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
Current Phase II investigational therapies for insomnia.	2015 Mar	25423562
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
Melatonin, but not melatonin receptor agonists Neu-P11 and Neu-P67, attenuates TNBS-induced colitis in mice.	2016 May	26899972
Inflammaging, Metabolic Syndrome and Melatonin: A Call for Treatment Studies.	2017	27165273
Neu-P11, a novel MT1/MT2 agonist, reverses diabetes by suppressing the hypothalamic-pituitary-adrenal axis in rats.	2017 Oct 5	28687198
Circadian Rhythm and Melatonin in the Treatment of Depression.	2018	30073921
Melatonin Receptor Agonist Piromelatine Ameliorates Impaired Glucose Metabolism in Chronically Stressed Rats Fed a High-Fat Diet.	2018 Jan	29025979
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 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