Amorolfine | CAS#67467-83-8 | antifungal

MedKoo Cat#: 461377 | Name: Amorolfine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Amorolfine is commonly available in the form of a nail lacquer. It is a topical application used to treat fungal nail infections.

Chemical Structure

Amorolfine

CAS#78613-35-1 (free base)

Theoretical Analysis

MedKoo Cat#: 461377

Name: Amorolfine

CAS#: 78613-35-1 (free base)

Chemical Formula: C21H35NO

Exact Mass: 317.2719

Molecular Weight: 317.51

Elemental Analysis: C, 79.44; H, 11.11; N, 4.41; O, 5.04

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Related CAS #

67467-83-8 78613-35-1 (free base) 78613-38-4 (HCl)

Synonym

Amorolfine; Ro 14-4767-002; Ro-14-4767-002; Ro14-4767-002; Ro 14-4767; Ro-14-4767; Ro14-4767; Ro 144767; Ro-144767; Ro144767;

IUPAC/Chemical Name

2,6-dimethyl-4-(2-methyl-3-(4-(tert-pentyl)phenyl)propyl)morpholine

InChi Key

MQHLMHIZUIDKOO-UHFFFAOYSA-N

InChi Code

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

SMILES Code

CC1OC(C)CN(CC(C)CC2=CC=C(C(C)(C)CC)C=C2)C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 317.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Tabara K, Szewczyk AE, Bienias W, Wojciechowska A, Pastuszka M, Oszukowska M, Kaszuba A. Amorolfine vs. ciclopirox - lacquers for the treatment of onychomycosis. Postepy Dermatol Alergol. 2015 Feb;32(1):40-5. doi: 10.5114/pdia.2014.40968. Epub 2015 Feb 3. Review. PubMed PMID: 25821426; PubMed Central PMCID: PMC4360009. 2: Auvinen T, Tiihonen R, Soini M, Wangel M, Sipponen A, Jokinen JJ. Efficacy of topical resin lacquer, amorolfine and oral terbinafine for treating toenail onychomycosis: a prospective, randomized, controlled, investigator-blinded, parallel-group clinical trial. Br J Dermatol. 2015 Oct;173(4):940-8. doi: 10.1111/bjd.13934. Epub 2015 Oct 1. PubMed PMID: 26036329. 3: Bunyaratavej S, Leeyaphan C, Rujitharanawong C, Surawan TM, Muanprasat C, Matthapan L. Efficacy of 5% amorolfine nail lacquer in Neoscytalidium dimidiatum onychomycosis. J Dermatolog Treat. 2016 Aug;27(4):359-63. doi: 10.3109/09546634.2015.1109029. Epub 2015 Nov 11. PubMed PMID: 26471716. 4: Sigurgeirsson B, Ghannoum MA, Osman-Ponchet H, Kerrouche N, Sidou F. Application of cosmetic nail varnish does not affect the antifungal efficacy of amorolfine 5% nail lacquer in the treatment of distal subungual toenail onychomycosis: results of a randomised active-controlled study and in vitro assays. Mycoses. 2016 May;59(5):319-26. doi: 10.1111/myc.12473. Epub 2016 Feb 11. PubMed PMID: 26867498. 5: Seidl HP, Jäckel A, Müller J, Schaller M, Borelli C, Polak A. Sporicidal effect of amorolfine and other antimycotics used in the therapy of fungal nail infections. Mycoses. 2015 Oct;58(10):610-9. doi: 10.1111/myc.12369. Epub 2015 Sep 3. PubMed PMID: 26334024. 6: Iorizzo M, Hartmane I, Derveniece A, Mikazans I. Ciclopirox 8% HPCH Nail Lacquer in the Treatment of Mild-to-Moderate Onychomycosis: A Randomized, Double-Blind Amorolfine Controlled Study Using a Blinded Evaluator. Skin Appendage Disord. 2016 Feb;1(3):134-40. doi: 10.1159/000441569. Epub 2015 Nov 7. Erratum in: Skin Appendage Disord. 2016 May;1(4):168. PubMed PMID: 27171791; PubMed Central PMCID: PMC4857848. 7: Monti D, Tampucci S, Chetoni P, Burgalassi S, Mailland F. Ciclopirox vs amorolfine: in vitro penetration into and permeation through human healthy nails of commercial nail lacquers. J Drugs Dermatol. 2014 Feb;13(2):143-7. PubMed PMID: 24509963. 8: Chen S, Ran YP, Dai YL, Lama J, Hu WY. Case of infantile onychomycosis successfully cured by 5% amorolfine nail lacquer. J Paediatr Child Health. 2014 Nov;50(11):933-4. doi: 10.1111/jpc.12740. PubMed PMID: 25376356. 