Find Terconazole manufacturers, exporters & distributors on PharmaCompass

Prestwick3_000495

Prestwick3_000495

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

12 API Suppliers, 6 USDMF, 1 CEP/COS, 1 EU WC, 3 NDC API, 5 Listed Suppliers

PRICE INFORMATION

API Reference Price, API Exports, API Imports

INTERMEDIATES

2 Suppliers

2 Suppliers

DOSSIERs // Finished Dosage Formulations

11 Dossiers, 10 FDA Orange Book, 1 Canada

DRUG PRODUCT COMPOSITION

CREAM;VAGINAL - 0.4% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, SUPPOSITORY;VAGINAL - 80MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CREAM;VAGINAL - 0.8% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CREAM;VAGINAL - 0.8%

CREAM;VAGINAL - 0.4% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
SUPPOSITORY;VAGINAL - 80MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
CREAM;VAGINAL - 0.8% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
CREAM;VAGINAL - 0.8%

RELATED EXCIPIENT COMPANIES

Suppliers, 8 BASF, 7 Seppic, 4 Gangwal Chemicals, 3 Nanjing Well Pharmaceutical, 2 Actylis, 1 Jai Radhe Sales, 1 Nanjing Bold Chemical, 1 Finar

EXCIPIENTS BY APPLICATIONS

15 Solubilizers, 11 Topical, 6 Parenteral, 4 Emulsifying Agents, 3 Surfactant & Foaming Agents, 3 Thickeners and Stabilizers, 3 Film Formers & Plasticizers, 2 Direct Compression, 1 Fillers, Diluents & Binders, 1 Rheology Modifiers, 1 API Stability Enhancers, 1 Lubricants & Glidants, 1 Granulation, 1 Co-Processed Excipients

GLOBAL SALES INFORMATION

11 US Medicaid Prescriptions, 1 Finished Drug Prices

MARKET PLACE

6 APIs

6 APIs

ANALYTICAL SOLUTION(s)

2 EDQM Standards, 1 USP Standards, 1 Other Ref. Standards

Product Search

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

Other Certificates

Other Suppliers

API REF. PRICE (USD / KG)

813

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

38.00

Annual Reports

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

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

Prestwick3_000495

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 Formula	C₂₆H₃₁Cl₂N₅O₃
Molecular Weight	532.5 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	531.1803953 g/mol
Monoisotopic Mass	531.1803953 g/mol
Topological Polar Surface Area	64.9 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	693
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Terazol 3
Drug Label	TERAZOL 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 Ingredient	Terconazole
Dosage Form	Cream; Suppository
Route	Vaginal
Strength	0.8%; 80mg
Market Status	Prescription
Company	Janssen Pharms

2 of 6
Drug Name	Terazol 7
PubMed Health	Terconazole (Vaginal)
Drug Classes	Antifungal
Drug Label	TERAZOL 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 Ingredient	Terconazole
Dosage Form	Cream
Route	Vaginal
Strength	0.4%
Market Status	Prescription
Company	Janssen Pharms

3 of 6
Drug Name	Terconazole
PubMed Health	Terconazole (Vaginal)
Drug Classes	Antifungal
Drug Label	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-dioxolan-4-yl]met...
Active Ingredient	Terconazole
Dosage Form	Cream; Suppository
Route	Vaginal
Strength	0.4%; 0.8%; 80mg
Market Status	Prescription
Company	Nycomed Us; Taro; Fougera Pharms; Perrigo New York

4 of 6
Drug Name	Terazol 3
Drug Label	TERAZOL 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 Ingredient	Terconazole
Dosage Form	Cream; Suppository
Route	Vaginal
Strength	0.8%; 80mg
Market Status	Prescription
Company	Janssen Pharms

5 of 6
Drug Name	Terazol 7
PubMed Health	Terconazole (Vaginal)
Drug Classes	Antifungal
Drug Label	TERAZOL 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 Ingredient	Terconazole
Dosage Form	Cream
Route	Vaginal
Strength	0.4%
Market Status	Prescription
Company	Janssen Pharms

6 of 6
Drug Name	Terconazole
PubMed Health	Terconazole (Vaginal)
Drug Classes	Antifungal
Drug Label	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-dioxolan-4-yl]met...
Active Ingredient	Terconazole
Dosage Form	Cream; Suppository
Route	Vaginal
Strength	0.4%; 0.8%; 80mg
Market Status	Prescription
Company	Nycomed 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.