Amorolfine

Amorolfine
Systematic (IUPAC) name

(±)-(2R,6S)-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	78613-35-1^Y
ATC code	D01AE16 (WHO)
PubChem	CID 54260
ChemSpider	49010^Y
UNII	AB0BHP2FH0^Y
KEGG	D02923^Y
ChEBI	CHEBI:599440^Y
ChEMBL	CHEMBL489411^Y
Chemical data
Formula	C₂₁H₃₅NO
Molar mass	317.509 g/mol
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 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.^[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 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^‡ chlormidazole^‡ croconazole^‡ fenticonazole^‡ isoconazole^‡ luliconazole neticonazole^‡ omoconazole^‡ butoconazole clotrimazole^# econazole ketoconazole miconazole^# oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

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

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

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

Allylamines
(squalene monooxygenase
inhibitors)

Topical: amorolfine^‡
butenafine
naftifine
terbinafine
Systemic: terbinafine

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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