Structure via PubChem · Public domain (PubChem)
amorolfine
Sign in to saveAlso known as meso-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine, meso-2,6-dimethyl-4-(2-methyl-3-(p-tert-pentylphenyl)propyl)morpholine, (+-)-cis-2,6-dimethyl-4-(2-methyl-3-(p-tert-pentylphenyl)propyl)morpholine
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. Sold under the brand name Loceryl among others, 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 was shown in two decades-old studies to be
Key facts
- Drug.image
- Amorolfine.svg
- Drug.image_class
- skin-invert-image
- Drug.caption
- Above: molecular structure of amorolfine Below: 3D representation of an amorolfine molecule
- Drug.image2
- Amorolfine 3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Loceryl, others
- Drug.ATC_prefix
- D01
- Drug.ATC_suffix
- AE16
- Drug.legal_AU
- S4
- Drug.legal_AU_comment
- /Schedule 2
- Drug.CAS_number
- 78613-35-1
- Drug.PubChem
- 54260
- Drug.ChemSpiderID
- 49010
- Drug.UNII
- AB0BHP2FH0
- Drug.KEGG
- D02923
- Drug.ChEBI
- 599440
- Drug.ChEMBL
- 489411
- Drug.IUPAC_name
- (±)-(2R,6S)-rel-2,6-Dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine
via Wikipedia infobox
Chemical data
- Formula
- C21H35NO
- Molecular weight
- 317.5 g/mol
- IUPAC name
- (2S,6R)-2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine
- SMILES
- CCC(C)(C)C1=CC=C(C=C1)CC(C)CN2C[C@H](O[C@H](C2)C)C
- InChIKey
- MQHLMHIZUIDKOO-AYHJJNSGSA-N
- XLogP
- 5.7
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- tinea unguium
via ChEMBL · EBI
Research
364 papers- Amorolfine vs. ciclopirox - lacquers for the treatment of onychomycosis.Postepy dermatologii i alergologii · 2015
- Onychomycosis: a review.Journal of the European Academy of Dermatology and Venereology : JEADV · 2020
- Tinea pedis: an updated review.Drugs in context · 2023
- Amorolfine. A review of its pharmacological properties and therapeutic potential in the treatment of onychomycosis and other superficial fungal infections.Drugs · 1995
- Onychomycosis.Clinics in dermatology · 2010
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 317.272
Show 7 more facts
- chemical formula
- C₂₁H₃₅NO
- subject has role
- antifungal
- Commons category
- Amorolfine
- canonical SMILES
- CCC(C)(C)C1=CC=C(C=C1)CC(C)CN2CC(OC(C2)C)C
- isomeric SMILES
- CCC(C)(C)C1=CC=C(C=C1)CC(C)CN2C[C@H](O[C@H](C2)C)C
- World Health Organisation international non-proprietary name
- amorolfine
- medical condition treated
- dermatomycosis
via Wikidata · CC0
~3 min read
Encyclopedic overview
1 sectionsContents
- Notes
{{Infobox drug | image = Amorolfine.svg | image_class = skin-invert-image | alt = | caption = Above: molecular structure of amorolfine Below: 3D representation of an amorolfine molecule | image2 = Amorolfine 3D.png | image_class2 = bg-transparent | alt2 =
| pronounce = | tradename = Loceryl, others | Drugs.com = | MedlinePlus = | DailyMedID = | pregnancy_AU = | pregnancy_AU_comment = | routes_of_administration = | class = | ATC_prefix = D01 | ATC_suffix = AE16 | ATC_supplemental =
Excerpted from Wikipedia’s “amorolfine” article, available under the CC BY-SA 4.0 licence.