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MolPort-001-758-011

MolPort-001-758-011

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

62 API Suppliers, 27 USDMF, 23 CEP/COS, 17 JDMF, 14 EU WC, 36 KDMF, 27 NDC API, 29 Listed Suppliers

DEVELOPMENTS

4 Drug(s) in Development

4 Drug(s) in Development

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INTERMEDIATES

7 Suppliers

7 Suppliers

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122 Dossiers, 25 FDA Orange Book, 53 Europe, 10 Canada, 14 South Africa, 20 Listed Dossiers

DRUG PRODUCT COMPOSITION

TABLET;ORAL - EQ 250MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CREAM;TOPICAL - 1%, SOLUTION;TOPICAL - 1%, GRANULE;ORAL - EQ 125MG BASE/PACKET, GRANULE;ORAL - EQ 187.5MG BASE/PACKET

TABLET;ORAL - EQ 250MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
CREAM;TOPICAL - 1%
SOLUTION;TOPICAL - 1%
GRANULE;ORAL - EQ 125MG BASE/PACKET
GRANULE;ORAL - EQ 187.5MG BASE/PACKET

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43 Coating Systems & Additives, 27 Controlled & Modified Release, 25 Disintegrants & Superdisintegrants, 25 Fillers, Diluents & Binders, 21 Topical, 18 Thickeners and Stabilizers, 15 Solubilizers, 15 Direct Compression, 14 Granulation, 14 Lubricants & Glidants, 7 Film Formers & Plasticizers, 7 Emulsifying Agents, 6 Co-Processed Excipients, 6 Taste Masking, 6 Parenteral, 5 Empty Capsules, 4 Vegetarian Capsules, 4 API Stability Enhancers, 3 Surfactant & Foaming Agents, 3 Rheology Modifiers, 3 Chewable & Orodispersible Aids, 2 Coloring Agents

GLOBAL SALES INFORMATION

9 US Medicaid Prescriptions, 19 Finished Drug Prices

MARKET PLACE

14 APIs

14 APIs

PATENTS

5 Health Canada Patents

5 Health Canada Patents

ANALYTICAL SOLUTION(s)

1 BioAnalytical Methods, 2 EDQM Standards, 1 USP Standards, 2 Other Ref. Standards

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1 Data Compilations & Company Tracker #PharmaFlow, 2 News

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150

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USA (Orange Book)

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49.00

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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

A naphthalene derivative that inhibits fungal SQUALENE EPOXIDASE and is used to treat DERMATOMYCOSES of the skin and nails.

1 2D Structure

MolPort-001-758-011

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 Formula	C₂₁H₂₆ClN
Molecular Weight	327.9 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	5
Exact Mass	327.1753775 g/mol
Monoisotopic Mass	327.1753775 g/mol
Topological Polar Surface Area	3.2 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	428
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Lamisil
Drug Label	Lamisil 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 Ingredient	Terbinafine hydrochloride
Dosage Form	Tablet; Cream; Granule
Route	Oral; Topical
Strength	eq 187.5mg base/packet; 1%; eq 250mg base; eq 125mg base/packet
Market Status	Over the Counter; Prescription
Company	Novartis

2 of 6
Drug Name	Lamisil at
Active Ingredient	Terbinafine hydrochloride; Terbinafine
Dosage Form	Spray; Gel; Solution
Route	Topical
Strength	1%
Market Status	Over the Counter
Company	Novartis

3 of 6
Drug Name	Terbinafine hydrochloride
PubMed Health	Terbinafine
Drug Classes	Antifungal
Drug Label	Terbinafine 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 Ingredient	Terbinafine hydrochloride
Dosage Form	Tablet; Cream
Route	oral; Oral; Topical
Strength	1%; eq 250mg base
Market Status	Tentative Approval; Over the Counter; Prescription
Company	Wockhardt; 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 Name	Lamisil
Drug Label	Lamisil 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 Ingredient	Terbinafine hydrochloride
Dosage Form	Tablet; Cream; Granule
Route	Oral; Topical
Strength	eq 187.5mg base/packet; 1%; eq 250mg base; eq 125mg base/packet
Market Status	Over the Counter; Prescription
Company	Novartis

5 of 6
Drug Name	Lamisil at
Active Ingredient	Terbinafine hydrochloride; Terbinafine
Dosage Form	Spray; Gel; Solution
Route	Topical
Strength	1%
Market Status	Over the Counter
Company	Novartis

6 of 6
Drug Name	Terbinafine hydrochloride
PubMed Health	Terbinafine
Drug Classes	Antifungal
Drug Label	Terbinafine 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 Ingredient	Terbinafine hydrochloride
Dosage Form	Tablet; Cream
Route	oral; Oral; Topical
Strength	1%; eq 250mg base
Market Status	Tentative Approval; Over the Counter; Prescription
Company	Wockhardt; 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]