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    Tafluprost

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 452.5 g/mol
    Molecular Formula C25H34F2O5
    XLogP34.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count13
    Exact Mass452.23743050 g/mol
    Monoisotopic Mass452.23743050 g/mol
    Topological Polar Surface Area76 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity614
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    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 2  
    Drug NameZioptan
    PubMed HealthTafluprost (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelTafluprost 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 IngredientTafluprost
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.0015%
    Market StatusPrescription
    CompanyOak Pharms

    2 of 2  
    Drug NameZioptan
    PubMed HealthTafluprost (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelTafluprost 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 IngredientTafluprost
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.0015%
    Market StatusPrescription
    CompanyOak 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.