Amorolfine

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
Thumb
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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Medicalerrors
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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.
DrugInteraction
AcenocoumarolAmorolfine may increase the anticoagulant activities of Acenocoumarol.
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Food Interactions
Not Available

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Amorolfine hydrochloride741YH7379H78613-38-4XZKWIPVTHGWDCF-KUZYQSSXSA-N
International/Other Brands
Curanail / Loceryl / Locetar / Odenil
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LOCERYL NAIL LACQUER 5% SOLUTIONSolutionTopicalZUELLIG PHARMA SDN BHD2020-09-08Not applicableMalaysia flag
Mycofine 5% w/v Nail LacquerSolutionTopicalPAHANG PHARMACY SDN. BHD.2020-09-08Not applicableMalaysia flag

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
ChemSpider
49010
RxNav
17804
ChEBI
599440
ChEMBL
CHEMBL489411
Wikipedia
Amorolfine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentFoot Dermatoses3
4CompletedTreatmentNon-dermatophyte Onychomycosis1
4CompletedTreatmentOnychomycosis1
4Unknown StatusTreatmentOnychomycosis1
3CompletedTreatmentOnychomycosis2
2Unknown StatusTreatmentOnychomycosis1
Not AvailableCompletedTreatmentOnychomycosis1
Not AvailableCompletedTreatmentOnychomycosis of Toenail1
Not AvailableUnknown StatusTreatmentOnychomycosis of Toenail1
Not AvailableUnknown StatusTreatmentOnycomycosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionTopical
SolutionCutaneous
SolutionTopical5 g
CreamTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000785 mg/mLALOGPS
logP5.44ALOGPS
logP5.62ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.61 m3·mol-1ChemAxon
Polarizability40.23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on May 11, 2015 18:00 / Updated on May 27, 2021 02:57