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 reduces clock/apelin expression in insulin-resistant mouse adipocyte model.	2013 Sep	23963596
Exploration on mechanism of a new type of melatonin receptor agonist Neu-p11 in hypoxia-reoxygenation injury of myocardial cells.	2014 Nov	24840226
Neuroprotective mechanism of the novel melatonin derivative Neu-P11 in brain ischemia related models.	2015 Dec	26188145
Melatonin and Synthetic Melatoninergic Agonists in Psychiatric and Age-associated Disorders: Successful and Unsuccessful Approaches.	2016	25248806
Piromelatine ameliorates memory deficits associated with chronic mild stress-induced anhedonia in rats.	2016 Jun	27007604
Role of Neu-p11/luzindole in the regulation of insulin signaling pathways and insulin resistance.	2016 May	27025603
Inflammaging, Metabolic Syndrome and Melatonin: A Call for Treatment Studies.	2017	27165273
Circadian Rhythm and Melatonin in the Treatment of Depression.	2018	30073921

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:21:56 GMT 2023` Edited by `admin` on `Sat Dec 16 01:21:56 GMT 2023`
Record UNII	S3UN2146K9
Record Status	`Validated (UNII)`
Record Version

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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