Amorolfine hydrochlorideProduct ingredient for Amorolfine
- Name
- Amorolfine hydrochloride
- Drug Entry
- Amorolfine
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.
- Accession Number
- DBSALT002882
- Structure
- Synonyms
- Amorolfine HCl / Amorolfine hydrochloride
- UNII
- 741YH7379H
- CAS Number
- 78613-38-4
- Weight
- Average: 353.98
Monoisotopic: 353.2485425 - Chemical Formula
- C21H36ClNO
- InChI Key
- XZKWIPVTHGWDCF-KUZYQSSXSA-N
- InChI
- InChI=1S/C21H35NO.ClH/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;1H/t16?,17-,18+;
- IUPAC Name
- (2R,6S)-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine hydrochloride
- SMILES
- Cl.[H]C(C)(CN1C[C@]([H])(C)O[C@]([H])(C)C1)CC1=CC=C(C=C1)C(C)(C)CC
- External Links
- Predicted Properties
Property Value Source Water Solubility 0.000785 mg/mL ALOGPS logP 5.44 ALOGPS logP 5.62 Chemaxon logS -5.6 ALOGPS pKa (Strongest Basic) 8.49 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 99.61 m3·mol-1 Chemaxon Polarizability 40.23 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon