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Travoprost

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85 FDF Dossiers, 12 FDA Orange Book, 49 Europe, 7 Canada, 2 Australia, 3 South Africa, 12 Listed Dossiers

85 FDF Dossiers
12 FDA Orange Book
49 Europe
7 Canada
2 Australia
3 South Africa
12 Listed Dossiers

RELATED EXCIPIENT COMPANIES

2 Rochem International Inc, 13 SPI Pharma, 1 DKSH, 1 Gangwal Healthcare, 4 Nanjing Well Pharmaceutical, 2 Pfanstiehl, 3 Actylis, 3 BASF, 1 BioSpectra, 1 Corel Pharma Chem, 2 Finar, 3 Gangwal Chemicals, 1 Ingredion Pharma Solutions, 2 Kerry, 2 Microlex e.U, 1 Pluviaendo, 14 Roquette, 1 Seppic, 1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 2 Shijiazhuang Huaxu Pharmaceutical, 1 Sigachi Industries, 2 Valens Pharmachem, 1 Zhejiang Huakang Pharmaceutical

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20 Fillers, Diluents & Binders
13 Parenteral
12 Taste Masking
12 Film Formers & Plasticizers
11 Chewable & Orodispersible Aids
10 Direct Compression
9 Solubilizers
7 Topical
4 Co-Processed Excipients
4 Coating Systems & Additives
4 Granulation
3 Emulsifying Agents
3 Thickeners and Stabilizers
3 Disintegrants & Superdisintegrants
2 API Stability Enhancers
1 Soft Gelatin
1 Surfactant & Foaming Agents

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1 DATA COMPILATION #PharmaFlow, 13 NEWS #PharmaBuzz

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GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions, 39 Finished Drug Prices, 1 Annual Reports

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39 Finished Drug Prices
1 Annual Reports

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2 FDF Dossiers

PATENTS & EXCLUSIVITIES

9 US Patents, 1 US Exclusivities, 6 Health Canada Patents

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9 US Patents
1 US Exclusivities
6 Health Canada Patents

REF. STANDARDS & IMPURITIES

2 USP , 2 Others

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2 USP
2 Others

Cayman Travoprost

Synopsis

Chemistry

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Also known as: 157283-68-6, Travatan, Travatan z, Izba, Al-6221, Travaprost

Molecular Formula

C₂₆H₃₅F₃O₆

Molecular Weight

500.5 g/mol

InChI Key

MKPLKVHSHYCHOC-AHTXBMBWSA-N

FDA UNII

WJ68R08KX9

A cloprostenol derivative that is used as an ANTIHYPERTENSIVE AGENT in the treatment of OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.

Travoprost is a Prostaglandin Analog.

1 2D Structure

Travoprost

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate

2.1.2 InChI

InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1

2.1.3 InChI Key

MKPLKVHSHYCHOC-AHTXBMBWSA-N

2.1.4 Canonical SMILES

CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC=CC(=C2)C(F)(F)F)O)O)O

2.1.5 Isomeric SMILES

CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](COC2=CC=CC(=C2)C(F)(F)F)O)O)O

2.2 Other Identifiers

2.2.1 UNII

WJ68R08KX9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (((1r)-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

2. Al 6221

3. Al-6221

4. Al6221

5. Travatan

6. Travatan Z

7. Z, Travatan

2.3.2 Depositor-Supplied Synonyms

1. 157283-68-6

2. Travatan

3. Travatan Z

4. Izba

5. Al-6221

6. Travaprost

7. Trovoprost

8. Otx-tp

9. Chebi:746859

10. Propan-2-yl (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate

11. Al6221

12. Wj68r08kx9

13. Nsc-760366

14. Travoprost [usan]

15. Travatanz

16. (z)-isopropyl 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r,e)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

17. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-{(1e,3r)-3-hydroxy-4-[(alpha,alpha,alpha-trifluoro-m-tolyl)oxy]-1-butenyl}cyclopentyl)-5-heptenoate

18. Travatan (tn)

19. 5-heptenoic Acid, 7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-, 1-methylethyl Ester, (5z)-

20. Propan-2-yl (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate

21. Propan-2-yl (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-{(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl}cyclopentyl]hept-5-enoate

