Tafluprost (CED0008683)

Record Information
Version1.0
Creation Date2016-05-25 18:30:32 UTC
Update Date2026-08-22 05:25:31 UTC
Accession NumberCHEM022379
Identification
Common NameTafluprost
ClassSmall Molecule
Description
Tafluprost is an organic compound with the formula C25H34F2O5 and an average molecular weight of 452.53 g/mol. Tafluprost belongs to the eicosanoids, a subclass of fatty acyls within the organic compounds. In an industrial capacity, the substance is used as a softener and conditioner. The compound is found in healthcare, pharmaceuticals, and veterinary products, specifically within miotics and antiglaucoma preparations, where the recorded exposure route is ophthalmic. Regarding its biological activity, tafluprost acts as an agonist of the prostaglandin F2-alpha receptor (PTGFR).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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-heptenoateHMDB
Chemical FormulaC25H34F2O5
Average Molecular Mass452.531 g/mol
Monoisotopic Mass452.237 g/mol
CAS Registry Number209860-87-7
IUPAC Namepropan-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 Nametafluprost
SMILESCC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1
InChI IdentifierInChI=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 KeyWSNODXPBBALQOF-VEJSHDCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity120.59 m³·mol⁻¹ChemAxon
Polarizability48.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-052f-4439700000-5f902e96f572f76cc593Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001l-7200690000-8373b0788e1ed396a7faNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kv-3015900000-c886925c3b2c359329fbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-6119200000-4d3efe181e45c7a457c4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-9011000000-010b663ce499bf30d948Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000200000-0e451520fe294c5b8f6bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-36b6f74a5c34571e3a78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-921114351b038266dd2eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0py3-0019500000-5b4599f3f7676f5d531eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00mo-2119200000-d5684e822eb13b29e9b9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0561-9610000000-eb4fe1a3cbe0fdfe9daaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000400000-706df0cdfeceb3c1bf1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-f096008f6b882e68cef4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-08485aaf085c13d5129aNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
260.0Log mg/kg[150:460]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
398Antiglaucoma preparations and mioticsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
2 pathways
Tafluprost Drug Metabolism Action Pathway
Tafluprost Drug Metabolism Action Pathway
Tafluprost Action Pathway
Tafluprost Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureProstaglandin F2-alpha receptorP37289Bos taurusPredicted (SEA)0.467095
Solute carrier organic anion transporter family member 2A1 structureClick to view 3D structureSolute carrier organic anion transporter family member 2A1Q92959HumansPredicted (SEA)0.389246
Prostaglandin F2-alpha receptor structureClick to view 3D structureProstaglandin F2-alpha receptorP43088HumansPredicted (SEA)5.68299
Thromboxane A2 receptor structureClick to view 3D structureThromboxane A2 receptorP21731HumansPredicted (SEA)9.41976
Click to view 3D structureSolute carrier organic anion transporter family member 2A1Q9EPT5Mus musculusPredicted (SEA)1.08989
Click to view 3D structureProstaglandin F2-alpha receptorP43117Mus musculusPredicted (SEA)1.16774
Prostaglandin E2 receptor EP2 subtype structureClick to view 3D structureProstaglandin E2 receptor EP2 subtypeP43116HumansPredicted (SEA)11.8331
Prostaglandin E2 receptor EP3 subtype structureClick to view 3D structureProstaglandin E2 receptor EP3 subtypeP43115HumansPredicted (SEA)16.1926
Prostaglandin E2 receptor EP4 subtype structureClick to view 3D structureProstaglandin E2 receptor EP4 subtypeP35408HumansPredicted (SEA)16.6597
Prostacyclin receptor structureClick to view 3D structureProstacyclin receptorP43119HumansPredicted (SEA)8.32987
Click to view 3D structureProstaglandin D2 receptorQ13258HumansPredicted (SEA)13.6236
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP34995HumansPredicted (SEA)19.0731
Click to view 3D structureSolute carrier organic anion transporter family member 2B1Q9JHI3Rattus norvegicusPredicted (SEA)1.86838
Click to view 3D structureProstaglandin E2 receptor EP3 subtypeP30557Mus musculusPredicted (SEA)34.7986
Click to view 3D structureProstaglandin E2 receptor EP4 subtypeP32240Mus musculusPredicted (SEA)36.8227
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP35375Mus musculusPredicted (SEA)28.7264
Click to view 3D structureProstaglandin E2 receptor EP2 subtypeQ62053Mus musculusPredicted (SEA)23.5883
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)1053.3
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)1170.07
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)971.87
Prostacyclin synthase structureClick to view 3D structureProstacyclin synthaseQ16647HumansPredicted (SEA)7.70707
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)870.432
Click to view 3D structureEsteraseA3QR02Chilo suppressalisPredicted (SEA)9.10836
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)467.796
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)1892.2
Concentrations
Not Available
External Links
DrugBank IDDB08819
HMDB IDHMDB0015704
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTafluprost
Chemspider ID8044182
ChEBI ID66899
PubChem Compound ID9868491
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21423041
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21491995
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22049909
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22107041
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22275814
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22310086
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22399693
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22499235
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22583577
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22606063
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22654492
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22669351
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22690824
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22695966
15. 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.
16. 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.
17. 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.
18. 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.
19. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
20. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
21. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
22. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
23. The lipid handbook with CD-ROM