9: Zhang J, Lu S, Huang H, Li X, Cai W, Ma J, Xi L. Combination therapy for onychomycosis using a fractional 2940-nm Er:YAG laser and 5 % amorolfine lacquer. Lasers Med Sci. 2016 Sep;31(7):1391-6. doi: 10.1007/s10103-016-1990-z. Epub 2016 Jun 23. PubMed PMID: 27339057. 10: Yong AS. Resin lacquer: a cheaper alternative to amorolfine for onychomycosis? Br J Dermatol. 2015 Oct;173(4):888-9. doi: 10.1111/bjd.13982. PubMed PMID: 26511823. 11: Ghannoum M, Sevin K, Sarkany M. Amorolfine 5% Nail Lacquer Exhibits Potent Antifungal Activity Compared to Three Acid-Based Devices Indicated for the Treatment of Onychomycosis: An In Vitro Nail Penetration Assay. Dermatol Ther (Heidelb). 2016 Mar;6(1):69-75. doi: 10.1007/s13555-016-0093-x. Epub 2016 Feb 1. Erratum in: Dermatol Ther (Heidelb). 2016 Sep;6(3):451. PubMed PMID: 26833478; PubMed Central PMCID: PMC4799031. 12: Tamura T, Asahara M, Yamamoto M, Yamaura M, Matsumura M, Goto K, Rezaei-Matehkolaei A, Mirhendi H, Makimura M, Makimura K. In vitro susceptibility of dermatomycoses agents to six antifungal drugs and evaluation by fractional inhibitory concentration index of combined effects of amorolfine and itraconazole in dermatophytes. Microbiol Immunol. 2014 Jan;58(1):1-8. doi: 10.1111/1348-0421.12109. PubMed PMID: 24215461. 13: Paul C, Coustou D, Lahfa M, Bulai-Livideanu C, Doss N, Mokthar I, Turki H, Nouira R, Fazaa B, Ben Osman A, Zourabichvili O, Cazeau C, Coubetergues H, Picot S, Bienvenu AL, Voisard JJ. A multicenter, randomized, open-label, controlled study comparing the efficacy, safety and cost-effectiveness of a sequential therapy with RV4104A ointment, ciclopiroxolamine cream and ciclopirox film-forming solution with amorolfine nail lacquer alone in dermatophytic onychomycosis. Dermatology. 2013;227(2):157-64. PubMed PMID: 24051622. 14: Gao Y, Li L, Zhang J, Shu W, Gao L. Simultaneous determination of triacetin, acetic ether, butyl acetate and amorolfine hydrochloride in amorolfine liniment by HPLC. Pak J Pharm Sci. 2012 Apr;25(2):389-94. PubMed PMID: 22459467. 15: Morales-Molina JA, Fayet-Pérez A, Martínez-Plata E, Pérez-Moyano R, Molina-Arrebola MA. Interaction between amorolfine and acenocoumarol. Eur J Clin Pharmacol. 2012 Dec;68(12):1687-8. doi: 10.1007/s00228-012-1305-7. Epub 2012 May 31. PubMed PMID: 22648278. 16: Morais OO, Costa IM, Gomes CM, Shinzato DH, Ayres GM, Cardoso RM. The use of the Er:YAG 2940nm laser associated with amorolfine lacquer in the treatment of onychomycosis. An Bras Dermatol. 2013 Sep-Oct;88(5):847-9. doi: 10.1590/abd1806-4841.20131932. PubMed PMID: 24173203; PubMed Central PMCID: PMC3798374. 17: Monti D, Herranz U, Dal Bo L, Subissi A. Nail penetration and predicted mycological efficacy of an innovative hydrosoluble ciclopirox nail lacquer vs. a standard amorolfine lacquer in healthy subjects. J Eur Acad Dermatol Venereol. 2013 Feb;27(2):e153-8. doi: 10.1111/j.1468-3083.2012.04529.x. Epub 2012 Mar 26. PubMed PMID: 22449201. 18: Nolting S, Semig G, Friedrich HK, Dietz M, Reckers-Czaschka R, Bergstraesser M, Zaug M. Double-blind comparison of amorolfine and bifonazole in the treatment of dermatomycoses. Clin Exp Dermatol. 1992 Sep;17 Suppl 1:56-60. PubMed PMID: 1458667. 19: Stensen W, Turner R, Brown M, Kondori N, Svendsen JS, Svenson J. Short Cationic Antimicrobial Peptides Display Superior Antifungal Activities toward Candidiasis and Onychomycosis in Comparison with Terbinafine and Amorolfine. Mol Pharm. 2016 Oct 3;13(10):3595-3600. Epub 2016 Sep 6. PubMed PMID: 27576445. 20: Polak A. Preclinical data and mode of action of amorolfine. Dermatology. 1992;184 Suppl 1:3-7. PubMed PMID: 1550968.