Amorolfine

Amorolfine
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	D01AE16 (WHO)
Identifiers
IUPAC name (±)-(2R,6S)-rel-2,6-Dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine
CAS Number	78613-35-1^Y
PubChem (CID)	54260
ChemSpider	49010^Y
UNII	AB0BHP2FH0^Y
KEGG	D02923^Y
ChEBI	CHEBI:599440^Y
ChEMBL	CHEMBL489411^Y
Chemical and physical data
Formula	C₂₁H₃₅NO
Molar mass	317.509 g/mol
3D model (Jmol)	Interactive image
SMILES O2[C@@H](CN(CC(C)Cc1ccc(cc1)C(C)(C)CC)C[C@@H]2C)C
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+^Y Key:MQHLMHIZUIDKOO-AYHJJNSGSA-N^Y
(verify)

Amorolfine (or amorolfin), is a morpholine antifungal drug that inhibits Δ¹⁴-sterol reductase and cholestenol Δ-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 hydrochloride 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.^[1]

It is a topical solution for the treatment of toenail infections. Systemic treatments may be considered more effective.^[1]

It is approved for sale over-the-counter in Australia, Russia 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.^[2]

Notes

1 2 Hywel C. Williams (2003). Evidence-Based Dermatology. Blackwell.
↑ It can readily be verified that Curanail is advertised on websites such as US Amazon.com, shipped from abroad.

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ clotrimazole^# croconazole^‡ econazole fenticonazole^‡ flutrimazole isoconazole^‡ ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

Triazoles	Topical: efinaconazole fluconazole^# fosfluconazole terconazole Systemic: fluconazole^# hexaconazole^‡ isavuconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡ ravuconazole^†

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine

Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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