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Tolnaftate

Synopsis, Chemistry

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Also known as: 2398-96-1, Tinactin, Tonoftal, Tolnaphthate, Sporiline, Tinaderm

Molecular Formula

C₁₉H₁₇NOS

Molecular Weight

307.4 g/mol

InChI Key

FUSNMLFNXJSCDI-UHFFFAOYSA-N

FDA UNII

06KB629TKV

A synthetic antifungal agent.

1 2D Structure

Tolnaftate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

O-naphthalen-2-yl N-methyl-N-(3-methylphenyl)carbamothioate

2.1.2 InChI

InChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3

2.1.3 InChI Key

FUSNMLFNXJSCDI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=CC=C1)N(C)C(=S)OC2=CC3=CC=CC=C3C=C2

2.2 Other Identifiers

2.2.1 UNII

06KB629TKV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aftate

2. Breezee

3. Chinofungin

4. Chlorisept

5. Curatin

6. Genaspor

7. Micoisdin

8. Np 27

9. Np-27

10. Np27

11. Ony Clear

12. Ony-clear

13. Purder N, Tolnaftat

14. Sporiline

15. Tinactin

16. Tinaderm

17. Tinatox

18. Tineafax

19. Ting

20. Tolnaftat Purder N

21. Tonoftal

22. Zeasorb

2.3.2 Depositor-Supplied Synonyms

1. 2398-96-1

2. Tinactin

3. Tonoftal

4. Tolnaphthate

5. Sporiline

6. Tinaderm

7. Tolsanil

8. Aftate

9. Chinofungin

10. Dermoxin

11. Focusan

12. Tinavet

13. Pitrex

14. Naphthiomate T

15. Phytoderm

16. Timoped

17. Tritin

18. Hi-alazin

19. Fungistop

20. Tolnaftato

21. Tolnaftatum

22. Separin

23. Sorgoa

24. Sch 10144

25. O-2-naphthyl M,n-dimethylthiocarbanilate

26. Dungistop

27. Tniaderm

28. Naphthiomate-t

29. Hi-alarzin

30. 2-naphthyl N-methyl-n-(3-tolyl)thionocarbamate

31. M,n-dimethylthiocarbanilic Acid O-2-naphthyl Ester

32. O-naphthalen-2-yl N-methyl-n-(3-methylphenyl)carbamothioate

33. Prestwick_472

34. Dr. Scholl's Athlete's Foot Spray

35. Methyl (3-methylphenyl)carbamothioic Acid O-2-naphthalenyl Ester

36. Carbamothioic Acid, Methyl(3-methylphenyl)-, O-2-naphthalenyl Ester

37. Carbanilic Acid, M,n-dimethylthio-, O-2-naphthyl Ester

38. Carbanilic Acid, N,m-dimethylthio-, O-2-naphthyl Ester

39. Nsc 233648

40. Mls000028526

41. N-methyl-n-(3-methylphenyl)-1-naphthalen-2-yloxy-methanethioamide

42. O-naphthalen-2-yl N-methyl-n-(3-methylphenyl)thiocarbamate

43. Nsc-233648

44. Smr000058288

45. 06kb629tkv

46. Chebi:9620

47. Tolnaftato [dcit]

48. O-naphthalen-2-yl Methyl(m-tolyl)carbamothioate

49. O-2-naphthyl Methyl(3-methylphenyl)carbamothioate

50. Sch-10144

51. Tolnaftatum [inn-latin]

52. Ncgc00016610-01

53. Tolnaftato [inn-spanish]

54. Tinavet (veterinary)

55. Genaspore Cream

56. Tinactin Powder

57. Cas-2398-96-1

58. Tinactin Cream

59. Pitrex Cream

60. N-methyl-n-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide

61. Ting Products

62. Tinactin Solution

63. Carbamothioic Acid, N-methyl-n-(3-methylphenyl)-, O-2-naphthalenyl Ester

64. Dsstox_cid_22477

65. Dsstox_rid_80034

66. Zeasorb-af Powder

67. Dsstox_gsid_42477

68. Tinactin (tn)

69. Separin (tn)

70. Np-27 Solution

71. Tinactin Plus Powder

72. Ting Antifungal Cream

73. Np-27 Powder

74. Ting Antifungal Powder

75. Np-27 Cream

76. Tinactin Aerosol Liquid

77. Tinactin Aerosol Powder

78. Np-27 Spray Powder

79. Tinactin Jock Itch Cream

80. Aftate For Jock Itch Gel

81. Tinactin Plus Aerosol Powder

82. Ting Antifungal Spray Liquid

83. Ting Antifungal Spray Powder

84. Aftate For Athlete's Foot Gel

85. Tolnafrate

86. Tinactin Jock Itch Spray Powder

87. Tinactin Jock Itch Aerosol Powder

88. Sr-01000003084

89. Aftate For Jock Itch Sprinkle Powder

90. Einecs 219-266-6

91. Brn 2752620

92. Tolnoftate

93. Unii-06kb629tkv

94. Tolnaflate

95. O-2-naphthyl N,n-dimethylthiocarbanilate

96. Aftate For Jock Itch Aerosol Spray Powder

97. Tinactin Antifungal Deodorant Powder Aerosol

98. Methyl-(3-methylphenyl)carbamothioic Acid O-2-naphthyl Ester

99. Tolnaftate-10kg

100. Carbamothiolic Acid

101. O-2-naphthyl Methyl(3-methylphenyl)thiocarbamate

102. Mfcd00056611

103. O-naphthalen-2-yl Methyl(3-methylphenyl)carbamothioate

104. Tolnaftate [usan:usp:inn:ban:jan]

105. Spectrum_000963

106. N-dimethylthiocarbanilate

107. Tolnaftate [mi]

108. Tolnaftate [inn]

109. Tolnaftate [jan]

110. Opera_id_1698

