This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Summary
Amorolfine is a morpholine derivative commonly applied as a lacquer for onychomycosis but is also used for superficial dermatomycosis.
- Generic Name
- Amorolfine
- DrugBank Accession Number
- DB09056
- Background
Amorolfine or amorolfin, is a morpholine antifungal drug that inhibits the fungal enzymes D14 reductase and D7-D8 isomerase. This inhibition affects fungal sterol synthesis pathways, depleting ergosterol and causing ignosterol to accumulate in the fungal cytoplasmic cell membranes. Amorolfine is marketed as Curanail, Loceryl, Locetar, and Odenil. It is available in the form of a 5% amorolfine nail lacquer used to treat onychomycosis (fungal infection of the toe- and fingernails). Amorolfine 5% nail lacquer in once or twice weekly applications is 60-71% effective in treating toenail onychomycosis; complete cure rates three months after stopping treatment (after six months of treatment) were 38-46%. However, full experimental details of these trials were not available and since they were first reported in 1992 there have been no subsequent trials.
It is a topical solution for the treatment of toenail infections. Systemic treatments may be considered more effective.
It is approved for sale over the counter in Australia and the UK (recently re-classified to over the counter status), and is approved for the treatment of toenail fungus by prescription in other countries. It is not approved for the treatment of onychomycosis in the United States or Canada.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Amorolfine (DB09056)
- Weight
- Average: 317.517
Monoisotopic: 317.271864751 - Chemical Formula
- C21H35NO
- Synonyms
- Amorolfin
- Amorolfina
- Amorolfine
- External IDs
- RO 14-4767/000
- RO-14-4767/000
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Candidiasis, cutaneous ••• ••• ••••• Treatment of Dermatomycoses ••• ••• ••••• Treatment of Fungus, nail ••• ••• •••••••• Treatment of Pityriasis versicolor ••• ••• ••••• Treatment of Tinea corporis ••• ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol Amorolfine may increase the anticoagulant activities of Acenocoumarol. - Food Interactions
- Not Available
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 Amorolfine hydrochloride 741YH7379H 78613-38-4 XZKWIPVTHGWDCF-KUZYQSSXSA-N - International/Other Brands
- Curanail / Loceryl / Locetar / Odenil
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image AMOROLFINE NAIL LACQUER 5%W/V Solution 50.00 mg/ml Cutaneous MEDICELL PHARMACEUTICAL (S) PTE. LTD. 2014-05-09 Not applicable Singapore 
LOCERYL NAIL LACQUER 5% Solution 5 % w/v Topical GALDERMA SINGAPORE PRIVATE LIMITED 1993-09-28 Not applicable Singapore LOCERYL NAIL LACQUER 5% SOLUTION Solution Topical ZUELLIG PHARMA SDN BHD 2020-09-08 Not applicable Malaysia 
Mycofine 5% w/v Nail Lacquer Solution Topical PAHANG PHARMACY SDN. BHD. 2020-09-08 Not applicable Malaysia
Categories
- ATC Codes
- D01AE16 — Amorolfine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylpropanes
- Direct Parent
- Phenylpropanes
- Alternative Parents
- Aralkylamines / Morpholines / Trialkylamines / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Dialkyl ether / Ether / Hydrocarbon derivative / Morpholine / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary amino compound, morpholine antifungal drug (CHEBI:599440)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- AB0BHP2FH0
- CAS number
- 78613-35-1
- InChI Key
- MQHLMHIZUIDKOO-AYHJJNSGSA-N
- InChI
- InChI=1S/C21H35NO/c1-7-21(5,6)20-10-8-19(9-11-20)12-16(2)13-22-14-17(3)23-18(4)15-22/h8-11,16-18H,7,12-15H2,1-6H3/t16?,17-,18+
- IUPAC Name
- (2R,6S)-2,6-dimethyl-4-(2-{[4-(2-methylbutan-2-yl)phenyl]methyl}propyl)morpholine
- SMILES
- [H]C(C)(CN1C[C@]([H])(C)O[C@]([H])(C)C1)CC1=CC=C(C=C1)C(C)(C)CC
References
- General References
- Not Available
- External Links
- ChemSpider
- 49010
- 17804
- ChEBI
- 599440
- ChEMBL
- CHEMBL489411
- Wikipedia
- Amorolfine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Foot Dermatoses 3 4 Completed Treatment Non-dermatophyte Onychomycosis 1 4 Completed Treatment Onychomycosis 1 4 Unknown Status Treatment Onychomycosis 1 3 Completed Treatment Onychomycosis 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Topical Solution Cutaneous 50.00 mg/ml Solution Topical 5 g Solution Topical 50 MG/ML Cream Cutaneous 0.250 g Solution Cutaneous 5 % Solution Topical 5 % w/v Cream Topical 0.25 % Solution Topical 5 % Solution Topical 50.00 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000785 mg/mL ALOGPS logP 5.44 ALOGPS logP 5.62 Chemaxon logS -5.6 ALOGPS pKa (Strongest Basic) 8.49 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 99.61 m3·mol-1 Chemaxon Polarizability 40.23 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes 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 splash10-014i-1598000000-6d2533cd40c830253232 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0019000000-d2a0930cb37dc388bbe4 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0759000000-3f5c1e1fb3a85487305f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03xr-3493000000-39cf83efba1eddd279d3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0i0s-2932000000-64c5833aca88f353833d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ab9-5951000000-f28295bd27c33142afa4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 204.6302507 predictedDarkChem Lite v0.1.0 [M-H]- 185.95427 predictedDeepCCS 1.0 (2019) [M+H]+ 204.8359507 predictedDarkChem Lite v0.1.0 [M+H]+ 188.34984 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.0350507 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.26237 predictedDeepCCS 1.0 (2019)
Drug created at May 11, 2015 18:00 / Updated at May 27, 2021 02:57