Naftifine HCl | AW-105843 | CAS#65473-14-5 | 65472-88-0 | antifungal

MedKoo Cat#: 318299 | Name: Naftifine HCl

Description:

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

Naftifine is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis (fungal infections). Its precise mechanism of action is unknown, but may involve selectively blocking sterol biosynthesis via inhibition of the squalene 2,3-epoxidase enzyme. The half-life is approximately 2–3 days. The metabolites are excreted in the urine and feces.

Chemical Structure

Naftifine HCl

CAS#65473-14-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 318299

Name: Naftifine HCl

CAS#: 65473-14-5 (HCl)

Chemical Formula: C21H22ClN

Exact Mass: 0.0000

Molecular Weight: 323.86

Elemental Analysis: C, 77.88; H, 6.85; Cl, 10.95; N, 4.32

Price and Availability

Size	Price	Availability	Quantity
1g	USD 750.00	2 Weeks
5g	USD 1,950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

65473-14-5 (HCl) 65472-88-0 (free base)

Synonym

AW 105843; AW105843; AW-105843; AW 105-843; SN 105843; SN105843; SN-105843; Naftifine, Naftifine hydrochloride; Naftin

IUPAC/Chemical Name

(E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine hydrochloride

InChi Key

PGYDRGZVXVVZQC-LLVKDONJSA-N

InChi Code

InChI=1S/C15H19N5/c1-11(15(2,3)4)19-14(18-10-17)20-13-7-5-12(9-16)6-8-13/h5-8,11H,1-4H3,(H2,18,19,20)/t11-/m1/s1

SMILES Code

CN(CC1=C2C=CC=CC2=CC=C1)C/C=C/C3=CC=CC=C3.[H]Cl

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, not in water

Shelf Life

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Naftifine hydrochloride is an antibiotic.

In vitro activity:

Naftifine exhibits an interesting in vitro spectrum of activity against dermatophytes (38 strains; minimal inhibitory concentration [MIC] range 0.1 to 0.2 microgram/ml), aspergilli (6 strains; MIC range, 0.8 to 12.5 microgram/ml), Sporothrix schenckii (2 strains; MICs, 0.8 and 1.5 microgram/ml), and yeasts of the genus Candida (77 strains; MIC range, 1.5 to greater than 100 microgram/ml). Its degree of efficacy is unaffected by the organism density in the test medium, and it is primarily fungicidal against dermatophytes as well as yeasts. Its in vitro efficacy is pH dependent and rises with increasing pH values. Reference: Antimicrob Agents Chemother. 1981 Mar;19(3):386-9. https://pubmed.ncbi.nlm.nih.gov/7247366/

In vivo activity:

Naftifine, a new antifungal agent belonging chemically to the allylamines, was tested for its in vivo activity after topical application against guinea pig skin infections caused by Trichophyton mentagrophytes, T. mentagrophytes var. quinckeanum, or Microsporum racemosum. Compared with standard compounds, naftifine proved to be highly effective mycologically and clinically after topical application in the above models. Reference: Antimicrob Agents Chemother. 1981 Mar;19(3):390-2. https://pubmed.ncbi.nlm.nih.gov/7247367/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	30.88
	DMF:PBS (pH 7.2) (1:5)	0.2	0.49
	DMSO	52.5	162.11
	Ethanol	12.7	39.11

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 323.86 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

Formulation protocol:

1. Ryder NS, Seidl G, Troke PF. Effect of the antimycotic drug naftifine on growth of and sterol biosynthesis in Candida albicans. Antimicrob Agents Chemother. 1984 Apr;25(4):483-7. doi: 10.1128/AAC.25.4.483. PMID: 6375557; PMCID: PMC185557. 2. Georgopoulos A, Petranyi G, Mieth H, Drews J. In vitro activity of naftifine, a new antifungal agent. Antimicrob Agents Chemother. 1981 Mar;19(3):386-9. doi: 10.1128/AAC.19.3.386. PMID: 7247366; PMCID: PMC181441. 3. Petranyi G, Georgopoulos A, Mieth H. In vivo antimycotic activity of naftifine. Antimicrob Agents Chemother. 1981 Mar;19(3):390-2. doi: 10.1128/AAC.19.3.390. PMID: 7247367; PMCID: PMC181442.

In vitro protocol:

In vivo protocol:

1. Petranyi G, Georgopoulos A, Mieth H. In vivo antimycotic activity of naftifine. Antimicrob Agents Chemother. 1981 Mar;19(3):390-2. doi: 10.1128/AAC.19.3.390. PMID: 7247367; PMCID: PMC181442.

1: Del Rosso JQ, Kircik LH. Optimizing topical antifungal therapy for superficial cutaneous fungal infections: focus on topical naftifine for cutaneous dermatophytosis. J Drugs Dermatol. 2013 Nov;12(11 Suppl):s165-71. Review. PubMed PMID: 24196340. 2: Gupta AK, Ryder JE, Cooper EA. Naftifine: a review. J Cutan Med Surg. 2008 Mar-Apr;12(2):51-8. Review. PubMed PMID: 18346400. 3: Mühlbacher JM. Naftifine: a topical allylamine antifungal agent. Clin Dermatol. 1991 Oct-Dec;9(4):479-85. Review. PubMed PMID: 1822408. 4: Monk JP, Brogden RN. Naftifine. A review of its antimicrobial activity and therapeutic use in superficial dermatomycoses. Drugs. 1991 Oct;42(4):659-72. Review. PubMed PMID: 1723367.