AMOROLFINE HYDROCHLORIDE

Details

Stereochemistry	MIXED
Molecular Formula	C21H35NO.ClH
Molecular Weight	353.97
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XZKWIPVTHGWDCF-KUZYQSSXSA-N

InChI=1S/C21H35NO.ClH/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;1H/t16?,17-,18+;

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H35NO
Molecular Weight	317.5087
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 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
Further studies on the in vitro antifungal activity of amorolfine.	1996 Jan-Feb	8786756
[The treatment of extensive onychomycosis in aged patients].	2001	16886433
[Assessment of mycological and clinical factors on the course and results of treatment of mycotic infections in patients with recurrent onychomycosis].	2003	15552846
A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers.	2004	15573688
Treatment of onychomycosis: pros and cons of antifungal agents.	2004 Jan-Feb	15688097
Allergic contact dermatitis due to amorolfine nail lacquer.	2004 Mar	15573651
In vitro susceptibility testing of amorolfine in pathogenic fungi isolated from dermatomycosis patients in China.	2004 Oct	15504124
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
New insights into the effect of amorolfine nail lacquer.	2005 Mar	15743424
Treatment options--development of consensus guidelines.	2005 Sep	16120203
Sublimation of antimycotic agents as proved by various analytical methods.	2006 Dec	17283666
Different physicochemical properties of antimycotic agents are relevant for penetration into and through human nails.	2006 Jul	16889067
Rapid response of distal subungual onychomycosis to 5% amorolfine nail lacquer in a 20-month-old healthy infant.	2006 Jul-Aug	16918646
Antifungal agents: mode of action in yeast cells.	2006 Jun	16964330
Onychomycosis in the elderly : drug treatment options.	2007	17432924
Toenail onychomycosis: current and future treatment options.	2007 Jan-Feb	17403258
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 Jul	17553051
Topical treatments for fungal infections of the skin and nails of the foot.	2007 Jul 18	17636672
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 Nov-Dec	18032857
1-Phenylethynylpyrene (1-PEPy) as refined excimer forming alternative to pyrene: case of DNA major groove excimer.	2007 Nov-Dec	17896811
Review of antifungal therapy and the severity index for assessing onychomycosis: part I.	2008	18484426
In vitro antifungal activity of sertaconazole nitrate against recent isolates of onychomycosis causative agents.	2008 Aug	18676237
Pooling overdispersed binomial data to estimate event rate.	2008 Aug 19	18713448
Tinea capitis due to Trichophyton soudanense with a papular IDE reaction in Northern Italy.	2008 Dec	19169215
Fungal toenail infections.	2008 Dec 15	19445781
Antifungals: need to search for a new molecular target.	2008 Jul-Aug	20046765
Treatment of onychomycosis: an update.	2008 Nov	21369429
Update in antifungal therapy of dermatophytosis.	2008 Nov-Dec	18478357
[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
Rapid detection of dermatophytes from skin and hair.	2009 Apr 18	19374765
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
Susceptibility testing of amorolfine, bifonazole and ciclopiroxolamine against Trichophyton rubrum in an in vitro model of dermatophyte nail infection.	2009 Nov	19888808
Onychomycosis and diabetes.	2009 Oct	19309423
Onychomycosis insensitive to systemic terbinafine and azole treatments reveals non-dermatophyte moulds as infectious agents.	2010	20110639
[Allergic contact dermatitis due to amorolfine in nail lacquer].	2010 Apr	20398612
Efficacy of amorolfine nail lacquer for the prophylaxis of onychomycosis over 3 years.	2010 Aug	20028447
Hydrosoluble medicated nail lacquers: in vitro drug permeation and corresponding antimycotic activity.	2010 Feb 1	19886884
Effect of a novel penetration enhancer on the ungual permeation of two antifungal agents.	2010 Jun	20636860
Chemical combinations elucidate pathway interactions and regulation relevant to Hepatitis C replication.	2010 Jun 8	20531405
Long-term follow-up of toenail onychomycosis caused by dermatophytes after successful treatment with systemic antifungal agents.	2010 Mar	20159308
Onychomycosis.	2010 Mar 4	20347657

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 `Fri Dec 15 16:22:25 GMT 2023` Edited by `admin` on `Fri Dec 15 16:22:25 GMT 2023`
Record UNII	741YH7379H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMOROLFINE HYDROCHLORIDE

Common Name

English

AMOROLFINE HYDROCHLORIDE [MI]

Common Name

English

AMOROLFINE HCL

Common Name

English

AMOROLFINE HYDROCHLORIDE [MART.]

Common Name

English

AMOROLFINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

Amorolfine hydrochloride [WHO-DD]

Common Name

English

AMOROLFINE HYDROCHLORIDE [JAN]

Common Name

English

AMOROLFINE (AS HYDROCHLORIDE)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514