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
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
| 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
| Title | Date | PubMed |
|---|---|---|
| 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 |
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| Neuroprotective efficacy of repinotan HCl, a 5-HT1A receptor agonist, in animal models of stroke and traumatic brain injury. | 2005 Apr |
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| 5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis. | 2005 Dec 5 |
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| The BRAINS study: safety, tolerability, and dose-finding of repinotan in acute stroke. | 2005 Feb |
|
| Pharmacokinetics of repinotan in healthy and brain injured animals. | 2005 Sep |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:35:20 GMT 2023
by
admin
on
Fri Dec 15 16:35:20 GMT 2023
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| Record UNII |
05PB82Z52L
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C47794
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05PB82Z52L
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REPINOTAN
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C74388
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m9527
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DB06506
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