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    Tolnaftate

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    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

    2D Structure

    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 Weight 307.4 g/mol
    Molecular Formula C19H17NOS
    XLogP35.5
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count3
    Exact Mass307.10308534 g/mol
    Monoisotopic Mass307.10308534 g/mol
    Topological Polar Surface Area44.6 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity386
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.