22. Travoprostum

23. Unii-wj68r08kx9

24. (((1r)-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

25. (+)-fluprostenol Isopropyl Ester

26. Travoprost [usan:usp:inn:ban]

27. Travoprost In Bulk

28. Travoprostintermediates

29. Travoprost [mi]

30. Travoprost [inn]

31. Travoprost [jan]

32. Travoprost [vandf]

33. Travoprost [mart.]

34. Travoprost [usp-rs]

35. Travoprost [who-dd]

36. Schembl93818

37. Travoprost (jan/usp/inn)

38. (1r-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

39. (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3r)-3-hydroxy-4-((alpha,alpha,alpha-trifluoro-m-isopropyl-tolyl)oxy)-1-butenyl)cyclopentyl)-5-heptenoate

40. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl Ester, (1r-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-

41. Travoprost [ema Epar]

42. Gtpl7102

43. Chembl1200799

44. Travoprost [orange Book]

45. Dtxsid80896948

46. Travoprost [usp Monograph]

47. Duotrav Component Travoprost

48. Ex-a1772

49. Hy-b0584

50. Zinc4474682

51. Bdbm50248302

52. S3738

53. Akos024458039

54. Travoprost Component Of Duotrav

55. Ac-6103

56. Am84515

57. Ccg-269692

58. Db00287

59. Nsc 760366

60. Ncgc00346741-02

61. 5-heptenoic Acid, 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3r)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl Ester, (5z)-

62. Bs-15509

63. Fluprostenol Isopropyl Ester;al6221;flu-ipr

64. D01964

65. 283t686

66. Sr-01000942266

67. Sr-01000946860

68. J-502633

69. Q2193376

70. Sr-01000942266-1

71. Sr-01000946860-1

72. Fluprostenol Isopropyl Ester, >=98%, Ethanol Solution

73. (1r-(1.alpha.(z),2.beta.(1e,3r*),3.alpha.,5.alpha.))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

74. (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-5-heptenoic Acid 1-methyethyl Ester

75. (z)-isopropyl 7-((1r,2r)-3,5-dihydroxy-2-((s,e)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

76. (z)-isopropyl 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r,e)-3-hydroxy-4-(3-(trifluoromethyl) Phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

77. (z)-isopropyl7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r,e)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

78. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3r)-3-hydroxy-4-((.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy)-1-butenyl)cyclopentyl)-5-heptenoate

79. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((3r,e)-3-hydroxy-4-(3-(trifluoromethyl)-phenoxy)-but-1-enyl)-cyclopentyl)-hept-5-enoate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₅F₃O₆
Molecular Weight	500.5 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	13
Exact Mass	500.23857332 g/mol
Monoisotopic Mass	500.23857332 g/mol
Topological Polar Surface Area	96.2 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	693
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Travatan z
PubMed Health	Travoprost (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Travoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active Ingredient	Travoprost
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.004%
Market Status	Prescription
Company	Alcon Pharms

2 of 4
Drug Name	Travoprost
PubMed Health	Travoprost (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Travoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active Ingredient	Travoprost
Dosage Form	Solution/drops; Solution
Route	Ophthalmic; ophthalmic
Strength	0.004%
Market Status	Tentative Approval; Prescription
Company	Par Pharm

3 of 4
Drug Name	Travatan z
PubMed Health	Travoprost (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Travoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active Ingredient	Travoprost
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.004%
Market Status	Prescription
Company	Alcon Pharms

4 of 4
Drug Name	Travoprost
PubMed Health	Travoprost (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Travoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active Ingredient	Travoprost
Dosage Form	Solution/drops; Solution
Route	Ophthalmic; ophthalmic
Strength	0.004%
Market Status	Tentative Approval; Prescription
Company	Par Pharm

4.2 Drug Indication

Travoprost ophthalmic solution is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Travoprost is also currently indicated for the decrease of elevated intraocular pressure in paediatric patients aged 2 months to < 18 years with ocular hypertension or paediatric glaucoma.

FDA Label

Decrease of elevated intraocular pressure in adult patients with ocular hypertension or open-angle glaucoma (see section 5. 1). Decrease of elevated intraocular pressure in paediatric patients aged 3 years to < 18 years with ocular hypertension or paediatric glaucoma.

Decrease of elevated intraocular pressure in adult patients with ocular hypertension or open-angle glaucoma (see section 5. 1).

