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    Chemistry

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    Also known as: 91161-71-6, Lamisil, Lamasil, (e)-n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine, Sf-86-327, Lamisil at
    Molecular Formula
    C21H25N
    Molecular Weight
    291.4  g/mol
    InChI Key
    DOMXUEMWDBAQBQ-WEVVVXLNSA-N
    FDA UNII
    G7RIW8S0XP
    Terbinafine
    A naphthalene derivative that inhibits fungal SQUALENE EPOXIDASE and is used to treat DERMATOMYCOSES of the skin and nails.
    Terbinafine is an Allylamine Antifungal.
    1 2D Structure

    Terbinafine

    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
    2.1.2 InChI
    InChI=1S/C21H25N/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/b9-5+
    2.1.3 InChI Key
    DOMXUEMWDBAQBQ-WEVVVXLNSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=CC=CC=C21
    2.1.5 Isomeric SMILES
    CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21
    2.2 Other Identifiers
    2.2.1 UNII
    G7RIW8S0XP
    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 Hydrochloride

    13. Terbinafine, (z)-

    14. Terbinafine, (z)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 91161-71-6

    2. Lamisil

    3. Lamasil

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

    5. Sf-86-327

    6. Lamisil At

    7. Sf 86-327

    8. Terbinafin

    9. Terbinex

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

    11. Terbinafina

    12. (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalene Methanamine

    13. Terbinafine Free Base

    14. Tdt-067

    15. G7riw8s0xp

    16. Chembl822

    17. Chebi:9448

    18. Lamisil Tablet

    19. 91161-71-6 (free Base)

    20. Terbinafinum

    21. Zabel

    22. 1-naphthalenemethanamine, N-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-, (e)-

    23. Ncgc00159346-02

    24. (2e)-n,6,6-trimethyl-n-(1-naphthylmethyl)hept-2-en-4-yn-1-amine

    25. (2e)-n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine

    26. Dsstox_cid_3640

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

    28. Dsstox_rid_77123

    29. Dsstox_gsid_23640

    30. Lamasil (tn)

    31. Cas-91161-71-6

    32. Unii-g7riw8s0xp

    33. Terbinafine (usan/inn)

    34. Brn 4256376

    35. Corbinal

    36. Terbinafine [usan:inn:ban]

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

    38. Erbinafine Hydrochloride

    39. Terbinafine [mi]

    40. Terbinafine, Sf-86-327, Lamisil, Tbnf

    41. Terbinafine [inn]

    42. Terbinafine [usan]

    43. Ec 618-706-8

    44. Terbinafine [vandf]

    45. Terbinafine [mart.]

    46. Schembl36794

    47. Schembl37843

    48. Terbinafine [who-dd]

    49. Mls006011885

    50. Bidd:gt0825

    51. Dtxsid2023640

    52. Terbinafine (lamisil, Terbinex)

    53. Terbinafine [green Book]

    54. Chebi:94705

    55. Terbinafine [orange Book]

    56. Hms2089b20

    57. Hms3715l08

    58. Albb-027269

    59. Bcp22896

    60. Osurnia Component Terbinafine

    61. Zinc1530981

    62. Tox21_111591

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

    64. Bbl010959

    65. Bdbm50018518

    66. Hy-17395a

    67. Mfcd00242672

    68. S1725

    69. Stk802069

    70. Akos001451917

    71. Tox21_111591_1

    72. Ac-8561

    73. Ccg-221253

    74. Cs-1944

    75. Db00857

    76. Gs-3099

    77. Terbinafine Component Of Osurnia

    78. (e)-n,6,6-trimethyl-n-(naphthalen-1

    79. Ncgc00159346-03

    80. Ncgc00159346-04

    81. Ncgc00188975-01

    82. Terbinafine [ema Epar Veterinary]

    83. Sf86-327

    84. Smr004703509

    85. Sbi-0206829.p001

    86. Sw197656-3

    87. T3677

    88. C08079

    89. D02375

    90. Ab00698510-07

    91. Ab00698510-09

    92. Ab00698510-10

    93. Ab00698510-11

    94. Ab00698510_12

    95. Ab00698510_13

    96. Ab00698510_14

    97. 161t716

    98. A843743

    99. Q415259

    100. Brd-k68132782-003-05-4

    101. (6,6-dimethyl-hept-2-en-4-ynyl)-methyl-naphthalen-1-ylmethyl-amine

    102. N,6,6-trimethyl-n-(1-naphthylmethyl)-2-heptene-4-yne-1-amine

    103. Sf 86-327; Sf-86-327; Sf86-327; Lamasil; Lamisil At

    104. ((e)-6,6-dimethyl-hept-2-en-4-ynyl)-methyl-naphthalen-1-ylmethyl-amine

    105. 1n,6,6-trimethyl-1n-(1-naphthylmethyl)-(e)-2-hepten-4-yn-1-amine

    106. (6,6-dimethyl-hept-2-en-4-ynyl)-methyl-naphthalen-1-ylmethyl-amine(terbinafine)

    107. (6,6-dimethylhept-2-en-4-yn-1-yl)methyl(1-naphthylmethyl)amine Hydrochloride

    108. [(2e)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)[(naphthalen-1-yl)methyl]amine

