Amorolfine

HCID 54260
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基本情報

CAS
67467-83-8
標準SMILES
CCC(C)(C)c1ccc(CC(C)CN2C[C@@H](C)O[C@@H](C)C2)cc1
InChIKey
MQHLMHIZUIDKOO-AYHJJNSGSA-N
分子式
C21H35NO
平均分子量
317.5 g/mol
単同位体質量
317.27186474

概要

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+).

名称と識別子

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

名称と別名

Amorolfine78613-35-1LocerylAmorolfinaAmorolfinumamorolfinCuranailLocetarOdenilRo 14-4767/000OmicurDTXSID0046690
名称をさらに表示
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

データベース識別子

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

物性

構造計算による物性補完中

XLogP
5.7
極性表面積
12.5 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
6
重原子数
23

安全と法規制

危険有害性情報

Regulatory Information · 1 件

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.

化学と産業

薬理情報

ATC Code · 3 件

D01AE16

D - Dermatologicals

QD - Dermatologicals

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

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.

用途と製造

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

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