Piromelatine

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.

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
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

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.

See also

• List of investigational sleep drugs

References

1. "Neurim Pharmaceuticals Announces Positive Phase 2 Clinical Trial Results of Piromelatine for the Treatment of Insomnia". Neurim Pharmaceuticals. 18 February 2013.
2. "Neurim Pharmaceuticals Announces Positive Results From Phase I and Ib Clinical Trials With Neu-p11, a Sleep Maintenance Drug". Neurim Pharmaceuticals. 24 July 2011.
3. 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.
4. 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.
5. 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.