pralmorelin

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = (2S)-6-Amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-aminopropanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide

| image = Pralmorelin.svg

| width = 250

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| routes_of_administration = Oral, intravenous

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| CAS_number = 158861-67-7

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = E6S6E1F19M

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| PubChem = 6852372

| IUPHAR_ligand = 1092

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| ChemSpiderID = 5293451

| C=45 | H=55 | N=9 | O=6

| smiles = C[C@H](C(=O)N[C@H](CC1=CC2=CC=CC=C2C=C1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@H](CC5=CC=CC=C5)C(=O)N[C@@H](CCCCN)C(=O)N)N

| StdInChI = 1S/C45H55N9O6/c1-27(47)41(56)52-38(24-30-19-20-31-14-6-7-15-32(31)22-30)43(58)50-28(2)42(57)53-39(25-33-26-49-35-17-9-8-16-34(33)35)45(60)54-37(23-29-12-4-3-5-13-29)44(59)51-36(40(48)55)18-10-11-21-46/h3-9,12-17,19-20,22,26-28,36-39,49H,10-11,18,21,23-25,46-47H2,1-2H3,(H2,48,55)(H,50,58)(H,51,59)(H,52,56)(H,53,57)(H,54,60)/t27-,28+,36+,37-,38-,39+/m1/s1

| StdInChIKey = HRNLPPBUBKMZMT-RDRUQFPZSA-N

| synonyms = D-Alanyl-3-(naphthalen-2-yl)-D-alanyl-L-alanyl-L-tryptophyl-D-phenylalanyl-L-lysinamide

}}

Pralmorelin (INN) (brand name GHRP Kaken 100; former developmental code names KP-102, GPA-748, WAY-GPA-748), also known as pralmorelin hydrochloride (JAN) and pralmorelin dihydrochloride (USAN), as well as, notably, growth hormone-releasing peptide 2 (GHRP-2), is a growth hormone secretagogue (GHS) used as a diagnostic agent that is marketed by Kaken Pharmaceutical in Japan in a single-dose formulation for the assessment of growth hormone deficiency (GHD).{{cite journal| vauthors = Graul AI, Prous JR |title=The Year's New Drugs: A Historical and Research Perspective on the 41 New Products that Reached their First Markets in 2005|journal=Drug News & Perspectives|volume=19|issue=1|year=2006|page=33|issn=0214-0934|url=https://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=3&p_RefId=2990&p_IsPs=Y}}{{cite journal| vauthors = Moulin A, Brunel L, Verdié P, Gavara L, Martinez J, Fehrentz JA |title=Ghrelin Receptor Ligands: Design and Synthesis of Pseudopeptides and Peptidomimetics|journal=Current Chemical Biology|volume=7|issue=3|year=2014|pages=254–270|issn=2212-7968|doi=10.2174/2212796807999131128125920}}{{cite book | vauthors = Jameson JL, De Groot LJ |title=Endocrinology: Adult and Pediatric: Expert Consult - Online|url=https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PT1366|date=25 February 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-32195-2|pages=1366–}}

Pralmorelin is an orally-active, synthetic peptide drug, specifically, an analogue of met-enkephalin, with the amino acid sequence D-Ala-D-(β-naphthyl)-Ala-Trp-D-Phe-Lys-NH₂.{{cite journal | vauthors = ((Adis Editorial)) | title = Pralmorelin: GHRP 2, GPA 748, growth hormone-releasing peptide 2, KP-102 D, KP-102 LN, KP-102D, KP-102LN | journal = Drugs in R&D | volume = 5 | issue = 4 | pages = 236–239 | year = 2004 | pmid = 15230633 | doi = 10.2165/00126839-200405040-00011 }} It acts as a ghrelin/growth hormone secretagogue receptor (GHSR) agonist, and was the first of this class of drugs to be introduced clinically. Acute administration of the drug markedly increases the levels of plasma growth hormone (GH){{cite journal | vauthors = Furuta S, Shimada O, Doi N, Ukai K, Nakagawa T, Watanabe J, Imaizumi M | title = General pharmacology of KP-102 (GHRP-2), a potent growth hormone-releasing peptide | journal = Arzneimittel-Forschung | volume = 54 | issue = 12 | pages = 868–880 | year = 2004 | pmid = 15646371 | doi = 10.1055/s-0031-1297042 | s2cid = 28632234 }} and reliably induces sensations of hunger and increases food intake in humans.{{cite journal | vauthors = Müller TD, Nogueiras R, Andermann ML, Andrews ZB, Anker SD, Argente J, Batterham RL, Benoit SC, Bowers CY, Broglio F, Casanueva FF, D'Alessio D, Depoortere I, Geliebter A, Ghigo E, Cole PA, Cowley M, Cummings DE, Dagher A, Diano S, Dickson SL, Diéguez C, Granata R, Grill HJ, Grove K, Habegger KM, Heppner K, Heiman ML, Holsen L, Holst B, Inui A, Jansson JO, Kirchner H, Korbonits M, Laferrère B, LeRoux CW, Lopez M, Morin S, Nakazato M, Nass R, Perez-Tilve D, Pfluger PT, Schwartz TW, Seeley RJ, Sleeman M, Sun Y, Sussel L, Tong J, Thorner MO, van der Lely AJ, van der Ploeg LH, Zigman JM, Kojima M, Kangawa K, Smith RG, Horvath T, Tschöp MH | display-authors = 6 | title = Ghrelin | journal = Molecular Metabolism | volume = 4 | issue = 6 | pages = 437–460 | date = June 2015 | pmid = 26042199 | pmc = 4443295 | doi = 10.1016/j.molmet.2015.03.005 }}

Pralmorelin was also under investigation for the treatment of GHD and short stature (pituitary dwarfism), and made it to phase II clinical trials for these indications, but was ultimately never marketed for them. This may be because the ability of pralmorelin to increase plasma GH levels is significantly lower in people with GHD relative to healthy individuals.