REPINOTAN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24N2O4S.ClH
Molecular Weight	436.952
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.O=C1N(CCCCNC[C@H]2CCC3=CC=CC=C3O2)S(=O)(=O)C4=C1C=CC=C4

InChI

InChIKey=IGKYREHZJIHPML-UNTBIKODSA-N

InChI=1S/C21H24N2O4S.ClH/c24-21-18-8-2-4-10-20(18)28(25,26)23(21)14-6-5-13-22-15-17-12-11-16-7-1-3-9-19(16)27-17;/h1-4,7-10,17,22H,5-6,11-15H2;1H/t17-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C21H24N2O4S
Molecular Weight	400.491
Charge	0
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB06506 | https://www.ncbi.nlm.nih.gov/pubmed/15674237 | https://www.sciencedirect.com/science/article/abs/pii/S0306452201004444 | https://clinicaltrials.gov/ct2/show/NCT00044915

Repinotan (BAYX3702) is a highly selective 5-HT1A receptor agonist that has shown neuroprotective effects in animals (attenuating NMDA-induced delayed neuronal death in rats). Repinotan inhibits glutamate induced depolarization. A variety of mechanisms and pathways is thought to be involved in its efficacy, such as activation of the anti-apoptotic phosphatidylinositol 3-kinase (PI-3K) pathway, inhibition of glutamate release, extracellular-regulated kinase (Erk)-stimulated Bcl-2 expression or inhibition of caspase-3 activity, and increased release of the neurite extension factor S-100 beta. Based on results in animal studies, repinotan could be a promising candidate for treating acute ischemic stroke in humans. A phase II clinical trials in patients with acute ischemic stroke was completed in 2009.

Approval Year

PubMed

Title	Date	PubMed
Effect of gender and age on the pharmacokinetics of repinotan.	2005	17523762
The BRAINS study: safety, tolerability, and dose-finding of repinotan in acute stroke.	2005 Feb	15825548
A review of the neuroprotective properties of the 5-HT1A receptor agonist repinotan HCl (BAYx3702) in ischemic stroke.	2005 Winter	16614737
A randomized, double-blind, placebo-controlled trial to evaluate the efficacy, safety, tolerability, and pharmacokinetic/pharmacodynamic effects of a targeted exposure of intravenous repinotan in patients with acute ischemic stroke: modified Randomized Exposure Controlled Trial (mRECT).	2009 Nov	19745176
A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full.	2010 Apr 22	20412562
Repinotan, a selective 5-HT1A-R-agonist, antagonizes morphine-induced ventilatory depression in anesthetized rats.	2010 Oct	20802053
New serotonin 5-HT(1A) receptor agonists with neuroprotective effect against ischemic cell damage.	2011 Dec 8	22029386

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:58:37 UTC 2023` Edited by `admin` on `Fri Dec 15 15:58:37 UTC 2023`
Record UNII	1KBQ63168A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

REPINOTAN HYDROCHLORIDE

Common Name

English

BAY X 3702

Code

English

REPINOTAN HYDROCHLORIDE [MI]

Common Name

English

Code System Code Type Description

FDA UNII

1KBQ63168A