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    Terconazole

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 67915-31-5, Triaconazole, Terazol 7, Gyno-terazol, Terazol 3, Fungistat
    Molecular Formula
    C26H31Cl2N5O3
    Molecular Weight
    532.5  g/mol
    InChI Key
    BLSQLHNBWJLIBQ-OZXSUGGESA-N
    Terconazole is a synthetic triazole derivative structurally related to fluconazole, antifungal Terconazole seems to disrupt cell wall synthesis by inhibiting biosynthesis of ergosterol or other sterols, damaging the fungal cell membrane, altering its permeability, and promoting loss of essential intracellular elements. Terconazole is active against Candida sp.. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-propan-2-ylpiperazine
    2.1.2 InChI
    InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1
    2.1.3 InChI Key
    BLSQLHNBWJLIBQ-OZXSUGGESA-N
    2.1.4 Canonical SMILES
    CC(C)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl
    2.1.5 Isomeric SMILES
    CC(C)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 1-(4-((2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazine

    2. Fungistat

    3. Gyno-terazol

    4. R 42470

    5. Terazol

    2.2.2 Depositor-Supplied Synonyms

    1. 67915-31-5

    2. Triaconazole

    3. Terazol 7

    4. Gyno-terazol

    5. Terazol 3

    6. Fungistat

    7. 1-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-propan-2-ylpiperazine

    8. Tercospor

    9. Chebi:82980

    10. Termayazole

    11. R 42470

    12. R-42470

    13. Panlomyc

    14. Nsc-331942

    15. Ncgc00016912-01

    16. Cas-67915-31-5

    17. Terazol 3 (tn)

    18. (2r,4s)-terconazole

    19. Terconazole (usp/inn)

    20. Prestwick3_000495

    21. Chembl1306

    22. Dsstox_cid_25498

    23. Dsstox_rid_80917

    24. Dsstox_gsid_45498

    25. Schembl23165

    26. Bspbio_000389

    27. Mls002153844

    28. Bidd:gt0705

    29. Bpbio1_000429

    30. Dtxsid2045498

    31. Hms2096d11

    32. Hms2233c22

    33. Hms3713d11

    34. Pharmakon1600-01503847

    35. Hy-b1790

    36. Zinc3873936

    37. Tox21_110679

    38. Bdbm50375318

    39. Mfcd05662369

    40. Nsc760361

    41. S5033

    42. Akos016846147

    43. Ccg-213216

    44. Cs-6456

    45. Db00251

    46. Ks-1463

    47. Nsc-760361

    48. Ncgc00179575-01

    49. As-14153

    50. Piperazine,1-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-(1-methylethyl)-, Rel-

    51. Smr001233206

    52. Ab00513849

    53. C08080

    54. C76152

    55. D00888

    56. Ab00513849_07

    57. 915t315

    58. A917374

    59. Sr-01000841196

    60. J-008500

    61. Q7701687

    62. Sr-01000841196-2

    63. Brd-k86204871-001-02-2

    64. Brd-k86204871-001-13-9

    65. 1-(4-(((2r,4s)-2-((1h-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-isopropylpiperazine

    66. 1-(4-{[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine

    67. 1-(4-{[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine

    68. 1-(4-{[(2r,4s)-2-(2,4-dichlorophenyl)-2-[(1h-1,2,4-triazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine

    69. 1-[4-[[(2r)-2alpha-(2,4-dichlorophenyl)-2beta-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4beta-yl]methoxy]phenyl]-4-(1-methylethyl)piperazine

    70. 1-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-propan-2-yl-piperazine

    71. 1h-pyrazole-3-acetamide,5-[[7-[3-[ethyl(2-hydroxyethyl)amino]propoxy]-4-quinazolinyl]amino]-n-(3-fluorophenyl)-

    2.3 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 532.5 g/mol
    Molecular Formula C26H31Cl2N5O3
    XLogP34.8
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass531.1803953 g/mol
    Monoisotopic Mass531.1803953 g/mol
    Topological Polar Surface Area64.9 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity693
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameTerazol 3
    Drug LabelTERAZOL 7 (terconazole) Vaginal Cream 0.4% is a white to off-white, water washable cream for intravaginal administration containing 0.4% of the antifungal agent terconazole, cis-1-[p-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-diox...
    Active IngredientTerconazole
    Dosage FormCream; Suppository
    RouteVaginal
    Strength0.8%; 80mg
    Market StatusPrescription
    CompanyJanssen Pharms

