Identification

Name
Tafluprost
Accession Number
DB08819
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • AFP-168
External IDs
MK-2452
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SaflutanSolution4.5 mcgOphthalmicPurdue PharmaNot applicableNot applicableCanada
ZioptanSolution.0045 mg/.3mLOphthalmicMerck Sharp & Dohme Limited2012-02-102017-03-09Us
ZioptanSolution / drops.0045 mg/.3mLOphthalmicAkorn2014-11-26Not applicableUs
International/Other Brands
Taflotan (Regeneron Pharmaceuticals) / Zioptan
Categories
UNII
1O6WQ6T7G3
CAS number
209860-87-7
Weight
Average: 452.5313
Monoisotopic: 452.237430608
Chemical Formula
C25H34F2O5
InChI Key
WSNODXPBBALQOF-VEJSHDCNSA-N
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
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
SMILES
CC(C)OC(=O)CCC\C=C/C[[email protected]]1[[email protected]@H](O)C[[email protected]@H](O)[[email protected]@H]1\C=C\C(F)(F)COC1=CC=CC=C1

Pharmacology

Indication

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

Structured Indications
Pharmacodynamics

Tafluprost is a novel prostaglandin analog with a high affinity for the fluoroprostaglandin (FP) receptor PGF2α. 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.

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.

TargetActionsOrganism
AProstaglandin F2-alpha receptor
agonist
Human
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 pgmin/mL - 432 pgmin/mL.

Volume of distribution

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

Protein binding
Not Available
Metabolism

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 β-oxidation and phase II conjugation into 1,2,3,4-tetranor acid.

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.

Half life
Not Available
Clearance
Not Available
Toxicity

Most common ocular adverse reaction is conjunctival hyperemia (range 4% – 20%).