111. Prestwick0_000070

112. Prestwick1_000070

113. Prestwick2_000070

114. Prestwick3_000070

115. Spectrum2_000950

116. Spectrum4_000360

117. Spectrum5_001000

118. Tolnaftate [inci]

119. Tolnaftate [usan]

120. Tolnaftate [vandf]

121. Cid_5510

122. Schembl3520

123. Tolnaftate [mart.]

124. Tolnaftate [usp-rs]

125. Tolnaftate [who-dd]

126. Bspbio_000259

127. Kbiogr_000799

128. Kbioss_001443

129. Mls001146910

130. O-(2-naphthyl) N-methyl-n-(m-tolyl)carbamothioate

131. Chembl83668

132. Divk1c_000334

133. Spectrum1500583

134. Spbio_000920

135. Spbio_002180

136. Bpbio1_000285

137. Tolnaftate (jp17/usp/inn)

138. Tolnaftate [green Book]

139. Dtxsid3042477

140. Bdbm39349

141. Hms501a16

142. Kbio1_000334

143. Kbio2_001443

144. Kbio2_004011

145. Kbio2_006579

146. Tolnaftate For System Suitability

147. Zinc57522

148. Tolnaftate [ep Monograph]

149. Ninds_000334

150. Hms1568m21

151. Hms1921e21

152. Hms2092o05

153. Hms2095m21

154. Hms2231o21

155. Hms3373p10

156. Hms3655d15

157. Hms3712m21

158. Pharmakon1600-01500583

159. Tolnaftate [usp Monograph]

160. Amy23403

161. Bcp12071

162. Hy-b0370

163. Tox21_110521

164. Tox21_301363

165. N-methyl-(3-methylphenyl)-carbamothioic Acid, O-2-naphthalenyl Ester

166. Nsc233648

167. Nsc757355

168. S2058

169. Stl069548

170. Akos005111014

171. Tox21_110521_1

172. Ac-5548

173. Ccg-212827

174. Db00525

175. Ks-5115

176. Nsc-757355

177. Idi1_000334

178. Ncgc00016610-02

179. Ncgc00016610-03

180. Ncgc00016610-04

181. Ncgc00016610-05

182. Ncgc00016610-07

183. Ncgc00016610-08

184. Ncgc00023506-03

185. Ncgc00255761-01

186. Carbamothioic Acid, O-2-naphthalenyl Ester

187. Sbi-0051538.p002

188. Db-046313

189. Ab00052111

190. Ft-0603605

191. Sw196682-3

192. T3059

193. D00381

194. H10435

195. O-naphthalen-2-ylmethyl(m-tolyl)carbamothioate

196. Ab00052111_17

197. Ab00052111_18

198. 398t961

199. A817026

200. O-(naphthalen-2-yl) Methyl(m-tolyl)carbamothioate

201. Q415238

202. Carbanilic Acid,m-dimethylthio-, O-2-naphthyl Ester

203. Carbanilic Acid,n-dimethylthio-, O-2-naphthyl Ester

204. Sr-01000003084-2

205. Sr-01000003084-4

206. W-107363

207. Brd-k44273375-001-04-5

208. Brd-k44273375-001-14-4

209. Brd-k44273375-001-23-5

210. O-(2-naphthyl) Methyl(3-methylphenyl)thiocarbamate #

211. Methyl(3-methylphenyl)carbamothioic Acid O-2-naphthyl Ester

212. N-methyl-n-(m-tolyl)thiocarbamic Acid O-(2-naphthyl) Ester

213. Tolnaftate, European Pharmacopoeia (ep) Reference Standard

214. Tolnaftate, United States Pharmacopeia (usp) Reference Standard

215. Methyl-[3-methyl-2-(2-naphthyl)phenyl]carbamothioic S-acid;tolnaftate

216. N-methyl-n-(3-methylphenyl)carbamothioic Acid O-(2-naphthalenyl) Ester

217. Tolnaftate, Pharmaceutical Secondary Standard; Certified Reference Material

218. Tinactin Pound>>tinaderm Pound>>aftate Pound>>np-27 Pound>>np 27 Pound>> Np27

219. Tolnaftate For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₇NOS
Molecular Weight	307.4 g/mol
XLogP3	5.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	307.10308534 g/mol
Monoisotopic Mass	307.10308534 g/mol
Topological Polar Surface Area	44.6 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	386
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Tolnaftate topical is used to treat skin infections such as athlete's foot, jock itch, and ringworm infections. Tolnaftate is also used, along with other antifungals, to treat infections of the nails, scalp, palms, and soles of the feet. The powder and powder aerosol may be used to prevent athlete's foot.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tolnaftate is a synthetic over-the-counter anti-fungal agent.

5.2 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Azoles [CS]; Azole Antifungal [EPC]

5.4 ATC Code

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AE - Other antifungals for topical use

D01AE18 - Tolnaftate

5.5 Mechanism of Action

Tolnaftate is a topical fungicide. Though its exact mechanism unknown, it is believed to prevent ergosterol biosynthesis by inhibiting squalene epoxidase. It has also been reported to distort the hyphae and to stunt mycelial growth in susceptible organisms.

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