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Chemistry

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Also known as: 65473-14-5, Naftifine hcl, Naftin, Exoderil, Naftifungin, Naftifine, hcl
Molecular Formula
C21H22ClN
Molecular Weight
323.9  g/mol
InChI Key
OLUNPKFOFGZHRT-YGCVIUNWSA-N
FDA UNII
25UR9N9041

NAFTIFINE HCL
Naftifine Hydrochloride is the hydrochloride salt form of naftifine, an allylamine derivate with synthetic broad-spectrum antifungal activity. Although the exact mechanism through which naftifine hydrochloride exerts its effect is unknown, it appears to selectively inhibit the enzyme squalene 2,3-epoxidase, thereby inhibiting the biosynthesis of sterol. This results in a decreased amount of sterols, especially ergosterol which is the primary fungal membrane sterol, and a corresponding accumulation of squalene in fungal cells. Naftifine hydrochloride can be fungicidal as well as fungistatic to yeasts depending on the concentration and the organisms involved.
1 2D Structure

NAFTIFINE HCL

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine;hydrochloride
2.1.2 InChI
InChI=1S/C21H21N.ClH/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20;/h2-15H,16-17H2,1H3;1H/b11-8+;
2.1.3 InChI Key
OLUNPKFOFGZHRT-YGCVIUNWSA-N
2.1.4 Canonical SMILES
CN(CC=CC1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32.Cl
2.1.5 Isomeric SMILES
CN(C/C=C/C1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32.Cl
2.2 Other Identifiers
2.2.1 UNII
25UR9N9041
2.3 Synonyms
2.3.1 MeSH Synonyms

1. N-cinnamyl-n-methyl-1-naphthalenemethylamine Hydrochloride

2. Naftifin

3. Naftifine

4. Naftifine Hydrochloride, (e)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 65473-14-5

2. Naftifine Hcl

3. Naftin

4. Exoderil

5. Naftifungin

6. Naftifine, Hcl

7. Aw 105-843

8. Naftifine (hydrochloride)

9. (e)-n-methyl-n-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine Hydrochloride

10. Aw 105843

11. Nsc-760068

12. Naft900

13. Chebi:7452

14. Naft-900

15. Naftifin

16. 25ur9n9041

17. N-trans-cinnamyl-n-methyl-(1-naphthylmethyl)amine Hydrochloride

18. Dsstox_cid_25496

19. Dsstox_rid_80915

20. Dsstox_gsid_45496

21. Aw-105-843

22. 65473-14-5 (hcl); 65472-88-0 (free Base).

23. (e)-n-methyl-n-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine;hydrochloride

24. Naftifinehydrochloride

25. Naftifine Hydrochloride [usan]

26. Suadian

27. Sn 105843

28. Unii-25ur9n9041

29. (e)-naftifine

30. Naftin Hydrochloride

31. Naftifine Hydrochloride [usan:usp]

32. Mfcd00059047

33. Naftin (tn)

34. (e)-n-methyl-n-(1-naphthylmethyl)-3-phenyl-prop-2-en-1-amine

35. (e)-n-cinnamyl-n-methyl-1-naphthalenemethylamine Hydrochloride

36. Ncgc00016908-01

37. (e)-n-methyl-n-(1-naphthylmethyl)-3-phenyl-2-propen-1-amine- Hydrochloride

38. Cas-65473-14-5

39. Surecn1649698

40. Schembl41356

41. Mls002154136

42. Naftifine Hydrochloride ,(s)

43. Naftifine Hydrochloride (usp)

44. Naft-600

45. Schembl4932462

46. Chembl1200493

47. Dtxsid2045496

48. Hy-b0518a

49. Hms1571e08

50. Pharmakon1600-01505446

51. Bcp07446

52. Naftifine Hydrochloride [mi]

53. Tox21_110677

54. Nsc760068

55. S3156

56. Akos015895211

57. Tox21_110677_1

58. Ac-1120

59. Ccg-213447

60. H72n880

61. Naftifine Hydrochloride [mart.]

62. Naftifine Hydrochloride [vandf]

63. Nsc 760068

64. 1-naphthalenemethanamine, N-methyl-n-(3-phenyl-2-propenyl)-, Hydrochloride, (e)-

65. 1-naphthalenemethanamine, N-methyl-n-[(2e)-3-phenyl-2-propenyl]-,hydrochloride

66. Naftifine Hydrochloride [usp-rs]

67. Naftifine Hydrochloride [who-dd]

68. Ncgc00179332-03

69. As-13296

70. Smr001233443

71. Sn-105843

72. C1162

73. Naftifine Hydrochloride [orange Book]

74. Naftifine Hydrochloride [usp Impurity]

75. C08072

76. D00883

77. Naftifine Hydrochloride [usp Monograph]

78. A835130

79. Sr-01000838853

80. Sr-01000838853-2

81. Naftifine Hydrochloride 100 Microg/ml In Acetonitrile

82. Q27107497

83. (e)-n-cinnamyl-n-methyl(1-naphthylmethyl)amine Hydrochloride

84. N-methyl-n-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine Hydrochloride

85. Naftifine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

86. (e)-n-methyl-n-(1-naphthalenylmethyl)-3-phenyl-2-propen-1-amine Hydrochloride

87. (e)-n-methyl-n-(3-phenyl-2-propenyl)-1-naphthalenemethanamine Hydrochloride

88. (e)-n-methyl-n-(naphthalen-1-ylmethyl)-3-phenyl-prop-2-en-1-amine Hydrochloride

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 323.9 g/mol
Molecular Formula C21H22ClN
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count5
Exact Mass323.1440774 g/mol
Monoisotopic Mass323.1440774 g/mol
Topological Polar Surface Area3.2 Ų
Heavy Atom Count23
Formal Charge0
Complexity342
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 2  
Drug NameNaftin
PubMed HealthNaftifine (On the skin)
Drug ClassesAntifungal
Drug LabelNaftin Cream, 1% contains the synthetic, broad-spectrum, antifungal agent naftifine hydrochloride. Naftin Cream, 1% is for topical use only....
Active IngredientNaftifine hydrochloride
Dosage FormCream; Gel
RouteTopical
Strength1%; 2%
Market StatusPrescription
CompanyMerz Pharms

2 of 2  
Drug NameNaftin
PubMed HealthNaftifine (On the skin)
Drug ClassesAntifungal
Drug LabelNaftin Cream, 1% contains the synthetic, broad-spectrum, antifungal agent naftifine hydrochloride. Naftin Cream, 1% is for topical use only....
Active IngredientNaftifine hydrochloride
Dosage FormCream; Gel
RouteTopical
Strength1%; 2%
Market StatusPrescription
CompanyMerz Pharms

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.)


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

DRUG PRODUCT COMPOSITIONS

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DOSAGE - GEL;TOPICAL - 1%

USFDA APPLICATION NUMBER - 19356

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DOSAGE - CREAM;TOPICAL - 1% **Federal Registe...DOSAGE - CREAM;TOPICAL - 1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19599

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DOSAGE - CREAM;TOPICAL - 2%

USFDA APPLICATION NUMBER - 19599

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DOSAGE - GEL;TOPICAL - 2%

USFDA APPLICATION NUMBER - 204286

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