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    Chemistry

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    Also known as: Terbinafine hcl, 78628-80-5, Lamisil at, (e)-n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride, Bramazil, Bramizil
    Molecular Formula
    C21H26ClN
    Molecular Weight
    327.9  g/mol
    InChI Key
    BWMISRWJRUSYEX-SZKNIZGXSA-N
    FDA UNII
    012C11ZU6G
    Terbinafine Hydrochloride
    A naphthalene derivative that inhibits fungal SQUALENE EPOXIDASE and is used to treat DERMATOMYCOSES of the skin and nails.
    1 2D Structure

    Terbinafine Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine;hydrochloride
    2.1.2 InChI
    InChI=1S/C21H25N.ClH/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19;/h5-7,9-14H,16-17H2,1-4H3;1H/b9-5+;
    2.1.3 InChI Key
    BWMISRWJRUSYEX-SZKNIZGXSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=CC=CC=C21.Cl
    2.1.5 Isomeric SMILES
    CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    012C11ZU6G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (e)-n-(6,6-dimethyl-2-heptenynyl)-n-methyl-1-naphthalenementhamin Hydrochloride

    2. Da 5505

    3. Lamisil

    4. Sf 86 327

    5. Sf 86-327

    6. Sf 86327

    7. Sf-86-327

    8. Sf86327

    9. Tdt 067

    10. Tdt-067

    11. Tdt067

    12. Terbinafine

    13. Terbinafine, (z)-

    14. Terbinafine, (z)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. Terbinafine Hcl

    2. 78628-80-5

    3. Lamisil At

    4. (e)-n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine Hydrochloride

    5. Bramazil

    6. Bramizil

    7. Muzonal

    8. Terbina

    9. Terbine

    10. Terbinafina

    11. Terbinafinum

    12. Zabel

    13. Nsc-759113

    14. Cpd000469152

    15. Terbinafine (as Hydrochloride)

    16. Chebi:77614

    17. 012c11zu6g

    18. (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalenemethylamine Hydrochloride

    19. Trans-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthylmethylamine Hydrochloride

    20. 78628-80-5 (hcl)

    21. Lamisil Krem

    22. Trans-n-(6,6-dimethyl-2-hepten-4-ylyl)-n-methyl-1-naphthylmethylamine Hydrochloride

    23. Terbinafinum [latin]

    24. Terbinafina [spanish]

    25. Athletes Foot

    26. Mycova

    27. (e)-n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine;hydrochloride

    28. [(2e)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine Hydrochloride

    29. N-[(2e)-6,6-dimethyl-2-hepten-4-yn-1-yl]-n-methyl-1-naphthalenemethanamine Hydrochloride

    30. Sf 86-327 Hydrochloride

    31. Smr000469152

    32. N,6,6-trimethyl-n-(1-naphthylmethyl)hept-2-en-4-yn-1-amine Hydrochloride

    33. Drg-0286

    34. Terbinafine (hydrochloride)

    35. Terbisil

    36. Afogan

    37. Terbifoam

    38. Innonyx

    39. Unii-012c11zu6g

    40. Lamisil (tn)

    41. Terbinafine Hydrochloride [usp:jan]

    42. Mfcd00145430

    43. Terbinafine,hydrochloride

    44. Ec 616-640-4

    45. Terbinafine Monohydrochloride

    46. Schembl36793

    47. Schembl36795

    48. Mls001066620

    49. Mls001304037

    50. Mls001401424

    51. Terbinafine Hydrochloride,(s)

    52. Chembl1200832

    53. Dtxsid90229223

    54. Htu-520

    55. Pharmakon1600-01505392

    56. Terbinafine Hydrochloride, >=98%

    57. Terbinafine Hydrochloride (lamisil)

    58. Ac-761

    59. Nsc759113

    60. S2557

    61. Terbinafine Hydrochloride [mi]

    62. Akos015844100

    63. Akos025149216

    64. Terbinafine Hydrochloride (jp17/usp)

    65. Bcp9000834

    66. Ccg-101026

    67. Cs-1123

    68. Ks-1289

    69. Nc00276

    70. Nsc 759113

    71. Terbinafine Hydrochloride [jan]

    72. Terbinafine Hydrochloride [mart.]

    73. Terbinafine Hydrochloride [vandf]

    74. 1-naphthalenemethanamine, N-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-, (e)-, Monohydrochloride

    75. 1-naphthalenemethanamine, N-[(2e)-6,6-dimethyl-2-hepten-4-yn-1-yl]-n-methyl-, Hydrochloride (1:1)

    76. Bt164461

    77. Hy-17395

    78. Ls-14899

    79. Sf-86327

    80. Terbinafine Hydrochloride [usp-rs]

    81. Terbinafine Hydrochloride [who-dd]

    82. Nm-100060

    83. B2047

    84. D2049

    85. Sw197656-2

    86. D02219

    87. Terbinafine Hydrochloride [ep Monograph]

    88. Terbinafine Hydrochloride [orange Book]

    89. Terbinafine Hydrochloride [usp Monograph]

    90. 628t805

    91. A839463

    92. Q-201790

    93. Q27147212

    94. Terbinafine Hydrochloride, Antibiotic For Culture Media Use Only

    95. Terbinafine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    96. (2e)-n,6,6-trimethyl-n-(1-naphthylmethyl)hept-2-en-4-yn-1-amine Hydrochloride

