AMOROLFINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H35NO
Molecular Weight	317.5087
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(C)(C)C1=CC=C(C[C@H](C)CN2C[C@H](C)O[C@H](C)C2)C=C1

InChI

InChIKey=MQHLMHIZUIDKOO-OKZBNKHCSA-N

InChI=1S/C21H35NO/c1-7-21(5,6)20-10-8-19(9-11-20)12-16(2)13-22-14-17(3)23-18(4)15-22/h8-11,16-18H,7,12-15H2,1-6H3/t16-,17-,18+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H35NO
Molecular Weight	317.5087
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con213151.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/uk/loceryl-nail-lacquer-5-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/1458670 | https://www.medicines.org.uk/emcmobile/PIL.14805.latest.pdf

Amorolfine (or amorolfin), is a morpholine antifungal drug with broad spectrum of activity. Its fungicidal action is based on an alteration of the fungal cell membrane targeted primarily on sterol biosynthesis. Amorolfine is administered as a nail lacquer in patients suffering from onychomycosis, as a cream in patients suffering from dermatomycosis. Amorolfine is well tolerated. The local adverse effects observed were mainly burning and itching.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Delta(14)-sterol reductase 2 Target ID: P32462 Gene ID: 855441.0 Gene Symbol: ERG24 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1458670 \| https://www.ncbi.nlm.nih.gov/pubmed/3328047	Inhibitor 8297		2.93 µM [IC50]
Δ7-cholestenol Δ7-Δ8-isomerase (fungi) 2 Target ID: Δ7-cholestenol Δ7-Δ8-isomerase (fungi) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1458670	Inhibitor 8297		1.8 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Onychomycosis 18 Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/LOCERYL-ALONZARCHAN-ENG-08-2015_1439719917883.pdf	Curative		Approved 8429	Loceryl Approved Use The medicine is intended for the treatment of nails infected with different types of fungus. Launch Date 1991
Dermatomycosis 20 Sources: http://www.vademecum.es/medicamento-locetar_prospecto_60559	Curative		Approved 8429	Loceryl Approved Use The cream is intended for the treatment of dermatomycosis with different types of fungus. Launch Date 1991

PubMed

Title	Date	PubMed
Synergy between 6-amino-2-n-pentylthiobenzothiazole and ergosterol biosynthesis-inhibiting antimycotics against Candida albicans in vitro.	2000 Jul	10854813
[The treatment of extensive onychomycosis in aged patients].	2001	16886433
Topical amorolfine for 15 months combined with 12 weeks of oral terbinafine, a cost-effective treatment for onychomycosis.	2001 Oct	11777260
The KEX2 gene of Candida glabrata is required for cell surface integrity.	2001 Sep	11580846
Best foot forward.	2001 Sep 5-11	12206056
'Deep' white superficial onychomycosis due to molds.	2002 Sep	12428856
[Dual therapy of onychomycoses. Only Schwaben Province physicians also think of costs].	2003 Oct 9	14655472
Pharmacoeconomic issues in onychomycosis.	2003 Sep	14510972
Actin gene-targeted RT-PCR could be a useful method for evaluating in vitro fungicidal activity against dermatophytes.	2003 Sep-Oct	14587308
A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers.	2004	15573688
Testing of antifungal combinations against yeasts and dermatophytes.	2004 Apr	15204161
Evaluation of the drug treatment and persistence of onychomycosis.	2004 Aug 31	15349516
[Onychomycosis].	2004 Feb	14968324
Onychomycosis in children: a brief overview with treatment strategies.	2004 Jan-Feb	14871333
Combination treatment of candidal fingernail onychomycosis.	2004 Jun	15214929
Treatment costs of three nail lacquers used in onychomycosis.	2005	16428149
Pharmacotherapy of onychomycosis.	2005 Apr	15934887
Topical antifungal drugs for the treatment of onychomycosis: an overview of current strategies for monotherapy and combination therapy.	2005 Jan	15649187
Candida-related denture stomatitis: a pilot study of the efficacy of an amorolfine antifungal varnish.	2005 Jan-Feb	15754893
In vitro susceptibility of 15 strains of zygomycetes to nine antifungal agents as determined by the NCCLS M38-A microdilution method.	2005 Jul	15982206
Treatment options--development of consensus guidelines.	2005 Sep	16120203
Topical treatments for fungal infections of the skin and nails of the foot.	2007 Jul 18	17636672
Update in antifungal therapy of dermatophytosis.	2008 Nov-Dec	18478357
Toenail onychomycosis in diabetic patients: issues and management.	2009	19489654
[Fungicidal activity of liranaftate against dermatophytes].	2009	19194054
Update on terbinafine with a focus on dermatophytoses.	2009 Apr 21	21436968
Fungal nail infections: diagnosis and management.	2009 Feb	19391293
Preventing long term relapsing tinea unguium with topical anti-fungal cream: a case report.	2009 Jan 21	19154619
Efficacy of amorolfine nail lacquer for the prophylaxis of onychomycosis over 3 years.	2010 Aug	20028447
Chemical combinations elucidate pathway interactions and regulation relevant to Hepatitis C replication.	2010 Jun 8	20531405

Patents

Sample Use Guides

In Vivo Use Guide

The lacquer is applied once to twice a week

Route of Administration: Topical

In Vitro Use Guide

The dermatophytes, dematiaceous fungi, dimorphic fungi and yeasts were generally inhibited by less than 1 mg/ml of Amorolfine. At concentration 3-10 mg/ml Amorolfine kills more than 90% of the Candida albicans, Histoplasma capsulatum, Wangiella dermatitidis and Trichophyton mentagrophytes within 24 h incubation on casitone medium.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:54:50 GMT 2023` Edited by `admin` on `Sat Dec 16 15:54:50 GMT 2023`
Record UNII	AB0BHP2FH0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMOROLFINE

Official Name

English

amorolfine [INN]

Common Name

English

(±)-CIS-2,6-DIMETHYL-4-(2-METHYL-3-(P-TERT-PENTYLPHENYL)PROPYL)MORPHOLINE

Common Name

English

MORPHOLINE, 4-(3-(4-(1,1-DIMETHYLPROPYL)PHENYL)-2-METHYLPROPYL)-2,6-DIMETHYL-, CIS-, (±)-

Systematic Name

English

LOCERYL

Brand Name

English

AMOROLFINE [USAN]

Common Name

English

Amorolfine [WHO-DD]

Common Name

English

RO 14-4767/000

Code

English

AMOROLFINE [MART.]

Common Name

English

AMOROLFINE [MI]

Common Name

English

RO-14-4767/000

Code

English

Classification Tree Code System Code

WHO-ATC

D01AE16