U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H34F2O5
Molecular Weight 452.5313
Optical Activity ( + )
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of Tafluprost

SMILES

CC(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)COC2=CC=CC=C2

InChI

InChIKey=WSNODXPBBALQOF-VEJSHDCNSA-N
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

HIDE SMILES / InChI

Description

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. A prostaglandin analogue ester prodrug used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Tafluprost was approved for use in the U.S. on February 10, 2012. Tafluprost, preserved and preservative-free formulations, received marketing approval for the reduction of elevated intraocular pressure (IOP) in open-angle glaucoma and ocular hypertension in several European and Nordic countries as well as Japan, and some other Asia Pacific markets.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.5 nM [IC50]
0.4 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
ZIOPTAN
Secondary
ZIOPTAN

Cmax

ValueDoseCo-administeredAnalytePopulation
24.4 pg/mL
1 drop single, topical
TAFLUPROST ACID plasma
Homo sapiens
26 pg/mL
1 drop single, topical
TAFLUPROST ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
405.9 pg × min/mL
1 drop single, topical
TAFLUPROST ACID plasma
Homo sapiens
394 pg × min/mL
1 drop single, topical
TAFLUPROST ACID plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
The affinity for the FP receptor shown by AFP-172 (Ki : 0.4 nm) was 12 times that of PhXA85 ( Ki : 4.7 nm), a carboxylic acid of latanoprost. For the prostanoid FP receptor-binding study, it was used a clonal cell line that stably expresses the recombinant human prostanoid FP receptor. The AFP-172 showed a high affinity for the human prostanoid FP receptor, with an EC50 of 0,53 nM.