Decrease of elevated intraocular pressure in paediatric patients aged 2 months to < 18 years with ocular hypertension or paediatric glaucoma (see section 5. 1).

Treatment of glaucoma

5 Pharmacology and Biochemistry

5.1 Pharmacology

Travoprost, an isopropyl ester prodrug, is a synthetic prostaglandin F2 alpha analog that is rapidly hydrolyzed by esterases in the cornea to its biologically active free acid. The travoprost free acid is potent and highly selective for the FP prostanoid receptor.

5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

TRAVOPROST

5.3.2 FDA UNII

WJ68R08KX9

5.3.3 Pharmacological Classes

Prostaglandins [CS]; Prostaglandin Analog [EPC]

5.4 ATC Code

S01EE04

S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EE - Prostaglandin analogues

S01EE04 - Travoprost

5.5 Absorption, Distribution and Excretion

Absorption

Travoprost is systemically absorbed through the cornea. In humans, peak plasma concentrations of travoprost free acid were low (25 pg/mL or less) and occurred within 30 minutes following topical ocular administration of one drop of 0.004% travoprost ophthalmic solution.

Route of Elimination

Less than 2% of the topical ocular dose of travoprost was excreted in the urine within 4 hours as the travoprost free acid. Moreover, elimination from plasma is rapid, resulting in concentrations below the limit of quantitation (< 10 pg/mL) by one hour. Furthermore, in rats, 95% of a subcutaneous radiolabeled dose was eliminated within 24 hours. The major route of elimination was via the bile (61%) with the remainder excreted by the kidneys.

Volume of Distribution

Given the data currently available, it has been recorded that travoprost free acid is moderately distributed into body tissues with a volume of distribution of 2.6 L/kg in rats.

Clearance

Data regarding the clearance of travoprost is not readily available or accessible.

5.6 Metabolism/Metabolites

Travoprost, an isopropyl ester prodrug, is hydrolyzed by esterases in the cornea to its biologically active free acid. Systemically, travoprost free acid is rapidly and extensively metabolized in the kidney, liver, and lung to inactive metabolites via beta-oxidation of the α(carboxylic acid) chain to give the 1,2-dinor and 1,2,3,4-tetranor analogs, via oxidation of the 15-hydroxyl moiety, as well as via reduction of the 13,14 double bond.

5.7 Biological Half-Life

The terminal elimination half-life of travoprost free acid is determined to be approximately 45 minutes, although studies demonstrated half-life values that ranged from 17 to 86 minutes.

5.8 Mechanism of Action

Travoprost, a prostaglandin F2 analogue, is a highly selective full agonist which has a high affinity for the prostaglandin FP receptor, and facilitates reductions in intraocular pressure by increasing the outflow of aqueous humour via trabecular meshwork and uveoscleral pathways. Reduction of the intraocular pressure in man starts about 2 hours after administration and maximum effect is reached after 12 hours. Significant lowering of intraocular pressure can be maintained for periods exceeding 24 hours with a single dose.

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API Reference Price

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PRACE 657 27711 NERATOVICE 1 CZECH REPUBLIC Neratovice, NERATOVICE, CZECH REPUBLIC CZECH REPUBLIC","customerAddress":"304,MOHAN PLACE,L.S.C.BLOCK-C"}]

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14 Roquette

1 Seppic

1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

2 Shijiazhuang Huaxu Pharmaceutical

1 Sigachi Industries

2 Valens Pharmachem

1 Zhejiang Huakang Pharmaceutical

EXCIPIENTS BY APPLICATIONS

20 Fillers, Diluents & Binders

13 Parenteral

12 Taste Masking

12 Film Formers & Plasticizers

11 Chewable & Orodispersible Aids

10 Direct Compression

9 Solubilizers

7 Topical

4 Co-Processed Excipients

4 Coating Systems & Additives

4 Granulation

3 Emulsifying Agents

3 Thickeners and Stabilizers

3 Disintegrants & Superdisintegrants

2 API Stability Enhancers

1 Soft Gelatin

1 Surfactant & Foaming Agents

DIGITAL CONTENT

1 DATA COMPILATION #PharmaFlow

13 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions

39 Finished Drug Prices

1 Annual Reports

MARKET PLACE

11 APIs

2 FDF Dossiers

PATENTS & EXCLUSIVITIES

9 US Patents