AMOROLFINE

Possibly Marketed Outside US

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 8504		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 8504		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 8583	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 8583	Loceryl Approved Use The cream is intended for the treatment of dermatomycosis with different types of fungus. Launch Date 1991

PubMed

Title	Date	PubMed
Efficacy of amorolfine nail lacquer for the prophylaxis of onychomycosis over 3 years.	2010-08	20028447
Chemical combinations elucidate pathway interactions and regulation relevant to Hepatitis C replication.	2010-06-08	20531405
Effect of a novel penetration enhancer on the ungual permeation of two antifungal agents.	2010-06	20636860
[Allergic contact dermatitis due to amorolfine in nail lacquer].	2010-04	20398612
Onychomycosis.	2010-03-04	20347657
Long-term follow-up of toenail onychomycosis caused by dermatophytes after successful treatment with systemic antifungal agents.	2010-03	20159308
Hydrosoluble medicated nail lacquers: in vitro drug permeation and corresponding antimycotic activity.	2010-02-01	19886884
Onychomycosis insensitive to systemic terbinafine and azole treatments reveals non-dermatophyte moulds as infectious agents.	2010	20110639
Susceptibility testing of amorolfine, bifonazole and ciclopiroxolamine against Trichophyton rubrum in an in vitro model of dermatophyte nail infection.	2009-11	19888808
Onychomycosis and diabetes.	2009-10	19309423
Update on terbinafine with a focus on dermatophytoses.	2009-04-21	21436968
Rapid detection of dermatophytes from skin and hair.	2009-04-18	19374765
Fungal nail infections: diagnosis and management.	2009-02	19391293
Preventing long term relapsing tinea unguium with topical anti-fungal cream: a case report.	2009-01-21	19154619
[Guidelines for diagnosis and treatment of mucocutaneous candidiasis].	2009	19942790
Toenail onychomycosis in diabetic patients: issues and management.	2009	19489654
[Fungicidal activity of liranaftate against dermatophytes].	2009	19194054
In vitro antifungal activities of luliconazole, a new topical imidazole.	2009	19115136
Fungal toenail infections.	2008-12-15	19445781
Tinea capitis due to Trichophyton soudanense with a papular IDE reaction in Northern Italy.	2008-12	19169215
Treatment of onychomycosis: an update.	2008-11	21369429
Pooling overdispersed binomial data to estimate event rate.	2008-08-19	18713448
In vitro antifungal activity of sertaconazole nitrate against recent isolates of onychomycosis causative agents.	2008-08	18676237
Review of antifungal therapy and the severity index for assessing onychomycosis: part I.	2008	18484426
An open randomized comparative study to test the efficacy and safety of oral terbinafine pulse as a monotherapy and in combination with topical ciclopirox olamine 8% or topical amorolfine hydrochloride 5% in the treatment of onychomycosis.	2007-11-23	18032857
Update in antifungal therapy of dermatophytosis.	2007-10-15	18478357
1-Phenylethynylpyrene (1-PEPy) as refined excimer forming alternative to pyrene: case of DNA major groove excimer.	2007-09-28	17896811
Topical treatments for fungal infections of the skin and nails of the foot.	2007-07-18	17636672
A multicentre, randomized, controlled study of the efficacy, safety and cost-effectiveness of a combination therapy with amorolfine nail lacquer and oral terbinafine compared with oral terbinafine alone for the treatment of onychomycosis with matrix involvement.	2007-07	17553051
Toenail onychomycosis: current and future treatment options.	2007-04-04	17403258
Onychomycosis in the elderly : drug treatment options.	2007	17432924
Sublimation of antimycotic agents as proved by various analytical methods.	2006-12	17283666
Rapid response of distal subungual onychomycosis to 5% amorolfine nail lacquer in a 20-month-old healthy infant.	2006-08-22	16918646
Different physicochemical properties of antimycotic agents are relevant for penetration into and through human nails.	2006-07	16889067
Antifungal agents: mode of action in yeast cells.	2006-06	16964330
Antifungals: need to search for a new molecular target.	2006-04-17	20046765
Treatment options--development of consensus guidelines.	2005-09	16120203
In vitro susceptibility of 15 strains of zygomycetes to nine antifungal agents as determined by the NCCLS M38-A microdilution method.	2005-07	15982206
Pharmacotherapy of onychomycosis.	2005-04	15934887
Candida-related denture stomatitis: a pilot study of the efficacy of an amorolfine antifungal varnish.	2005-03-10	15754893
New insights into the effect of amorolfine nail lacquer.	2005-03	15743424
Treatment of onychomycosis: pros and cons of antifungal agents.	2005-02-03	15688097
Topical antifungal drugs for the treatment of onychomycosis: an overview of current strategies for monotherapy and combination therapy.	2005-01	15649187
Treatment costs of three nail lacquers used in onychomycosis.	2005	16428149
In vitro susceptibility testing of amorolfine in pathogenic fungi isolated from dermatomycosis patients in China.	2004-10	15504124
Allergic contact dermatitis due to amorolfine nail lacquer.	2004-03	15573651
A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers.	2004	15573688
[Assessment of mycological and clinical factors on the course and results of treatment of mycotic infections in patients with recurrent onychomycosis].	2003	15552846
[The treatment of extensive onychomycosis in aged patients].	2001	16886433
Further studies on the in vitro antifungal activity of amorolfine.	1996-01-01	8786756

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 `Wed Apr 02 06:54:16 GMT 2025` Edited by `admin` on `Wed Apr 02 06:54:16 GMT 2025`
Record UNII	AB0BHP2FH0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMOROLFINE

Official Name

English

LOCERYL

Preferred 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

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