    2 of 6  
    Drug NameTerazol 7
    PubMed HealthTerconazole (Vaginal)
    Drug ClassesAntifungal
    Drug LabelTERAZOL 7 (terconazole) Vaginal Cream 0.4% is a white to off-white, water washable cream for intravaginal administration containing 0.4% of the antifungal agent terconazole, cis-1-[p-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-diox...
    Active IngredientTerconazole
    Dosage FormCream
    RouteVaginal
    Strength0.4%
    Market StatusPrescription
    CompanyJanssen Pharms

    3 of 6  
    Drug NameTerconazole
    PubMed HealthTerconazole (Vaginal)
    Drug ClassesAntifungal
    Drug LabelTerconazole vaginal cream 0.4% is a white to off-white, water washable cream for intravaginal administration containing 0.4% of the antifungal agent terconazole, cis-1-[p-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1 -ylmethyl)-1,3-dioxolan-4-yl]met...
    Active IngredientTerconazole
    Dosage FormCream; Suppository
    RouteVaginal
    Strength0.4%; 0.8%; 80mg
    Market StatusPrescription
    CompanyNycomed Us; Taro; Fougera Pharms; Perrigo New York

    4 of 6  
    Drug NameTerazol 3
    Drug LabelTERAZOL 7 (terconazole) Vaginal Cream 0.4% is a white to off-white, water washable cream for intravaginal administration containing 0.4% of the antifungal agent terconazole, cis-1-[p-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-diox...
    Active IngredientTerconazole
    Dosage FormCream; Suppository
    RouteVaginal
    Strength0.8%; 80mg
    Market StatusPrescription
    CompanyJanssen Pharms

    5 of 6  
    Drug NameTerazol 7
    PubMed HealthTerconazole (Vaginal)
    Drug ClassesAntifungal
    Drug LabelTERAZOL 7 (terconazole) Vaginal Cream 0.4% is a white to off-white, water washable cream for intravaginal administration containing 0.4% of the antifungal agent terconazole, cis-1-[p-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-diox...
    Active IngredientTerconazole
    Dosage FormCream
    RouteVaginal
    Strength0.4%
    Market StatusPrescription
    CompanyJanssen Pharms

    6 of 6  
    Drug NameTerconazole
    PubMed HealthTerconazole (Vaginal)
    Drug ClassesAntifungal
    Drug LabelTerconazole vaginal cream 0.4% is a white to off-white, water washable cream for intravaginal administration containing 0.4% of the antifungal agent terconazole, cis-1-[p-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1 -ylmethyl)-1,3-dioxolan-4-yl]met...
    Active IngredientTerconazole
    Dosage FormCream; Suppository
    RouteVaginal
    Strength0.4%; 0.8%; 80mg
    Market StatusPrescription
    CompanyNycomed Us; Taro; Fougera Pharms; Perrigo New York

    4.2 Drug Indication

    For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Terconazole is a triazole antifungal agent available for intravaginal use. It is structurally related to imidazole-derivative antifungal agents, although terconazole and other triazoles have 3 nitrogens in the azole ring. By inhibiting the 14-alpha-demethylase (lanosterol 14-alpha-demethylase), Terconazole inhibits ergosterol synthesis. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.

    5.2 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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Azoles [CS]; Azole Antifungal [EPC]
    5.4 ATC Code

    G - Genito urinary system and sex hormones

    G01 - Gynecological antiinfectives and antiseptics

    G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

    G01AG - Triazole derivatives

    G01AG02 - Terconazole

    5.5 Absorption, Distribution and Excretion

    Absorption

    Following intravaginal administration of terconazole in humans, absorption ranged from 5-8% in three hysterectomized subjects and 12-16% in two non-hysterectomized subjects with tubal ligations

    Route of Elimination

    Following oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.

    5.6 Metabolism/Metabolites

    Systemically absorbed drug appears to be rapidly and extensively metabolized. Terconazole primarily undergoes oxidatative N- and O-dealkylation, dioxolane ring cleavage, and conjugation.

    5.7 Biological Half-Life

    6.9 hours (range 4.0-11.3)

    5.8 Mechanism of Action

    Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 14-alpha-demethylase in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth.