TAPRENEPAG ISOPROPYL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H28N4O5S
Molecular Weight	520.6
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC(=O)COC1=CC(CN(CC2=CC=C(C=C2)N3C=CC=N3)S(=O)(=O)C4=CN=CC=C4)=CC=C1

InChI

InChIKey=NVPXUFQLKWKBHK-UHFFFAOYSA-N

InChI=1S/C27H28N4O5S/c1-21(2)36-27(32)20-35-25-7-3-6-23(16-25)19-30(37(33,34)26-8-4-13-28-17-26)18-22-9-11-24(12-10-22)31-15-5-14-29-31/h3-17,21H,18-20H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24720348 | https://www.ncbi.nlm.nih.gov/pubmed/21376717 | https://www.pfizer.com/sites/default/files/product-pipeline/pipeline_2011_0811.pdf

Taprenepag isopropyl (also known as PF-04217329) a prodrug of CP-544326 (active acid metabolite), a potent and selective EP(2) receptor agonist. Taprenepag isopropyl was studied in a clinical trials phase II involving patients with primary open angle glaucoma. According to Pfizer’s pipelines in May 2011, the study was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin E2 receptor EP2 subtype 5 Target ID: P43116 Gene ID: 5732.0 Gene Symbol: PTGER2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21376717 \| https://www.ncbi.nlm.nih.gov/pubmed/21851167	Agonist 2678		2.8 nM [EC50]

PubMed

Title	Date	PubMed
Effect of PF-04217329 a prodrug of a selective prostaglandin EP(2) agonist on intraocular pressure in preclinical models of glaucoma.	2011 Sep	21376717
A phase 2, randomized, dose-response trial of taprenepag isopropyl (PF-04217329) versus latanoprost 0.005% in open-angle glaucoma and ocular hypertension.	2011 Sep	21851167
Prostaglandin analogues and nitric oxide contribution in the treatment of ocular hypertension and glaucoma.	2019 Apr	29669171

Patents

Sample Use Guides

In Vivo Use Guide

Stage I: 3 cohorts (total n = 67) received 1 drop of taprenepag isopropyl unit dose formulation qPM/eye for 14 days: low dose: 0.0025%, 0.005%, vehicle; middle dose: 0.01%, 0.015%, vehicle; high dose: 0.02%, 0.03%, vehicle. Stage II: 7 groups (total n = 250) received 1 drop of taprenepag isopropyl multidose formulation qPM/eye for 28 days: 0.005%, 0.01%, 0.015% monotherapy; each in unfixed combination with latanoprost 0.005%, or latanoprost monotherapy.

Route of Administration: Other

Name

Type

Language

TAPRENEPAG ISOPROPYL

Official Name

English

TAPRENEPAG ISOPROPYL [USAN]

Common Name

English

Taprenepag isopropyl [WHO-DD]

Common Name

English

1-Methylethyl 2-(3-{[{[4-(1H-pyrazol-1-yl)phenyl]methyl}(pyridin-3-ylsulfonyl)amino]methyl}phenoxy)acetate

Systematic Name

English

ACETIC ACID, 2-(3-((((4-(1H-PYRAZOL-1-YL)PHENYL)METHYL)(3-PYRIDINYLSULFONYL)AMINO)METHYL)PHENOXY)-,1-METHYLETHYL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568