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Tafluprost

Synopsis, Chemistry

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Also known as: 209860-87-7, Afp-168, Taflotan, Zioptan, Saflutan, Mk-2452

Molecular Formula

C₂₅H₃₄F₂O₅

Molecular Weight

452.5 g/mol

InChI Key

WSNODXPBBALQOF-VEJSHDCNSA-N

FDA UNII

1O6WQ6T7G3

A prostaglandin analogue ester prodrug used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Chemically, tafluprost is a fluorinated analog of prostaglandin F2-alpha. Tafluprost was approved for use in the U.S. on February 10, 2012.

Tafluprost is a Prostaglandin Analog. The mechanism of action of tafluprost is as a Prostaglandin Receptor Agonist. The physiologic effect of tafluprost is by means of Increased Prostaglandin Activity.

1 2D Structure

Tafluprost

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate

2.1.2 InChI

InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1

2.1.3 InChI Key

WSNODXPBBALQOF-VEJSHDCNSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

1O6WQ6T7G3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-methylethyl (5z)-7-((1r,2r, 3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy -1-butenyl)-3,5-dihydroxycyclopentyl)-5-heptenoate

2. Afp-168

2.3.2 Depositor-Supplied Synonyms

1. 209860-87-7

2. Afp-168

3. Taflotan

4. Zioptan

5. Saflutan

6. Mk-2452

7. 1o6wq6t7g3

8. Chebi:66899

9. Mk2452

10. (z)-isopropyl 7-((1r,2r,3r,5s)-2-((e)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate

11. Tapros

12. Isopropyl (5z)-7-{(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate

13. Propan-2-yl (5z)-7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate

14. Propan-2-yl (z)-7-[(1r,2r,3r,5s)-2-[(e)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate

15. Zioptan (tn)

16. Isopropyl (5z)-7-((1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoate

17. Isopropyl (5z)-7-{(1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl}hept-5-enoate

18. Tafluprost [inn]

19. Tafluprost [mi]

20. Tafluprost [jan]

21. Tafluprost [inci]

22. Tafluprost [usan]

23. Tafluprost [vandf]

24. Tafluprost [mart.]

25. Tafluprost [who-dd]

26. Unii-1o6wq6t7g3

27. Tafluprost (jan/usan/inn)

28. Tafluprost [usan:inn:ban]

29. Gtpl7451

30. Schembl1286148

31. Chembl1963683

32. Tafluprost [orange Book]

33. Ex-a564

34. Dtxsid401021504

35. Hms3649f04

36. Mk2452afp-168

37. Hy-b0600

38. De-085

39. De-118

40. S4851

41. Zinc13912394

42. Akos025294885

43. Ccg-269257

44. Db08819

45. As-75193

46. D06274

47. 860t877

48. Sr-01000946707

49. J-502635

50. Q2139543

51. Sr-01000946707-1

52. (z)-isopropyl 7-((1r,2r,3r,5s)-2-((e)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxy Cyclopentyl)hept-5-enoate

53. (z)-isopropyl7-((1r,2r,3r,5s)-2-((e)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate

54. 1-methylethyl (5-z)-7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoate

55. 1-methylethyl (5z)-7-((1r,2r, 3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy -1-butenyl-3,5-dihydroxycyclopentyl)-5-heptenoate

56. 1-methylethyl (5z)-7-{(1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5- Dihydroxycyclopentyl}hept-5-enoate

57. 5-heptenoic Acid, 7-((1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy-1-buten-1-yl)-3,5- Dihydroxycyclopentyl)-, 1-methylethyl Ester, (5z)-

58. 5-heptenoic Acid, 7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl Ester, (5z)-

59. 5-heptenoic Acid, 7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxy-1-butenyl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl Ester, (5z)-

60. Propan-2-yl (z)-7-[(1r,2r,3r,5s)-2-[(e)-3,3-difluoro-4-(phenoxy)but-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₄F₂O₅
Molecular Weight	452.5 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	13
Exact Mass	452.23743050 g/mol
Monoisotopic Mass	452.23743050 g/mol
Topological Polar Surface Area	76 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	614
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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 2
Drug Name	Zioptan
PubMed Health	Tafluprost (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Tafluprost is a fluorinated analog of prostaglandin F2. The chemical name for tafluprost is 1-methylethyl (5Z)-7-{(1R, 2R, 3R, 5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-butenyl}-3,5-dihydroxycyclopentyl]-5-heptenoate. The molecular formula of tafluprost...
Active Ingredient	Tafluprost
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.0015%
Market Status	Prescription
Company	Oak Pharms

2 of 2
Drug Name	Zioptan
PubMed Health	Tafluprost (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Tafluprost is a fluorinated analog of prostaglandin F2. The chemical name for tafluprost is 1-methylethyl (5Z)-7-{(1R, 2R, 3R, 5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-butenyl}-3,5-dihydroxycyclopentyl]-5-heptenoate. The molecular formula of tafluprost...
Active Ingredient	Tafluprost
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.0015%
Market Status	Prescription
Company	Oak Pharms

4.2 Drug Indication

Tafluprost is indicated for reducing elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

FDA Label

Treatment of glaucoma

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tafluprost is a novel prostaglandin analog with a high affinity for the fluoroprostaglandin (FP) receptor PGF2. Tafluprost has an affinity for the FP receptor that is approximately 12 times higher than that of the carboxylic acid of latanoprost, but with almost no potential to bind to other receptors.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

TAFLUPROST

5.2.2 FDA UNII

1O6WQ6T7G3

5.2.3 Pharmacological Classes

Prostaglandin Analog [EPC]; Prostaglandin Receptor Agonists [MoA]; Prostaglandins [CS]; Increased Prostaglandin Activity [PE]

5.3 ATC Code

S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EE - Prostaglandin analogues

S01EE05 - Tafluprost

5.4 Absorption, Distribution and Excretion

Absorption

Following instillation, tafluprost is absorbed through the cornea and is hydrolyzed to the biologically active acid metabolite, tafluprost acid. Tafluprost is an ester which makes the drug lipophillic enough to be quickly absorbed through. When administered to the eye, the peak plasma concentration (Cmax) and time to peak plasma concentration (Tmax) of tafluprost acid in healthy subjects was 26 pg/mL and 10 minutes respectively. a AUC, tafluprost acid = 394 pg*min/mL - 432 pg*min/mL.

Route of Elimination

Mean plasma tafluprost acid concentrations were below the limit of quantification of the bioanalytical assay (10 pg/mL) at 30 minutes following topical ocular administration of tafluprost 0.0015% ophthalmic solution. In male rats, it was observed that tafluprost was excreted into the feces.

Volume of Distribution

The highest concentration of tafluprost acid was found in the cornea and conjunctiva.

5.5 Metabolism/Metabolites

Tafluprost is an ester prodrug which is rapidly hydrolyzed by corneal esterases to form its biologically active acid metabolite. Tafluprost acid is further metabolized via fatty acid -oxidation and phase II conjugation into 1,2,3,4-tetranor acid.

5.6 Mechanism of Action

Tafluprost acid is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and humans suggest that the main mechanism of action is increased uveoscleral outflow.