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Naftifine

Naftifine

Synopsis, Chemistry

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GEL;TOPICAL - 1%, CREAM;TOPICAL - 1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CREAM;TOPICAL - 2%, GEL;TOPICAL - 2%

GEL;TOPICAL - 1%
CREAM;TOPICAL - 1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
CREAM;TOPICAL - 2%
GEL;TOPICAL - 2%

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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 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

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 Formula	C₂₁H₂₂ClN
Molecular Weight	323.9 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	5
Exact Mass	323.1440774 g/mol
Monoisotopic Mass	323.1440774 g/mol
Topological Polar Surface Area	3.2 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	342
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 2
Drug Name	Naftin
PubMed Health	Naftifine (On the skin)
Drug Classes	Antifungal
Drug Label	Naftin Cream, 1% contains the synthetic, broad-spectrum, antifungal agent naftifine hydrochloride. Naftin Cream, 1% is for topical use only....
Active Ingredient	Naftifine hydrochloride
Dosage Form	Cream; Gel
Route	Topical
Strength	1%; 2%
Market Status	Prescription
Company	Merz Pharms

2 of 2
Drug Name	Naftin
PubMed Health	Naftifine (On the skin)
Drug Classes	Antifungal
Drug Label	Naftin Cream, 1% contains the synthetic, broad-spectrum, antifungal agent naftifine hydrochloride. Naftin Cream, 1% is for topical use only....
Active Ingredient	Naftifine hydrochloride
Dosage Form	Cream; Gel
Route	Topical
Strength	1%; 2%
Market Status	Prescription
Company	Merz 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]