Amorolfine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Amorolfine
Accession Number
DB09056
Type
Small Molecule
Groups
Approved, Investigational
Description

Amorolfine (or amorolfin), is a morpholine antifungal drug that inhibits D14 reductase and D7-D8 isomerase, which depletes ergosterol and causes ignosterol to accumulate in the fungal cytoplasmic cell membranes. Marketed as Curanail, Loceryl, Locetar, and Odenil, amorolfine is commonly available in the form of a nail lacquer, containing 5% amorolfine as the active ingredient. It is used to treat onychomycosis (fungal infection of the toe- and fingernails). Amorolfine 5% nail lacquer in once-weekly or twice-weekly applications has been shown in two studies to be between 60% and 71% effective in treating toenail onychomycosis; complete cure rates three months after stopping treatment (after six months of treatment) were 38% and 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, but can be ordered from there by mail from other countries.

Structure
Thumb
Synonyms
  • Amorolfin
External IDs
RO 14-4767/000 / RO-14-4767/000
International/Other Brands
Curanail / Loceryl / Locetar / Odenil
Categories
UNII
AB0BHP2FH0
CAS number
78613-35-1
Weight
Average: 317.517
Monoisotopic: 317.271864751
Chemical Formula
C21H35NO
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcenocoumarolAmorolfine may increase the anticoagulant activities of Acenocoumarol.
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Amorolfine.
AmrinoneThe therapeutic efficacy of Amorolfine can be increased when used in combination with Amrinone.
AzimilideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Azimilide.
BuspironeThe metabolism of Buspirone can be decreased when combined with Amorolfine.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Amorolfine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Amorolfine.
DidanosineDidanosine can cause a decrease in the absorption of Amorolfine resulting in a reduced serum concentration and potentially a decrease in efficacy.
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Amorolfine.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Amorolfine.
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
49010
ChEBI
599440
ChEMBL
CHEMBL489411
Wikipedia
Amorolfine
ATC Codes
D01AE16 — Amorolfine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentOnychomycosis1
3Active Not RecruitingTreatmentOnychomycosis1
3CompletedTreatmentOnychomycosis1
4CompletedTreatmentOnychomycosis1
4RecruitingTreatmentNon-dermatophyte Onychomycosis1
4Unknown StatusTreatmentOnychomycosis1
Not AvailableCompletedTreatmentOnychomycosis1
Not AvailableCompletedTreatmentOnychomycosis of Toenail1
Not AvailableUnknown StatusTreatmentOnycomycosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
Phenylpropane / Aralkylamine / Morpholine / Oxazinane / Tertiary amine / Tertiary aliphatic amine / Organoheterocyclic compound / Ether / Dialkyl ether / Azacycle
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary amino compound, morpholine antifungal drug (CHEBI:599440)

Drug created on May 11, 2015 12:00 / Updated on August 02, 2018 06:13