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

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
Potent synergism of the combination of fluconazole and cyclosporine in Candida albicans.	2000 Sep	10952582
The rationale for combination therapy.	2001 Oct	11777263
A randomized trial of amorolfine 5% solution nail lacquer in association with itraconazole pulse therapy compared with itraconazole alone in the treatment of Candida fingernail onychomycosis.	2003 Jul	12890209
Pharmacoeconomic issues in onychomycosis.	2003 Sep	14510972
Combination therapy for onychomycosis.	2003 Sep	14510971
Actin gene-targeted RT-PCR could be a useful method for evaluating in vitro fungicidal activity against dermatophytes.	2003 Sep-Oct	14587308
Common fungal infections of the feet in patients with diabetes mellitus.	2004	14960127
Pharmacotherapy of onychomycosis.	2005 Apr	15934887
Onychomycosis in the elderly : drug treatment options.	2007	17432924
Toenail onychomycosis: current and future treatment options.	2007 Jan-Feb	17403258
Tinea capitis due to Trichophyton soudanense with a papular IDE reaction in Northern Italy.	2008 Dec	19169215
Antifungals: need to search for a new molecular target.	2008 Jul-Aug	20046765
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
Onychomycosis insensitive to systemic terbinafine and azole treatments reveals non-dermatophyte moulds as infectious agents.	2010	20110639
Long-term follow-up of toenail onychomycosis caused by dermatophytes after successful treatment with systemic antifungal agents.	2010 Mar	20159308

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.

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