Antifungal nail coat and method of use

Abstract

Antifungal nail coat compositions containing an allylamine, an N,N-di(C 1 -C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester or a pharmaceutically acceptable acid addition salt thereof, a hydrophilic polymer, and a pharmaceutically acceptable, volatile organic carrier are disclosed. The composition provides a substantially water-soluble, fungicidal coating upon contact with a fungally susceptible or infected nail.

1 . An antifungal nail coat composition comprising:
 a fungicidal amount of an allylamine;   an N,N-di(C 1 -C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester or pharmaceutically acceptable acid addition salt thereof;   a film-forming amount of a hydrophilic polymer; and   a pharmaceutically acceptable, volatile organic carrier,   the composition providing a substantially water-soluble, fungicidal coating on contacting a fungally susceptible or infected nail.   
   
   
       2 . The antifungal nail coat composition of  claim 1  wherein the allylamine is terbinafine. 
   
   
       3 . The antifungal nail coat composition of  claim 1  wherein N,N-di(C 1 -C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester addition salt is dodecyl-2-(N,N-dimethylamino) isopropionate hydrochloride. 
   
   
       4 . The antifungal nail coat composition of  claim 1  further including an aromatic alcohol. 
   
   
       5 . The antifungal nail coat composition of  claim 4  wherein the aromatic alcohol is benzyl alcohol. 
   
   
       6 . The antifungal nail coat composition of  claim 1  wherein the hydrophilic polymer is selected from the group consisting of a polymer comprising a vinylpyrrolidone monomer unit, a gum, and a resin. 
   
   
       7 . The antifungal nail coat composition of  claim 1  wherein the hydrophilic polymer comprises a vinylpyrrolidone monomer unit selected from a homopolymer thereof, a copolymer thereof, and a complex thereof. 
   
   
       8 . The antifungal nail coat composition of  claim 1  wherein the hydrophilic polymer is a polyvinylpyrrolidone. 
   
   
       9 . The antifungal nail coat composition of  claim 1  wherein the carrier is an alkanol having 2 to about 5 carbon atoms. 
   
   
       10 . The antifungal nail coat composition of  claim 1  wherein the carrier is ethanol. 
   
   
       11 . The antifungal nail coat composition of  claim 1  wherein the allylamine is present, on a total composition weight basis, in an amount in the range of about 0.1 to about 20 weight percent. 
   
   
       12 . The antifungal nail coat composition of  claim 1  wherein the allylamine is present, on a total composition weight basis, in an amount in the range of about 0.5 to about 15 weight percent. 
   
   
       13 . The antifungal nail coat composition of  claim 1  wherein the allylamine is terbinafine hydrochloride. 
   
   
       14 . The antifungal nail coat composition of  claim 13  wherein the terbinafine hydrochloride is present, on a total composition weight basis, in an amount in the range of about 0.5 to about 10 weight percent. 
   
   
       15 . The antifungal nail coat composition of  claim 13  wherein the terbinafine hydrochloride is present, on a total composition weight basis, in an amount in the range of about 1 to about 5 weight percent. 
   
   
       16 . The antifungal nail coat composition of  claim 13  wherein, on a total composition weight basis, the N,N-di(C 1 -C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester acid addition salt is present in an amount in the range of about 0.1 to about 25 weight percent. 
   
   
       17 . The antifungal nail coat composition of  claim 13  wherein the N,N-di(C 1 -C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester acid addition salt is dodecyl-2-(N,N-dimethylamino) isopropionate hydrochloride and is present in an amount in the range of about 0.1 to about 10 weight percent, on a total composition weight basis. 
   
   
       18 . The antifungal nail coat composition of  claim 17  further including about 0.1 to about 10 weight percent benzyl alcohol. 
   
   
       19 . The antifungal nail coat composition of  claim 1  wherein, on a total composition weight basis, the hydrophilic polymer is present in an amount in the range of about 0.25 to about 1 weight percent. 
   
   
       20 . An antifungal nail coat composition comprising, on a total composition weight basis:
 about 0.5 to about 10 weight percent terbinafine hydrochloride;   about 0.1 to about 25 weight percent dodecyl-2-(N,N-dimethylamino) isopropionate hydrochloride;   about 0.1 to about 10 weight percent benzyl alcohol;   about 0.1 to about 5 percent polyvinylpyrrolidone; and   ethanol comprising the remainder.   
   
   
       21 . A method of ameliorating or preventing fungal infection of a toenail or fingernail comprising contacting a fungally susceptible or infected nail and skin tissue adjacent thereto with a nail coat composition of  claim 1  to provide a substantially uniform fungicidal coating thereon, and maintaining said contact for a period of at least about 0.5 hour. 
   
   
       22 . The method of  claim 21  wherein the method is performed at least once a day.