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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
Structure of PIROMELATINE

SMILES

COC1=CC=C2NC=C(CCNC(=O)C3=CC(=O)C=CO3)C2=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)

HIDE SMILES / InChI

Molecular Formula C17H16N2O4
Molecular Weight 312.3199
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
NEU-P11, a novel melatonin agonist, inhibits weight gain and improves insulin sensitivity in high-fat/high-sucrose-fed rats.
2009 Apr
Antidepressant- and anxiolytic effects of the novel melatonin agonist Neu-P11 in rodent models.
2010 Jul
Investigational melatonin receptor agonists.
2010 Jun
Cardiovascular effects of melatonin receptor agonists.
2012 Nov
Determination of the novel melatonin agonist Neu-P11 in plasma samples by liquid chromatography-tandem mass spectrometry.
2013 Feb 23
A novel melatonin agonist Neu-P11 facilitates memory performance and improves cognitive impairment in a rat model of Alzheimer' disease.
2013 Jun
Blood pressure reducing effects of piromelatine and melatonin in spontaneously hypertensive rats.
2013 Sep
Antinociceptive effects of novel melatonin receptor agonists in mouse models of abdominal pain.
2014 Feb 7
Piromelatine, a novel melatonin receptor agonist, stabilizes metabolic profiles and ameliorates insulin resistance in chronic sleep restricted rats.
2014 Mar 15
Exploration on mechanism of a new type of melatonin receptor agonist Neu-p11 in hypoxia-reoxygenation injury of myocardial cells.
2014 Nov
Piromelatine exerts antinociceptive effect via melatonin, opioid, and 5HT1A receptors and hypnotic effect via melatonin receptors in a mouse model of neuropathic pain.
2014 Oct
Role of Neu-p11/luzindole in the regulation of insulin signaling pathways and insulin resistance.
2016 May
Melatonin, but not melatonin receptor agonists Neu-P11 and Neu-P67, attenuates TNBS-induced colitis in mice.
2016 May
Inflammaging, Metabolic Syndrome and Melatonin: A Call for Treatment Studies.
2017
Neu-P11, a novel MT1/MT2 agonist, reverses diabetes by suppressing the hypothalamic-pituitary-adrenal axis in rats.
2017 Oct 5
Circadian Rhythm and Melatonin in the Treatment of Depression.
2018
Melatonin Receptor Agonist Piromelatine Ameliorates Impaired Glucose Metabolism in Chronically Stressed Rats Fed a High-Fat Diet.
2018 Jan
Insomnia in Elderly Patients: Recommendations for Pharmacological Management.
2018 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:21:56 UTC 2023
Edited
by admin
on Sat Dec 16 01:21:56 UTC 2023
Record UNII
S3UN2146K9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIROMELATINE
INN   WHO-DD  
INN  
Official Name English
4H-PYRAN-2-CARBOXAMIDE, N-(2-(5-METHOXY-1H-INDOL-3-YL)ETHYL)-4-OXO-
Systematic Name English
NEU-P-11
Code English
piromelatine [INN]
Common Name English
N-(2-(5-METHOXY-1H-INDOL-3-YL)ETHYL)-4-OXO-4H-PYRAN-2-CARBOXAMIDE
Systematic Name English
Piromelatine [WHO-DD]
Common Name English
NEU-P11
Code English
Code System Code Type Description
SMS_ID
300000034334
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
NCI_THESAURUS
C170326
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
PUBCHEM
24815904
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID90241566
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
INN
9657
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
CAS
946846-83-9
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
DRUG BANK
DB12288
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
FDA UNII
S3UN2146K9
Created by admin on Sat Dec 16 01:21:56 UTC 2023 , Edited by admin on Sat Dec 16 01:21:56 UTC 2023
PRIMARY
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TARGET -> AGONIST
TARGET -> AGONIST
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TARGET -> AGONIST
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ACTIVE MOIETY