Amorolfine

HCID 54260CAS 67467-83-8
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Grundinformationen

Standard-SMILES
CCC(C)(C)c1ccc(CC(C)CN2C[C@@H](C)O[C@@H](C)C2)cc1
InChIKey
MQHLMHIZUIDKOO-AYHJJNSGSA-N
Summenformel
C21H35NO
Durchschnittliche Molmasse
317,5 g/mol
Monoisotopische Masse
317,27186474

Überblick

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+).

Namen und Bezeichner

Bevorzugter Name
Amorolfine
IUPAC
(2S,6R)-2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine

Namen und Synonyme

Amorolfine78613-35-1LocerylAmorolfinaAmorolfinumamorolfinCuranailLocetarOdenilRo 14-4767/000OmicurDTXSID0046690
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
67467-83-8、78613-35-1
PubChem CID
54260
DTXSID
DTXSID0046690
ChEMBL
CHEMBL489411
ChEBI
CHEBI:599440
Nikkaji
J389.118F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,7
Polarare Oberfläche (TPSA)
12,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
6
Schwere Atome
23

Sicherheit und Regulatorisches

Gefahrenhinweise

Regulatory Information · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

D01AE16

D - Dermatologicals

QD - Dermatologicals

PharmacodynamicsAmorolfine is an antifungal agent with fungistatic and fungicidal activity in vitro.
Mechanism of Action · 1 Eintrag

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.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >75

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