TARAFENACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20F4N2O2
Molecular Weight	408.3893
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC(=CC=C1)N(CC2=CC(F)=C(F)C(F)=C2)C(=O)O[C@H]3CN4CCC3CC4

InChI

InChIKey=UXZDMXYRRQJIBJ-IBGZPJMESA-N

InChI=1S/C21H20F4N2O2/c22-15-2-1-3-16(10-15)27(11-13-8-17(23)20(25)18(24)9-13)21(28)29-19-12-26-6-4-14(19)5-7-26/h1-3,8-10,14,19H,4-7,11-12H2/t19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H20F4N2O2
Molecular Weight	408.3893
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19222482 | https://clinicaltrials.gov/ct2/show/NCT01458197 | https://www.ncbi.nlm.nih.gov/pubmed/25363415 | https://adisinsight.springer.com/drugs/800024423

Tarafenacin (also known as SVT-40776) was developed as muscarinic M3 receptor antagonist for the treatment of overactive bladder. The drug participated in phase II clinical trial in patients suffering from overactive bladder, where both dose levels of tarafenacin were well tolerated. However, information about the further development of tarafenacin is not available.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21524581	Antagonist 2778		1.5 nM [IC50]

PubMed

Title	Date	PubMed
Microscopic binding of M5 muscarinic acetylcholine receptor with antagonists by homology modeling, molecular docking, and molecular dynamics simulation.	2012 Jan 12	22185605
Phase II drugs that target cholinergic receptors for the treatment of overactive bladder.	2014 Oct	24899225
The efficacy and tolerability of tarafenacin, a new muscarinic acetylcholine receptor M3 antagonist in patients with overactive bladder; randomised, double-blind, placebo-controlled phase 2 study.	2015 Feb	25363415
Current and future pharmacotherapy for treating overactive bladder.	2016 Jul	27253972

Patents

Sample Use Guides

In Vivo Use Guide

Tarafenacin 0.2 mg and Tarafenacin 0.4 mg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:48:29 UTC 2023` Edited by `admin` on `Sat Dec 16 15:48:29 UTC 2023`
Record UNII	LDV98UN52Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TARAFENACIN

Official Name

English

tarafenacin [INN]

Common Name

English

(3R)-1-AZABICYCLO(2.2.2)OCTAN-3-YL (3-FLUOROPHENYL)((3,4,5-TRIFLUOROPHENYL)METHYL)CARBAMATE

Systematic Name

English

Tarafenacin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704