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Piromelatine
Identifiers
	IUPAC name N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-4-oxopyran-2-carboxamide;
CAS Number	946846-83-9;
PubChem CID	24815904;
ChemSpider	32700981;
UNII	S3UN2146K9;
ChEMBL	ChEMBL4297523;
CompTox Dashboard (EPA)	DTXSID90241566 ;
Chemical and physical data
Formula	C17H16N2O4
Molar mass	312.325 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC2=C(C=C1)NC=C2CCNC(=O)C3=CC(=O)C=CO3;
	InChI 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); Key:PNTNBIHOAPJYDB-UHFFFAOYSA-N;

Piromelatine (Neu-P11) is a multimodal sleep drug under development by Neurim Pharmaceuticals. It is an agonist at melatonin MT₁/MT₂ and serotonin 5-HT_1A/5-HT_1D receptors. Neurim is conducting a phase II randomized, placebo controlled trial of cognitive and sleep effects in Alzheimer's disease.

Results of a phase II trial on insomnia in 120 adults were announced in 2013, finding piromelatine 20/50 mg improved sleep over 4 weeks vs placebo.^[1] Phase 1A/1B studies in 2011, showed safe dose-dependent improvement in sleep.^[2] Pre-clinical studies showed antinociceptive^[3] antihypertensive^[4] and cognitive benefits^[5] in rat disease models of pain, hypertension, and Alzheimer's disease.

Antidepressant and anti-anxiety effects were also demonstrated in animal models.^[6]

References

^ "Neurim Pharmaceuticals Announces Positive Phase 2 Clinical Trial Results of Piromelatine for the Treatment of Insomnia". Neurim Pharmaceuticals. 18 February 2013.
^ "Neurim Pharmaceuticals Announces Positive Results From Phase I and Ib Clinical Trials With Neu-p11, a Sleep Maintenance Drug". Neurim Pharmaceuticals. 24 July 2011.
^ Liu YY, Yin D, Chen L, Qu WM, Chen CR, Laudon M, et al. (October 2014). "Piromelatine exerts antinociceptive effect via melatonin, opioid, and 5HT1A receptors and hypnotic effect via melatonin receptors in a mouse model of neuropathic pain". Psychopharmacology. 231 (20): 3973–85. doi:10.1007/s00213-014-3530-5. PMID 24700387. S2CID 815868.
^ Huang L, Zhang C, Hou Y, Laudon M, She M, Yang S, et al. (September 2013). "Blood pressure reducing effects of piromelatine and melatonin in spontaneously hypertensive rats". European Review for Medical and Pharmacological Sciences. 17 (18): 2449–56. PMID 24089222.
^ He P, Ouyang X, Zhou S, Yin W, Tang C, Laudon M, Tian S (June 2013). "A novel melatonin agonist Neu-P11 facilitates memory performance and improves cognitive impairment in a rat model of Alzheimer' disease". Hormones and Behavior. 64 (1): 1–7. doi:10.1016/j.yhbeh.2013.04.009. PMID 23651610. S2CID 205806140.
^ Tian SW, Laudon M, Han L, Gao J, Huang FL, Yang YF, Deng HF (July 2010). "Antidepressant- and anxiolytic effects of the novel melatonin agonist Neu-P11 in rodent models". Acta Pharmacologica Sinica. 31 (7): 775–783. doi:10.1038/aps.2010.80. PMC 4007730. PMID 20581849.