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
(4R)-limoneneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Limonene, (+)-.Investigational
AceclofenacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Aceclofenac.Approved, Investigational
AcemetacinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
Acetylsalicylic acidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Acetylsalicylic acid.Approved, Vet Approved
AdapaleneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Adapalene.Approved
AlclofenacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Alclofenac.Approved, Withdrawn
AlminoprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Alminoprofen.Experimental
AndrographolideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Andrographolide.Investigational
AnisodamineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Anisodamine.Investigational
AntipyrineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Antipyrine.Approved
ApocyninThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Apocynin.Investigational
ApremilastThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Apremilast.Approved, Investigational
AzapropazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Azapropazone.Withdrawn
AzelastineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Azelastine.Approved
BalsalazideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Balsalazide.Approved, Investigational
BendazacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Bendazac.Experimental
BenorilateThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Benorilate.Experimental
BenoxaprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Benoxaprofen.Withdrawn
BenzydamineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Benzydamine.Approved
BevoniumThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Bevonium.Experimental
BromfenacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Bromfenac.Approved
BucillamineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Bucillamine.Investigational
BufexamacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Bufexamac.Experimental
BumadizoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Bumadizone.Experimental
Carbaspirin calciumThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Carbaspirin calcium.Experimental, Investigational
CarprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Carprofen.Approved, Vet Approved, Withdrawn
CastanospermineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Castanospermine.Experimental
CelecoxibThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Celecoxib.Approved, Investigational
ChloroquineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Chloroquine.Approved, Vet Approved
Choline magnesium trisalicylateThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Choline magnesium trisalicylate.Approved
ClonixinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Clonixin.Approved
CurcuminThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Curcumin.Investigational
DiclofenacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Diclofenac.Approved, Vet Approved
DifenpiramideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Difenpiramide.Experimental
DiflunisalThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Diflunisal.Approved
DroxicamThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Droxicam.Withdrawn
DuvelisibThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Duvelisib.Investigational
E-6201The therapeutic efficacy of Tafluprost can be decreased when used in combination with E-6201.Investigational
EpirizoleThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Epirizole.Approved
EtanerceptThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Etanercept.Approved, Investigational
EthenzamideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Ethenzamide.Experimental
EtodolacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Etofenamate.Approved, Investigational
EtoricoxibThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Etoricoxib.Approved, Investigational
Evening primrose oilThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Evening primrose oil.Approved, Investigational
ExisulindThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Exisulind.Investigational
FelbinacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Felbinac.Experimental
FenbufenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Fenbufen.Approved
FenoprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Fenoprofen.Approved
FentiazacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Fentiazac.Experimental
FeprazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Feprazone.Experimental
Ferulic acidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Ferulic acid.Experimental
FloctafenineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Floctafenine.Approved, Withdrawn
FlunixinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Flunixin.Vet Approved
FlunoxaprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Flunoxaprofen.Experimental
FlurbiprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Flurbiprofen.Approved, Investigational
GuacetisalThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Guacetisal.Experimental
HigenamineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Higenamine.Investigational
IbuprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Ibuprofen.Approved
IbuproxamThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Ibuproxam.Withdrawn
IcatibantThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Icatibant.Approved
Imidazole salicylateThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Imidazole salicylate.Experimental
IndobufenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Indobufen.Investigational
IndomethacinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Indomethacin.Approved, Investigational
IndoprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Indoprofen.Withdrawn
IsoxicamThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Isoxicam.Withdrawn
KebuzoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Kebuzone.Experimental
KetoprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Ketoprofen.Approved, Vet Approved
KetorolacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Ketorolac.Approved
LeflunomideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Leflunomide.Approved, Investigational
LisofyllineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Lisofylline.Investigational
LonazolacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Lonazolac.Experimental
LornoxicamThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Lornoxicam.Approved, Investigational
LoxoprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Loxoprofen.Approved, Investigational
LumiracoxibThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Lumiracoxib.Approved, Investigational
Magnesium salicylateThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Magnesium salicylate.Approved
MasoprocolThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Masoprocol.Approved, Investigational
Meclofenamic acidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Mefenamic acid.Approved
MeloxicamThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Meloxicam.Approved, Vet Approved
MesalazineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Mesalazine.Approved
MetamizoleThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Metamizole.Investigational, Withdrawn
MizoribineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Mizoribine.Investigational
MofebutazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Mofebutazone.Experimental
Mycophenolate mofetilThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Mycophenolic acid.Approved
NabumetoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Nabumetone.Approved
NafamostatThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Nafamostat.Approved, Investigational
NaftifineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Naftifine.Approved
NaproxenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Naproxen.Approved, Vet Approved
NepafenacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Nepafenac.Approved
NifenazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Nifenazone.Experimental
Niflumic AcidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Niflumic Acid.Approved
NimesulideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NitroaspirinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Nitroaspirin.Investigational
OlopatadineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Olopatadine.Approved
OlsalazineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Olsalazine.Approved
OrgoteinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Orgotein.Vet Approved
OxaprozinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Oxaprozin.Approved
OxyphenbutazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Oxyphenbutazone.Approved, Withdrawn
ParecoxibThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Parecoxib.Approved
ParthenolideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Parthenolide.Investigational
PhenylbutazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
PimecrolimusThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Pimecrolimus.Approved, Investigational
PirfenidoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Pirfenidone.Approved, Investigational
PiroxicamThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Piroxicam.Approved, Investigational
PirprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Pirprofen.Experimental
PranoprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Pranoprofen.Experimental, Investigational
ProglumetacinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Proglumetacin.Experimental
PropacetamolThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Propacetamol.Approved, Investigational
PropyphenazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Propyphenazone.Experimental
ProquazoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Proquazone.Experimental
PTC299The therapeutic efficacy of Tafluprost can be decreased when used in combination with PTC299.Investigational
ResveratrolThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Resveratrol.Approved, Experimental, Investigational
RofecoxibThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Rofecoxib.Investigational, Withdrawn
SalicylamideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Salicylamide.Approved
Salicylic acidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Salicylic acid.Approved, Vet Approved
SalsalateThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Salsalate.Approved
SemapimodThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Semapimod.Investigational
SeratrodastThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Seratrodast.Approved
SerrapeptaseThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Serrapeptase.Investigational
SRT501The therapeutic efficacy of Tafluprost can be decreased when used in combination with SRT501.Investigational
SulfasalazineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Sulindac.Approved
SuprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Suprofen.Approved, Withdrawn
SuxibuzoneThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Suxibuzone.Experimental
TarenflurbilThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tarenflurbil.Investigational
TenidapThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tenidap.Experimental
TenoxicamThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tenoxicam.Approved
TepoxalinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tepoxalin.Vet Approved
TeriflunomideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Teriflunomide.Approved
Tiaprofenic acidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tiaprofenic acid.Approved
TinoridineThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tinoridine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tolfenamic Acid.Approved
TolmetinThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tolmetin.Approved
TranilastThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tranilast.Approved, Investigational
TribenosideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Tribenoside.Experimental
TriptolideThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Triptolide.Investigational
ValdecoxibThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Valdecoxib.Investigational, Withdrawn
ZaltoprofenThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Zaltoprofen.Approved, Investigational
ZileutonThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Zileuton.Approved, Investigational, Withdrawn
ZomepiracThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Zomepirac.Withdrawn
Food Interactions
Not Available

