Relamorelin

Names

[ Name ]:
Relamorelin

[Synonym ]:
3-(1-Benzothiophen-3-yl)-N-(4-piperidinylcarbonyl)-D-alanyltryptophyl-N-(4-carbamoyl-4-piperidinyl)phenylalaninamide
Phenylalaninamide, 3-benzo[b]thien-3-yl-N-(4-piperidinylcarbonyl)-D-alanyltryptophyl-N-[4-(aminocarbonyl)-4-piperidinyl]-
Relamorelin
UNII-BIW199E18V
BIW199E18V
[3-(1-benzothiophen-3-yl)-N-(piperidin-4-ylcarbonyl)-D-alanyl]-D-tryptophyl-L-phenylalanyl-(4-aminopiperidine-4-carboxamide)
3-(1-Benzothiophen-3-yl)-N-(4-piperidinylcarbonyl)-D-alanyl-D-tryptophyl-N-(4-carbamoyl-4-piperidinyl)-L-phenylalaninamide
L-Phenylalaninamide, 3-benzo[b]thien-3-yl-N-(4-piperidinylcarbonyl)-D-alanyl-D-tryptophyl-N-[4-(aminocarbonyl)-4-piperidinyl]-

Biological Activity

[Description]:

Relamorelin (RM-131), a Ghrelin analog, is a potent ghrelin receptor agonist, with a Ki of 0.42 nM for GHS-1a. Relamorelin can promote food intake and adiposity in mice. Relamorelin can be used for the research of cachexia, gastroparesis, and gastric/intestinal dysmobility disorders[1][2][3].

[Related Catalog]:

Research Areas >> Metabolic Disease

Signaling Pathways >> GPCR/G Protein >> GHSR

[Target]

Ki: 0.42 nM (GHS-1a)[1]

[In Vitro]

Relamorelin shows ∼3 times greater affinity for GHS-1a (Ki=0.42 nM) than native ghrelin (Ki=1. 12 nM)[1]. Relamorelin is 6 times more potent (EC50=0.71 nM) in activating the GHS-1a receptor than native ghrelin (EC50=4.2 nM) as assessed in vitro by calcium mobilization[1].

[In Vivo]

Relamorelin (500 nmol/kg/day; continuous infusion for 5 days) increases the food intake and weight gain in rats[1]. Relamorelin (50-500 nmol/kg/day; continuous infusion for 5 days) decreases the loss of body mass and fat mass[1]. RM-131 (250-500 nmol/kg; a single s.c.) stimulates acute food intake in wt but not growth hormone secretagogue receptor (GHR) ko mice[2]. Animal Model: F344/NTacfBR male rats implanted with tumor[1] Dosage: 50, 500 nmol/kg/day Administration: Continuous infusion at a rate of 0.5 μL/h for 5 d s.c. Result: Resulted in an increase in food intake (tumor/saline 41.4 g, tumor/BIM-28131 72.5 g) and weight gain (tumor/saline -10.3%, tumor/BIM-28131 +19.5%).

[References]

[1]. DeBoer MD, et, al. Ghrelin treatment causes increased food intake and retention of lean body mass in a rat model of cancer cachexia. Endocrinology. 2007 Jun;148(6):3004-12.

[2]. Fischer K, et, al. The Pentapeptide RM-131 Promotes Food Intake and Adiposity in Wildtype Mice but Not in Mice Lacking the Ghrelin Receptor. Front Nutr. 2015 Jan 12;1:31.

[3]. Zatorski H, et, al. Relamorelin and other ghrelin receptor agonists - future options for gastroparesis, functional dyspepsia and proton pump inhibitors-resistant non-erosive reflux disease. J Physiol Pharmacol. 2017 Dec;68(6):797-805.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
1216.2±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₃H₅₀N₈O₅S

[ Molecular Weight ]:
790.973

[ Flash Point ]:
689.3±34.3 °C

[ Exact Mass ]:
790.362488

[ LogP ]:
5.22

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.692

Related Compounds

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