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
DrugInteractionDrug group
AcenocoumarolAmorolfine may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AgmatineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Amorolfine can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Amorolfine.Approved, Investigational
AmrinoneThe therapeutic efficacy of Amorolfine can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Aranidipine.Approved, Investigational
AzelnidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Amorolfine can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Amorolfine can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Amorolfine can be increased when used in combination with Bioallethrin.Approved, Experimental
BuspironeThe metabolism of Buspirone can be decreased when combined with Amorolfine.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Amorolfine.Approved, Investigational
CarboxyamidotriazoleThe therapeutic efficacy of Amorolfine can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Amorolfine.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Amorolfine can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Amorolfine.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Amorolfine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe therapeutic efficacy of Amorolfine can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Amorolfine.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Amorolfine.Approved, Investigational
DotarizineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Amorolfine can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Amorolfine.Approved
FelodipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Amorolfine can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Amorolfine can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Amorolfine can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Amorolfine can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Amorolfine can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Amorolfine can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Amorolfine.Approved
Magnesium sulfateThe therapeutic efficacy of Amorolfine can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Amorolfine can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Methsuximide.Approved
MibefradilThe therapeutic efficacy of Amorolfine can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Amorolfine can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Amorolfine can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Amorolfine can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Amorolfine.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Amorolfine can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Amorolfine.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Amorolfine.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Amorolfine.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Amorolfine.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Amorolfine.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Amorolfine.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Amorolfine.Approved, Investigational
SeletracetamThe therapeutic efficacy of Amorolfine can be increased when used in combination with Seletracetam.Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Amorolfine.Approved
SucralfateSucralfate can cause a decrease in the absorption of Amorolfine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Amorolfine.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Amorolfine.Approved, Investigational
TerodilineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Amorolfine can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Amorolfine can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Amorolfine can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Amorolfine can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Amorolfine can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Amorolfine.Approved
ZonisamideThe therapeutic efficacy of Amorolfine can be increased when used in combination with Zonisamide.Approved, Investigational
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 June 02, 2018 08:15