Basic information
- CAS
67467-83-8- Standard SMILES
CCC(C)(C)c1ccc(CC(C)CN2C[C@@H](C)O[C@@H](C)C2)cc1- InChIKey
MQHLMHIZUIDKOO-AYHJJNSGSA-N- Molecular formula
- C21H35NO
- Average molar mass
- 317.5 g/mol
- Monoisotopic mass
- 317.27186474
Overview
Amorolfine is a member of the class of morpholines that is cis-2,6-dimethylmorpholine in which the hydrogen attached to the nitrogen is replaced by a racemic 2-methyl-3-[p-(2-methylbutan-2-yl)phenyl]propyl group. An inhibitor of the action of squalene monooxygenase, 14 reductase and D7-D8 isomerase and an antifungal agent, it is used (generally as its hydrochloride salt) for the topical treatment of fungal nail and skin infections. It has a role as an EC 1.14.13.132 (squalene monooxygenase) inhibitor, an EC 1.3.1.70 (Delta(14)-sterol reductase) inhibitor and an EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor. It is a tertiary amino compound and a morpholine antifungal drug. It is a conjugate base of an amorolfine(1+).
Names & identifiers
- Preferred name
- Amorolfine
- IUPAC
- (2S,6R)-2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine
- English name
- Amorolfine
- Molecular formula
- C21H35NO
- Molecular weight
- 317.51
Names & synonyms
Amorolfine78613-35-1LocerylAmorolfinaAmorolfinumamorolfinCuranailLocetarOdenilRo 14-4767/000OmicurDTXSID0046690
Show more names
AmorofenAmorophen(+/-)-AmorolfineAmorolfine Impurity 19Amorolfine Impurity 22Voriconazole Impurity 97(2R,6S)-4-[3-(4-tert-amylphenyl)-2-methyl-propyl]-2,6-dimethyl-morpholinecis-4-[3-[4-(1,1-dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine
Amorolfine (as hydrochloride)(2R,6S)-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholineDTXCID8026690CHEBI:599440(2R,6S)-2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholineRo-14-4767/000Loceryl curanailRo-14-4767-002
Database identifiers
- CAS
67467-83-8、78613-35-1- PubChem CID
- 54260
- DTXSID
DTXSID0046690- ChEMBL
CHEMBL489411
Properties
Computed structural properties
- XLogP
- 5.7
- Topological polar surface area
- 12.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 336
Physicochemical properties
- Boiling point
- 407.1 · 407.1±33.0 °C(Predicted)
- Density
- 0.924 · 0.924±0.06 g/cm3(Predicted)
- storage temp.
- Refrigerator, under inert atmosphere
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Oil
- pka
- 7.33 · 7.33±0.10(Predicted)
- color
- Colourless
- FDA UNII
- 0 BHP2FH0 · AB0BHP2FH0
- ATC code
- 1 AE16 · D01AE16
Safety & regulation
Hazard information
Regulatory Information
Morpholine, 4-3-4-(1,1-dimethylpropyl)phenyl-2-methylpropyl-2,6-dimethyl-, (2R,6S)-rel-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Chemistry & industry
Pharmacology
ATC Code
D01AE16
D - Dermatologicals
QD - Dermatologicals
PharmacodynamicsAmorolfine is an antifungal agent with fungistatic and fungicidal activity in vitro.
Mechanism of Action
Amorolfine mediates its antifungal effects by interfering with ergosterol biosynthesis in the fungal cell membrane by inhibiting delta(14)-sterol reductase and cholestenol delta-isomerase. It alters the membrane sterol content, thereby changing the membrane permeability and disrupting metabolic processes.
MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >75
Applications
UsesAmorolfine is available for topical use in 0.25% cream and 5% nail lacquer formulation for the treatment of onychomycosis in European countries and Japan. However, amorolfine is not approved in the USA for such indications. The major advantage of this new antimycotic drug presumably lies in its potential for use as 5% nail lacquer in the treatment of onychomycosis caused by dermatophytes and Candida spp.
UsesAntimycotic.
UsesAmorolfine is a novel antifungal agent used in the treatment of cutaneous fungal disease.
Upstream & downstream products
Downstream products
Related reactions
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Compound notes
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