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    NAFTIFINE HCL

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    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

    2D Structure

    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]