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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24N2O4S
Molecular Weight 400.491
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REPINOTAN

SMILES

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

InChI

InChIKey=YGYBFMRFXNDIPO-QGZVFWFLSA-N
InChI=1S/C21H24N2O4S/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/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

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

PubMed

TitleDatePubMed
Characterization of the aminomethylchroman derivative BAY x 3702 as a highly potent 5-hydroxytryptamine1A receptor agonist.
1998 Mar
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
The selective 5-HT(1A) receptor agonist repinotan HCl attenuates histopathology and spatial learning deficits following traumatic brain injury in rats.
2001
Repinotan (BAY x 3702): a 5HT1A agonist in traumatically brain injured patients.
2001 Dec
Repinotan Bayer.
2002 Jun
Repinotan, A 5-HT1A agonist, in the treatment of acute ischemic stroke.
2005 Apr
Neuroprotective efficacy of repinotan HCl, a 5-HT1A receptor agonist, in animal models of stroke and traumatic brain injury.
2005 Apr
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.
2005 Dec 5
The BRAINS study: safety, tolerability, and dose-finding of repinotan in acute stroke.
2005 Feb
Evaluation of interethnic differences in repinotan pharmacokinetics by using population approach.
2006 Feb
5-HT1A receptor agonist-mediated protection from MPTP toxicity in mouse and macaque models of Parkinson's disease.
2006 Jul
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
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
Repinotan, a selective 5-HT1A-R-agonist, antagonizes morphine-induced ventilatory depression in anesthetized rats.
2010 Oct
New serotonin 5-HT(1A) receptor agonists with neuroprotective effect against ischemic cell damage.
2011 Dec 8
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:35:20 UTC 2023
Edited
by admin
on Fri Dec 15 16:35:20 UTC 2023
Record UNII
05PB82Z52L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REPINOTAN
INN   MI   WHO-DD  
INN  
Official Name English
REPINOTAN [MI]
Common Name English
Repinotan [WHO-DD]
Common Name English
repinotan [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
Code System Code Type Description
FDA UNII
05PB82Z52L
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
WIKIPEDIA
REPINOTAN
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
NCI_THESAURUS
C74388
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
PUBCHEM
198757
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
CAS
144980-29-0
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
MERCK INDEX
m9527
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1614652
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
INN
7600
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID80162857
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
EVMPD
SUB04217MIG
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
SMS_ID
100000085269
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
DRUG BANK
DB06506
Created by admin on Fri Dec 15 16:35:20 UTC 2023 , Edited by admin on Fri Dec 15 16:35:20 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY