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

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
Characterization of the aminomethylchroman derivative BAY x 3702 as a highly potent 5-hydroxytryptamine1A receptor agonist.	1998 Mar	9495870
Oral post-lesion administration of 5-HT(1A) receptor agonist repinotan hydrochloride (BAY x 3702) attenuates NMDA-induced delayed neuronal death in rat magnocellular nucleus basalis.	2001	11738499
The selective 5-HT(1A) receptor agonist repinotan HCl attenuates histopathology and spatial learning deficits following traumatic brain injury in rats.	2001	11591455
Repinotan (BAY x 3702): a 5HT1A agonist in traumatically brain injured patients.	2001 Dec	11780862
Repinotan Bayer.	2002 Jun	12137415
Effect of gender and age on the pharmacokinetics of repinotan.	2005	17523762
Pharmacokinetics of escalating doses of intravenous repinotan in healthy male volunteers.	2005	17523761
Repinotan, A 5-HT1A agonist, in the treatment of acute ischemic stroke.	2005 Apr	15857296
Neuroprotective efficacy of repinotan HCl, a 5-HT1A receptor agonist, in animal models of stroke and traumatic brain injury.	2005 Apr	15674237
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.	2005 Dec 5	16310183
The BRAINS study: safety, tolerability, and dose-finding of repinotan in acute stroke.	2005 Feb	15825548
Pharmacokinetics of repinotan in healthy and brain injured animals.	2005 Sep	15966026
A review of the neuroprotective properties of the 5-HT1A receptor agonist repinotan HCl (BAYx3702) in ischemic stroke.	2005 Winter	16614737
Other neuroprotective therapies on trial in acute stroke.	2006	16651823
Evaluation of interethnic differences in repinotan pharmacokinetics by using population approach.	2006 Feb	16547395
5-HT1A receptor agonist-mediated protection from MPTP toxicity in mouse and macaque models of Parkinson's disease.	2006 Jul	16545572
Neither in vivo MRI nor behavioural assessment indicate therapeutic efficacy for a novel 5HT(1A) agonist in rat models of ischaemic stroke.	2009 Jul 16	19607699
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

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