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Tafluprost

July 24, 2017
Common Name

Tafluprost Description

Tafluprost is only found in individuals that have used or taken this drug. It is a prostaglandin analogue used topically (as eye drops) to control the progression of glaucoma and in the management of ocliar hypertension. Tafluprost was approved for use in the U.S. on February 10, 2012.Tafluprost is a prostaglandin F2a analogue. Specifically, Tafluprost is a prostanoid selective FP receptor agonist that is believed to reduce the intraocliar pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and man suggest that the main mechanism of action is increased uveoscleral outflow. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source ZioptanChEBI AFP-168HMDB SaflutanHMDB 1-Methylethyl (5Z)-7-((1R,2R, 3R,5S)-2-((1E)-3,3-difluoro-4-phenoxy -1-butenyl)-3,5-dihydroxycyclopentyl)-5-heptenoateMeSH

Chemical Formlia

C25H34F2O5 Average Molecliar Weight

452.5313 Monoisotopic Molecliar Weight

452.237430608 IUPAC Name

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 Traditional Name

tafluprost CAS Registry Number

209860-87-7 SMILES

CC(C)OC(=O)CCCC=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1C=CC(F)(F)COC1=CC=CC=C1

InChI Identifier

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

InChI Key

WSNODXPBBALQOF-VEJSHDCNSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Fatty Acyls Direct Parent

Prostaglandins and related compounds Alternative Parents

  • Phenoxy compounds
  • Phenol ethers
  • Fatty acid esters
  • Alkyl aryl ethers
  • Cyclopentanols
  • Cyclic alcohols and derivatives
  • Carboxylic acid esters
  • Monocarboxylic acids and derivatives
  • Organofluorides
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Alkyl fluorides

    • Substituents

  • Prostaglandin skeleton
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Fatty acid ester
  • Benzenoid
  • Monocyclic benzene moiety
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organooxygen compound
  • Alkyl fluoride
  • Alcohol
  • Organohalogen compound
  • Organofluoride
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • organofluorine compound (CHEBI:66899 )
  • carboxylic ester (CHEBI:66899 )
  • prostaglandins Falpha (CHEBI:66899 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antihypertensive Agents
  • Neuroprotective Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Liquid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility5.28e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0053 mg/mLALOGPS logP4.46ALOGPS logP4.29ChemAxon logS-4.9ALOGPS pKa (Strongest Acidic)14.51ChemAxon pKa (Strongest Basic)-2.9ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area75.99 Å2ChemAxon Rotatable Bond Count13ChemAxon Refractivity120.59 m3·mol-1ChemAxon Polarizability48.65 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08819

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08819

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08819 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    8044182 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Tafluprost NuGOwiki Link

    HMDB15704 Metagene Link

    HMDB15704 METLIN ID

    Not Available PubChem Compound

    9868491 PDB ID

    Not Available ChEBI ID

    66899

    Product: Carbimazole

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H: Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. [PubMed:15037111 ]
    2. Pantcheva MB, Seibold LK, Awadallah NS, Kahook MY: Tafluprost: a novel prostaglandin analog for treatment of glaucoma. Adv Ther. 2011 Sep;28(9):707-15. doi: 10.1007/s12325-011-0055-8. Epub 2011 Aug 18. [PubMed:21858491 ]
    3. Fukano Y, Kawazu K: Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats. Drug Metab Dispos. 2009 Aug;37(8):1622-34. doi: 10.1124/dmd.108.024885. Epub 2009 May 28. [PubMed:19477946 ]
    4. Papadia M, Bagnis A, Scotto R, Traverso CE: Tafluprost for glaucoma. Expert Opin Pharmacother. 2011 Oct;12(15):2393-401. doi: 10.1517/14656566.2011.606810. [PubMed:21916788 ]

    PMID: 2625135

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