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=C(O2)C=CC=C3)S(=O)(=O)C4=CC=CC=C14
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 |
|---|---|---|
| New serotonin 5-HT(1A) receptor agonists with neuroprotective effect against ischemic cell damage. | 2011-12-08 |
|
| Repinotan, a selective 5-HT1A-R-agonist, antagonizes morphine-induced ventilatory depression in anesthetized rats. | 2010-10 |
|
| A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full. | 2010-04-22 |
|
| 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). | 2009-11 |
|
| Neither in vivo MRI nor behavioural assessment indicate therapeutic efficacy for a novel 5HT(1A) agonist in rat models of ischaemic stroke. | 2009-07-16 |
|
| 5-HT1A receptor agonist-mediated protection from MPTP toxicity in mouse and macaque models of Parkinson's disease. | 2006-07 |
|
| Evaluation of interethnic differences in repinotan pharmacokinetics by using population approach. | 2006-02 |
|
| Other neuroprotective therapies on trial in acute stroke. | 2006 |
|
| 5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis. | 2005-12-05 |
|
| Pharmacokinetics of repinotan in healthy and brain injured animals. | 2005-09 |
|
| Repinotan, A 5-HT1A agonist, in the treatment of acute ischemic stroke. | 2005-04 |
|
| Neuroprotective efficacy of repinotan HCl, a 5-HT1A receptor agonist, in animal models of stroke and traumatic brain injury. | 2005-04 |
|
| The BRAINS study: safety, tolerability, and dose-finding of repinotan in acute stroke. | 2005-02 |
|
| Effect of gender and age on the pharmacokinetics of repinotan. | 2005 |
|
| Pharmacokinetics of escalating doses of intravenous repinotan in healthy male volunteers. | 2005 |
|
| A review of the neuroprotective properties of the 5-HT1A receptor agonist repinotan HCl (BAYx3702) in ischemic stroke. | 2005 |
|
| Repinotan Bayer. | 2002-06 |
|
| Repinotan (BAY x 3702): a 5HT1A agonist in traumatically brain injured patients. | 2001-12 |
|
| 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 |
|
| Characterization of the aminomethylchroman derivative BAY x 3702 as a highly potent 5-hydroxytryptamine1A receptor agonist. | 1998-03 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:32:04 GMT 2025
by
admin
on
Mon Mar 31 18:32:04 GMT 2025
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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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Preferred Name | English | ||
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Official Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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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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DTXSID80162857
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SUB04217MIG
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DB06506
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