesis of fungi cell membranes. It was approved by the FDA (USA) in November 2013 and is marketed under the brand name Luzu. Luliconazole is also approved in Japan.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Luliconazole (DB08933)
- Weight
- Average: 354.27
Monoisotopic: 352.961495 - Chemical Formula
- C14H9Cl2N3S2
- Synonyms
- Luliconazole
- External IDs
- NND-502
- PR-2699
Pharmacology
- Indication
Luliconazole is indicated in adults aged 18 years and older for the topical treatment of fungal infections caused by Trichophyton rubrum and Epidermophyton floccosum, specifically tinea pedis, cruris, and corporis.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Luliconazole kills the organisms Trichophyton rubrum and Epidermophyton floccosum, most likely by altering their fungal cell membranes.
- Mechanism of action
The exact mechanism of action for luliconazole's anti-fungal activity is still not known, but luliconazole is thought to inhibit the enzyme lanosterol demethylase. Lanosterol demethylase is needed for the synthesis of ergosterol, which is a major component of the fungus cell membranes.
Target Actions Organism ACytochrome P450 51 inhibitorYeast - Absorption
Although luliconazole is administered topically, clinical studies have shown that after the first dose in patients with tina pedis, a maximum plasma concentration of 0.40 ± 0.76 ng/mL (mean ± SD) occurred in 16.9 ± 9.39 hours (mean ± SD).
- Volume of distribution
The volume of distribution was not quantified.
- Protein binding
Plasma protein binding of luliconazole is >99%.
- Metabolism
The metabolism of luliconazole has yet to be determined.
- Route of elimination
The route of elimination of luliconazole has yet to be determined.
- Half-life
The half life of luliconazole has yet to be determined.
- Clearance
The clearance of luliconazole has yet to be determined.
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
In clinical trials, no serious toxicity was reported, only local irritation (mild contact dermatitis and cellulitis) at the site of application was found.
- Affected organisms
- Fungi
- 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.
Drug Interaction Unlock Additional DataAcenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Luliconazole. Albendazole The serum concentration of Albendazole can be increased when it is combined with Luliconazole. Amitriptyline The serum concentration of Amitriptyline can be increased when it is combined with Luliconazole. Apixaban The serum concentration of Apixaban can be increased when it is combined with Luliconazole. Artemether The serum concentration of Artemether can be increased when it is combined with Luliconazole. Axitinib The serum concentration of Axitinib can be increased when it is combined with Luliconazole. Carisoprodol The serum concentration of Carisoprodol can be increased when it is combined with Luliconazole. Cenobamate The serum concentration of Cenobamate can be increased when it is combined with Luliconazole. Citalopram The serum concentration of Citalopram can be increased when it is combined with Luliconazole. Clobazam The serum concentration of Clobazam can be increased when it is combined with Luliconazole. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- No interactions found.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- International/Other Brands
- Lulicon (Pola Pharma )
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataLuliconazole Cream 10 mg/1g Topical Oceanside Pharmaceuticals 2018-06-15 Not applicable US 
Luzu Cream 10 mg/1g Topical Bausch Health US, LLC 2013-11-14 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories
- ATC Codes
- D01AC18 — Luliconazole
- Drug Categories
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Azole Antifungals
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Imidazole and Triazole Derivatives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Dichlorobenzenes
- Alternative Parents
- N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / 1,3-dithiolanes / Nitriles / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,3-dichlorobenzene / 1,3-dithiolane / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Carbonitrile / Dithiolane / Heteroaromatic compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- dichlorobenzene (CHEBI:34825)
Chemical Identifiers
- UNII
- RE91AN4S8G
- CAS number
- 187164-19-8
- InChI Key
- YTAOBBFIOAEMLL-REQDGWNSSA-N
- InChI
- InChI=1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1
- IUPAC Name
- 2-[(2E,4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile
- SMILES
- ClC1=CC(Cl)=C(C=C1)[[email protected]@H]1CS\C(S1)=C(\C#N)N1C=CN=C1
References
- Synthesis Reference
Niwano Y, Kuzuhara N, Kodama H, Yoshida M, Miyazaki T, Yamaguchi H: In vitro and in vivo antidermatophyte activities of NND-502, a novel optically active imidazole antimycotic agent. Antimicrob Agents Chemother. 1998 Apr;42(4):967-70.
- General References
- Niwano Y, Kuzuhara N, Kodama H, Yoshida M, Miyazaki T, Yamaguchi H: In vitro and in vivo antidermatophyte activities of NND-502, a novel optically active imidazole antimycotic agent. Antimicrob Agents Chemother. 1998 Apr;42(4):967-70. [PubMed:9559824]
- Uchida K, Nishiyama Y, Yamaguchi H: In vitro antifungal activity of luliconazole (NND-502), a novel imidazole antifungal agent. J Infect Chemother. 2004 Aug;10(4):216-9. [PubMed:15365862]
- External Links
- KEGG Drug
- D01980
- KEGG Compound
- C13478
- PubChem Compound
- 3003141
- PubChem Substance
- 175427163
- ChemSpider
- 2273807
- 1482680
- ChEBI
- 34825
- ChEMBL
- CHEMBL2105689
- ZINC
- ZINC000003929486
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Luliconazole
- FDA label
- Download (199 KB)
- MSDS
- Download (567 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Tinea Corporis 1 4 Completed Treatment Tinea Cruris / Tinea Pedis 2 4 Not Yet Recruiting Treatment Tinea infections 1 2 Completed Treatment Tinea Pedis 1 2, 3 Completed Treatment Distal and Lateral Subungual Onychomycosis 1 1, 2 Completed Treatment Onychomycosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 10 mg/1g - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5900488 No 1999-05-04 2016-07-05 US US9012484 No 2015-04-21 2033-09-06 US US8980931 No 2015-03-17 2034-04-28 US US9199977 No 2015-12-01 2033-09-06 US US9453006 No 2016-09-27 2033-09-06 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
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Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0659 mg/mL ALOGPS logP 4.27 ALOGPS logP 4.07 ChemAxon logS -3.7 ALOGPS pKa (Strongest Basic) 6.34 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 41.61 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 101 m3·mol-1 ChemAxon Polarizability 33.65 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Niwano Y, Koga H, Kodama H, Kanai K, Miyazaki T, Yamaguchi H: Inhibition of sterol 14 alpha-demethylation of Candida albicans with NND-502, a novel optically active imidazole antimycotic agent. Med Mycol. 1999 Oct;37(5):351-5. [PubMed:10520160]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- 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
- luliconazole - Drug Summary PDR [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
Drug created on December 29, 2013 15:57 / Updated on June 12, 2020 11:42
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