amorolfine

Also 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

In the Vinony graph

Vinony's link graph records 97 inbound references to amorolfine, and connects out to International Standard Book Number, digital object identifier and chemical formula.

Vinony files it under Antifungals, Chemical pages without DrugBank identifier and Morpholines.

Vinony links it to 16 Wikipedia language editions.

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 Å²
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

Sources (4)

via Wikidata · CC0

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Encyclopedic overview

1 sections

Contents

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 =

Excerpted from Wikipedia’s “amorolfine” article, available under the CC BY-SA 4.0 licence.