References

General References
  1. 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]
  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. 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]
  4. 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]
External Links
Human Metabolome Database
HMDB15704
KEGG Drug
D06274
PubChem Compound
9868491
PubChem Substance
175427102
ChemSpider
8044182
ChEBI
66899
ChEMBL
CHEMBL1963683
PharmGKB
PA165958432
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tafluprost
ATC Codes
S01EE05 — Tafluprost
AHFS Codes
  • 52:40.28 — Prostaglandin Analogs
FDA label
Download (274 KB)
MSDS
Download (22.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentGlaucoma / Ocular Hypertension1
1, 2CompletedTreatmentGlaucoma and Ocular Hypertension1
3CompletedTreatmentGlaucoma / Ocular Hypertension1
3CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)6
3Unknown StatusTreatmentGlaucoma1
4CompletedTreatmentGlaucoma1
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG)1
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension2
4CompletedTreatmentGlaucoma / Ocular Hypertension1
4CompletedTreatmentGlaucoma / Ocular Surface Disease1
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)2
4RecruitingTreatmentGlaucoma / Ocular Hypertension1
4Unknown StatusPreventionGlaucoma / Ocular Hypertension / Thyroid Eye Disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionOphthalmic4.5 mcg
SolutionOphthalmic.0045 mg/.3mL
Solution / dropsOphthalmic.0045 mg/.3mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5886035No1997-12-182017-12-18Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)87.5 °CNot Available
boiling point (°C)100°C Not Available
water solubilityInsoluble FDA label
logP4.05Not Available
pKa5.5-6.7FDA label
Predicted Properties
PropertyValueSource
Water Solubility0.00528 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9644
Blood Brain Barrier+0.8687
Caco-2 permeable+0.5372
P-glycoprotein substrateSubstrate0.5871
P-glycoprotein inhibitor INon-inhibitor0.9015
P-glycoprotein inhibitor IINon-inhibitor0.7888
Renal organic cation transporterNon-inhibitor0.8711
CYP450 2C9 substrateNon-substrate0.8086
CYP450 2D6 substrateNon-substrate0.854
CYP450 3A4 substrateSubstrate0.6508
CYP450 1A2 substrateNon-inhibitor0.75
CYP450 2C9 inhibitorNon-inhibitor0.7344
CYP450 2D6 inhibitorNon-inhibitor0.9056
CYP450 2C19 inhibitorNon-inhibitor0.6873
CYP450 3A4 inhibitorNon-inhibitor0.8038
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7418
Ames testNon AMES toxic0.7286
CarcinogenicityNon-carcinogens0.9028
BiodegradationNot ready biodegradable0.9737
Rat acute toxicity3.7129 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9787
hERG inhibition (predictor II)Non-inhibitor0.7362
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
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
show 3 more
Substituents
Prostaglandin skeleton / Phenoxy compound / Phenol ether / Alkyl aryl ether / Fatty acid ester / Benzenoid / Monocyclic benzene moiety / Cyclopentanol / Cyclic alcohol / Secondary alcohol
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organofluorine compound, carboxylic ester, prostaglandins Falpha (CHEBI:66899)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin f receptor activity
Specific Function
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis...
Gene Name
PTGFR
Uniprot ID
P43088
Uniprot Name
Prostaglandin F2-alpha receptor
Molecular Weight
40054.1 Da
References
  1. 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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Roh YJ, Park YG, Kang S, Kim SY, Moon JI: Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch Clin Exp Ophthalmol. 2012 Dec;250(12):1765-75. doi: 10.1007/s00417-012-2125-2. Epub 2012 Aug 22. [PubMed:22910791]

Drug created on February 24, 2012 10:29 / Updated on January 14, 2018 10:04