PIROMELATINE

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=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

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
NEU-P11, a novel melatonin agonist, inhibits weight gain and improves insulin sensitivity in high-fat/high-sucrose-fed rats.	2009 Apr	19429466
Piromelatine, a novel melatonin receptor agonist, stabilizes metabolic profiles and ameliorates insulin resistance in chronic sleep restricted rats.	2014 Mar 15	24486392
Melatonin and Synthetic Melatoninergic Agonists in Psychiatric and Age-associated Disorders: Successful and Unsuccessful Approaches.	2016	25248806
Anticonvulsant activity of melatonin, but not melatonin receptor agonists Neu-P11 and Neu-P67, in mice.	2016 Jul 1	27016427
Role of Neu-p11/luzindole in the regulation of insulin signaling pathways and insulin resistance.	2016 May	27025603
Neu-P11, a novel MT1/MT2 agonist, reverses diabetes by suppressing the hypothalamic-pituitary-adrenal axis in rats.	2017 Oct 5	28687198
Insomnia in Elderly Patients: Recommendations for Pharmacological Management.	2018 Sep	30058034

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

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