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 |
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Characterization of the aminomethylchroman derivative BAY x 3702 as a highly potent 5-hydroxytryptamine1A receptor agonist. | 1998 Mar |
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The selective 5-HT(1A) receptor agonist repinotan HCl attenuates histopathology and spatial learning deficits following traumatic brain injury in rats. | 2001 |
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Effect of gender and age on the pharmacokinetics of repinotan. | 2005 |
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Pharmacokinetics of escalating doses of intravenous repinotan in healthy male volunteers. | 2005 |
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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 |
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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 |
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Repinotan, a selective 5-HT1A-R-agonist, antagonizes morphine-induced ventilatory depression in anesthetized rats. | 2010 Oct |
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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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Record Version |
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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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198757
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144980-29-0
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m9527
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CHEMBL1614652
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7600
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DTXSID80162857
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SUB04217MIG
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100000085269
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DB06506
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