List of Drug Master Files (DMF) of Travoprost Active Pharmaceutical Ingredient listed on PharmaCompass.com

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Synopsis

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

Travoprost
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 Weight 500.5 g/mol
Molecular Formula C26H35F3O6
XLogP34.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count13
Exact Mass500.23857332 g/mol
Monoisotopic Mass500.23857332 g/mol
Topological Polar Surface Area96.2 Ų
Heavy Atom Count35
Formal Charge0
Complexity693
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameTravatan z
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost 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 IngredientTravoprost
Dosage FormSolution/drops
RouteOphthalmic
Strength0.004%
Market StatusPrescription
CompanyAlcon Pharms

2 of 4  
Drug NameTravoprost
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost 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 IngredientTravoprost
Dosage FormSolution/drops; Solution
RouteOphthalmic; ophthalmic
Strength0.004%
Market StatusTentative Approval; Prescription
CompanyPar Pharm

3 of 4  
Drug NameTravatan z
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost 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 IngredientTravoprost
Dosage FormSolution/drops
RouteOphthalmic
Strength0.004%
Market StatusPrescription
CompanyAlcon Pharms

4 of 4  
Drug NameTravoprost
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost 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 IngredientTravoprost
Dosage FormSolution/drops; Solution
RouteOphthalmic; ophthalmic
Strength0.004%
Market StatusTentative Approval; Prescription
CompanyPar 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


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.


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"}]
04-Feb-2021
13-Aug-2024
GMS
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