Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H16N2O4 |
| Molecular Weight | 312.3199 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(NC=C2CCNC(=O)C3=CC(=O)C=CO3)C=C1
InChI
InChIKey=PNTNBIHOAPJYDB-UHFFFAOYSA-N
InChI=1S/C17H16N2O4/c1-22-13-2-3-15-14(9-13)11(10-19-15)4-6-18-17(21)16-8-12(20)5-7-23-16/h2-3,5,7-10,19H,4,6H2,1H3,(H,18,21)
Piromelatine is an investigational therapy being developed by Neurim Pharmaceuticals to manage sleeping difficulties. The compound is now being studied for its potential to improve cognitive function and slow the progression of Alzheimer’s disease by promoting better sleep. It acts primarily as an agonist of MT1/MT2/MT3 melatonin receptors and serotonin 5-HT1A and 5-HT1D receptors, but reportedly also is a low-affinity antagonist of 5-HT2B, P2X3, and TRPV1 receptors. Piromelatine may benefit control of circadian rhythm, metabolism, cognition and mood. Preclinical studies have reported cognitive improvement in rats that received hippocampal Aβ42 injections to simulate Alzheimer’s disease. There are also reports on painkilling and hypnotic effects in a mouse model of neuropathic pain, as well as blood pressure lowering in rats. Piromelatine is in phase II clinical trial for the treatment of Alzheimer's disease, Insomnia, Ocular hypertension and Open-angle glaucoma.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Insomnia in Elderly Patients: Recommendations for Pharmacological Management. | 2018-09 |
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| Melatonin Receptor Agonist Piromelatine Ameliorates Impaired Glucose Metabolism in Chronically Stressed Rats Fed a High-Fat Diet. | 2018-01 |
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| Circadian Rhythm and Melatonin in the Treatment of Depression. | 2018 |
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| Neu-P11, a novel MT1/MT2 agonist, reverses diabetes by suppressing the hypothalamic-pituitary-adrenal axis in rats. | 2017-10-05 |
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| Inflammaging, Metabolic Syndrome and Melatonin: A Call for Treatment Studies. | 2017 |
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| Anticonvulsant activity of melatonin, but not melatonin receptor agonists Neu-P11 and Neu-P67, in mice. | 2016-07-01 |
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| Piromelatine ameliorates memory deficits associated with chronic mild stress-induced anhedonia in rats. | 2016-06 |
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| Role of Neu-p11/luzindole in the regulation of insulin signaling pathways and insulin resistance. | 2016-05 |
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| Melatonin, but not melatonin receptor agonists Neu-P11 and Neu-P67, attenuates TNBS-induced colitis in mice. | 2016-05 |
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| Melatonin and Synthetic Melatoninergic Agonists in Psychiatric and Age-associated Disorders: Successful and Unsuccessful Approaches. | 2016 |
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| Neuroprotective mechanism of the novel melatonin derivative Neu-P11 in brain ischemia related models. | 2015-12 |
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| Current Phase II investigational therapies for insomnia. | 2015-03 |
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| Exploration on mechanism of a new type of melatonin receptor agonist Neu-p11 in hypoxia-reoxygenation injury of myocardial cells. | 2014-11 |
|
| Piromelatine exerts antinociceptive effect via melatonin, opioid, and 5HT1A receptors and hypnotic effect via melatonin receptors in a mouse model of neuropathic pain. | 2014-10 |
|
| Piromelatine, a novel melatonin receptor agonist, stabilizes metabolic profiles and ameliorates insulin resistance in chronic sleep restricted rats. | 2014-03-15 |
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| Antinociceptive effects of novel melatonin receptor agonists in mouse models of abdominal pain. | 2014-02-07 |
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| Blood pressure reducing effects of piromelatine and melatonin in spontaneously hypertensive rats. | 2013-09 |
|
| Neu-p11 reduces clock/apelin expression in insulin-resistant mouse adipocyte model. | 2013-09 |
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| Piromelatine decreases triglyceride accumulation in insulin resistant 3T3-L1 adipocytes: role of ATGL and HSL. | 2013-08 |
|
| A novel melatonin agonist Neu-P11 facilitates memory performance and improves cognitive impairment in a rat model of Alzheimer' disease. | 2013-06 |
|
| Determination of the novel melatonin agonist Neu-P11 in plasma samples by liquid chromatography-tandem mass spectrometry. | 2013-02-23 |
|
| Elucidation of Neu-P11 metabolism in urine of volunteers by liquid chromatography-tandem mass spectrometry. | 2013-02-22 |
|
| Cardiovascular effects of melatonin receptor agonists. | 2012-11 |
|
| Antidepressant- and anxiolytic effects of the novel melatonin agonist Neu-P11 in rodent models. | 2010-07 |
|
| Investigational melatonin receptor agonists. | 2010-06 |
|
| NEU-P11, a novel melatonin agonist, inhibits weight gain and improves insulin sensitivity in high-fat/high-sucrose-fed rats. | 2009-04 |
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ACTIVE MOIETY
