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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]