    97. (2e)-n,6,6-trimethyl-n-(1-naphthylmethyl)hept-2-en-4-yn-1-amine Hydrochloride (1:1)

    98. (2e)-n,6,6-trimethyl-n-(1-naphthylmethyl)hept-2-en-4-yn-1-aminium Chloride

    99. (2e)-n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine Hydrochloride

    100. (e)-n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-aminehydrochloride

    101. (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalenemethanamine Hydrochloride

    102. (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthylmethylamine Hydrochloride

    103. [(e)-6,6-dimethylhept-2-en-4-ynyl]-methyl-(naphthalen-1-ylmethyl)azanium;chloride

    104. Terbinafine For System Suitability, European Pharmacopoeia (ep) Reference Standard

    105. Terbinafine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

    106. Terbinafine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    107. (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalenemethylamine, Hydrochloride

    108. 1-naphthalenemethanamine, N-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-, (e)-, Hydrochloride

    2.4 Create Date
    2005-10-11
    3 Chemical and Physical Properties
    Molecular Weight 327.9 g/mol
    Molecular Formula C21H26ClN
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count5
    Exact Mass327.1753775 g/mol
    Monoisotopic Mass327.1753775 g/mol
    Topological Polar Surface Area3.2 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity428
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameLamisil
    Drug LabelLamisil Tablets contain the synthetic allylamine antifungal compound terbinafine hydrochloride.Chemically, terbinafine hydrochloride is (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine hydrochloride. The empirical formula C21H26...
    Active IngredientTerbinafine hydrochloride
    Dosage FormTablet; Cream; Granule
    RouteOral; Topical
    Strengtheq 187.5mg base/packet; 1%; eq 250mg base; eq 125mg base/packet
    Market StatusOver the Counter; Prescription
    CompanyNovartis

    2 of 6  
    Drug NameLamisil at
    Active IngredientTerbinafine hydrochloride; Terbinafine
    Dosage FormSpray; Gel; Solution
    RouteTopical
    Strength1%
    Market StatusOver the Counter
    CompanyNovartis

    3 of 6  
    Drug NameTerbinafine hydrochloride
    PubMed HealthTerbinafine
    Drug ClassesAntifungal
    Drug LabelTerbinafine hydrochloride tablets contain the synthetic allylamine antifungal compound terbinafine hydrochloride.Chemically, terbinafine hydrochloride is (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine hydrochloride. The empiri...
    Active IngredientTerbinafine hydrochloride
    Dosage FormTablet; Cream
    Routeoral; Oral; Topical
    Strength1%; eq 250mg base
    Market StatusTentative Approval; Over the Counter; Prescription
    CompanyWockhardt; Harris Pharm; Breckenridge Pharm; Teva; Apotex; Aurobindo Pharma; Taro; Andrx Pharm; Invagen Pharms; Cipla; Glenmark Generics; Dr Reddys Labs; Orchid Hlthcare; Mylan

    4 of 6  
    Drug NameLamisil
    Drug LabelLamisil Tablets contain the synthetic allylamine antifungal compound terbinafine hydrochloride.Chemically, terbinafine hydrochloride is (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine hydrochloride. The empirical formula C21H26...
    Active IngredientTerbinafine hydrochloride
    Dosage FormTablet; Cream; Granule
    RouteOral; Topical
    Strengtheq 187.5mg base/packet; 1%; eq 250mg base; eq 125mg base/packet
    Market StatusOver the Counter; Prescription
    CompanyNovartis

    5 of 6  
    Drug NameLamisil at
    Active IngredientTerbinafine hydrochloride; Terbinafine
    Dosage FormSpray; Gel; Solution
    RouteTopical
    Strength1%
    Market StatusOver the Counter
    CompanyNovartis

    6 of 6  
    Drug NameTerbinafine hydrochloride
    PubMed HealthTerbinafine
    Drug ClassesAntifungal
    Drug LabelTerbinafine hydrochloride tablets contain the synthetic allylamine antifungal compound terbinafine hydrochloride.Chemically, terbinafine hydrochloride is (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine hydrochloride. The empiri...
    Active IngredientTerbinafine hydrochloride
    Dosage FormTablet; Cream
    Routeoral; Oral; Topical
    Strength1%; eq 250mg base
    Market StatusTentative Approval; Over the Counter; Prescription
    CompanyWockhardt; Harris Pharm; Breckenridge Pharm; Teva; Apotex; Aurobindo Pharma; Taro; Andrx Pharm; Invagen Pharms; Cipla; Glenmark Generics; Dr Reddys Labs; Orchid Hlthcare; Mylan

    4.2 Drug Indication

    Treatment of onychomycosis

    5 Pharmacology and Biochemistry
    5.1 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.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Allylamine [CS]; Allylamine Antifungal [EPC]

    API Reference Price

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    18-Jan-2021
    21-Nov-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - TABLET;ORAL - EQ 250MG BASE **Federa...DOSAGE - TABLET;ORAL - EQ 250MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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    USFDA APPLICATION NUMBER - 20980

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