Relamorelin

Relamorelin (INN, USAN) (developmental code names RM-131, BIM-28131, BIM-28163) is a synthetic peptide, centrally penetrant, selective agonist of the ghrelin/growth hormone secretagogue receptor (GHSR) which is under development by Allergan pharmaceuticals for the treatment of diabetic gastroparesis, chronic idiopathic constipation, and anorexia nervosa.[1][2][3] It is a pentapeptide and an analogue of ghrelin with improved potency and pharmacokinetics.[1][2] In humans, relamorelin produces increases in plasma growth hormone, prolactin, and cortisol levels,[2][4] and, like other GHSR agonists, increases appetite.[3] As of June 2015, relamorelin is in phase II clinical trials for diabetic gastroparesis and constipation.[5] The United States Food and Drug Administration (FDA) has granted Fast Track designation to relamorelin for diabetic gastroparesis.[6]

Relamorelin
Clinical data
Routes of
administration		Subcutaneous
ATC code
  • None
Identifiers
IUPAC name
  • 4-[[(2S)-2-[[(2R)-2-[[(2R)-3-(1-Benzothiophen-3-yl)-2-(piperidine-3-carbonylamino)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]piperidine-4-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC43H50N8O5S
Molar mass790.98 g·mol−1
3D model (JSmol)
SMILES
  • c1ccc(cc1)C[C@@H](C(=O)NC2(CCNCC2)C(=O)N)NC(=O)[C@@H](Cc3c[nH]c4c3cccc4)NC(=O)[C@@H](Cc5csc6c5cccc6)NC(=O)C7CCNCC7
InChI
  • InChI=1S/C43H50N8O5S/c44-42(56)43(16-20-46-21-17-43)51-41(55)34(22-27-8-2-1-3-9-27)49-39(53)35(23-29-25-47-33-12-6-4-10-31(29)33)50-40(54)36(48-38(52)28-14-18-45-19-15-28)24-30-26-57-37-13-7-5-11-32(30)37/h1-13,25-26,28,34-36,45-47H,14-24H2,(H2,44,56)(H,48,52)(H,49,53)(H,50,54)(H,51,55)/t34-,35+,36+/m0/s1
  • Key:KUBPNVYPKPWGRJ-LIVOIKKVSA-N

See also

References
  1. Haddley K (2014). "Relamorelin. Ghrelin receptor agonist, treatment of constipation, treatment of anorexia nervosa, treatment of diabetic gastroparesis". Drugs of the Future. 39 (11): 775. doi:10.1358/dof.2014.039.011.2231856. ISSN 0377-8282.
  2. Camilleri M, Acosta A (March 2015). "Emerging treatments in Neurogastroenterology: relamorelin: a novel gastrocolokinetic synthetic ghrelin agonist". Neurogastroenterology and Motility. 27 (3): 324–32. doi:10.1111/nmo.12490. PMC 4424792. PMID 25545036.
  3. Acosta A, Camilleri M, Kolar G, Iturrino J, Szarka LA, Boldingh A, et al. (December 2015). "Relamorelin Relieves Constipation and Accelerates Colonic Transit in a Phase 2, Placebo-Controlled, Randomized Trial". Clinical Gastroenterology and Hepatology. 13 (13): 2312–9.e1. doi:10.1016/j.cgh.2015.04.184. PMID 26001337.
  4. Shin A, Camilleri M, Busciglio I, Burton D, Stoner E, Noonan P, et al. (January 2013). "Randomized controlled phase Ib study of ghrelin agonist, RM-131, in type 2 diabetic women with delayed gastric emptying: pharmacokinetics and pharmacodynamics". Diabetes Care. 36 (1): 41–8. doi:10.2337/dc12-1128. PMC 3526234. PMID 22961573.
  5. Valentin N, Acosta A, Camilleri M (June 2015). "Early investigational therapeutics for gastrointestinal motility disorders: from animal studies to Phase II trials". Expert Opinion on Investigational Drugs. 24 (6): 769–79. doi:10.1517/13543784.2015.1025132. PMC 4578705. PMID 25971881.
  6. Rhythm Pharmaceuticals (2014). "Rhythm Presents Positive Phase 2 Study Results for Relamorelin for Chronic Constipation". PRNewsire. Retrieved June 10, 2015.
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