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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
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

Terconazole

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.


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12-Jan-2021
20-Sep-2024
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CREAM;VAGINAL - 0.4% **Federal Regis...DOSAGE - CREAM;VAGINAL - 0.4% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19579

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DOSAGE - SUPPOSITORY;VAGINAL - 80MG **Federal...DOSAGE - SUPPOSITORY;VAGINAL - 80MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19641

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DOSAGE - CREAM;VAGINAL - 0.8% **Federal Regis...DOSAGE - CREAM;VAGINAL - 0.8% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19964

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DOSAGE - CREAM;VAGINAL - 0.8%

USFDA APPLICATION NUMBER - 21735

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