PIROMELATINE

Investigational

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 Search

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)

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

Description
Sources: https://adisinsight.springer.com/drugs/800032086 | https://alzheimersnewstoday.com/piromelatine/ | https://www.alzforum.org/therapeutics/piromelatine

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
Antidepressant- and anxiolytic effects of the novel melatonin agonist Neu-P11 in rodent models.	2010 Jul	20581849
Cardiovascular effects of melatonin receptor agonists.	2012 Nov	22916799
Determination of the novel melatonin agonist Neu-P11 in plasma samples by liquid chromatography-tandem mass spectrometry.	2013 Feb 23	23245235
Circadian Rhythm and Melatonin in the Treatment of Depression.	2018	30073921
Insomnia in Elderly Patients: Recommendations for Pharmacological Management.	2018 Sep	30058034

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:48:41 GMT 2025` Edited by `admin` on `Mon Mar 31 20:48:41 GMT 2025`
Record UNII	S3UN2146K9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIROMELATINE

Official Name

English

piromelatine [INN]

Preferred 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

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