    109. [(e)-6,6-dimethyl-hept-2-en-4-ynyl]-methyl-(naphthalen-1-yl-methyl)-amine

    110. 1-naphthalenemethanamine, N-[(2e)-6,6-dimethyl-2-hepten-4-yn-1-yl]-n-methyl-

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 291.4 g/mol
    Molecular Formula C21H25N
    XLogP35.6
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count5
    Exact Mass291.198699802 g/mol
    Monoisotopic Mass291.198699802 g/mol
    Topological Polar Surface Area3.2 Ų
    Heavy Atom Count22
    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 Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameLamisil
    PubMed HealthTerbinafine
    Drug ClassesAntifungal
    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 4  
    Drug NameLamisil at
    Active IngredientTerbinafine hydrochloride; Terbinafine
    Dosage FormSpray; Gel; Solution
    RouteTopical
    Strength1%
    Market StatusOver the Counter
    CompanyNovartis

    3 of 4  
    Drug NameLamisil
    PubMed HealthTerbinafine
    Drug ClassesAntifungal
    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

    4 of 4  
    Drug NameLamisil at
    Active IngredientTerbinafine hydrochloride; Terbinafine
    Dosage FormSpray; Gel; Solution
    RouteTopical
    Strength1%
    Market StatusOver the Counter
    CompanyNovartis

    4.2 Drug Indication

    Terbinafine hydrochloride is indicated to treat fungal skin and nail infections caused by _Trichophyton_ species, _Microsporum canis_, _Epidermophyton floccosum_, and _Tinea_ species. Terbinafine hydrochloride also treats yeast infections of the skin caused by _Candida_ species and _Malassezia furfur_.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Terbinafine is an allylamine antifungal that inhibits squalene epoxidase (also known as squalene monooxygenase) to prevent the formation of ergosterol and cause an accumulation of squalene, weakening the cell wall of fungal cells. Terbinafine distributes into tissues and has a long terminal elimination half life, so the duration of action is long. Overdose with terbinafine is rare, even above the therapeutic dose, so the therapeutic index is wide. Patients taking oral terbinafine should have liver function tests performed prior to treatment to reduce the risk of liver injury.

    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.)

    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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TERBINAFINE
    5.3.2 FDA UNII
    G7RIW8S0XP
    5.3.3 Pharmacological Classes
    Allylamine [CS]; Allylamine Antifungal [EPC]
    5.4 ATC Code

    D - Dermatologicals

    D01 - Antifungals for dermatological use

    D01A - Antifungals for topical use

    D01AE - Other antifungals for topical use

    D01AE15 - Terbinafine

    D - Dermatologicals

    D01 - Antifungals for dermatological use

    D01B - Antifungals for systemic use

    D01BA - Antifungals for systemic use

    D01BA02 - Terbinafine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Oral terbinafine is >70% absorbed but only 40% bioavailable after first pass metabolism, reaching a Cmax of 1g/mL with a Tmax of 2 hours an an AUC of 4.56g\*h/mL. Over the course of a week, 1% topical terbinafine's Cmax increases from 949-1049ng/cm2 and the AUC increases from 9694-13,492ng/cm2/h.

    Route of Elimination

    Terbinafine is approximately 80% eliminated in urine, while the remainder is eliminated in feces. The unmetabolized parent drug is not present in urine.

    Volume of Distribution

    A single 250mg oral dose of terbinafine has a volume of distribution at steady state of 947.5L or 16.6L/kg.

    Clearance

    A single 250mg oral dose of terbinafine has a clearance of 76L/h or 1.11L/h/kg.

    5.6 Metabolism/Metabolites

    Terbinafine can be deaminated to 1-naphthaldehyde by CYP2C9, 2B6, 2C8, 1A2, 3A4, and 2C19. 1-naphthaldehyde is then oxidized to 1-naphthoic acid or reduced to 1-naphthalenemethanol. Terbinafine can also be hydroxylated by CYP1A2, 2C9, 2C8, 2B6, and 2C19 to hydroxyterbinafine. Hydroxyterbinafine is then oxidized to carboxyterbinafine or N-demethylated by CYP3A4, 2B6, 1A2, 2C9, 2C8, and 2C19 to desmethylhydroxyterbinafine. Terbinafine can be N-demethylated to desmethylterbinafine. Desmethylterbinafine is then dihydroxylated to a desmethyldihydrodiol or hydroxylated to desmethylhydroxyterbinafine. Finally, terbinafine can be dihydroxylated to a dihydrodiol which is then N-demethylated to a desmethyldihydrodiol.

    Terbinafine has known human metabolites that include 1-Naphtaldehyde, Hydroxyterbinafine, and N-Desmethylterbinafine.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Oral terbinafine has an effective half life of approximately 36 hours. However, the terminal half life ranges from 200-400 hours as it distributes into skin and adipose tissue. 1% topical terbinafine's half life increases over the first seven days from approximately 10-40 hours.

    5.8 Mechanism of Action

    Terbinafine inhibits the enzyme squalene monooxygenase (also called squalene epoxidase), preventing the conversion of squalene to 2,3-oxydosqualene, a step in the synthesis of ergosterol. This inhibition leads to decreased ergosterol, which would normally be incorporated into the cell wall, and accumulation of squalene. Generation of a large number of squalene containing vesicles in the cytoplasm may leach other lipids away from, and further weaken, the cell wall.

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    05-Jan-2021
    31-Aug-2024
    KGS
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    (KGS)    		 Average Price
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