{{Short description|Peptide selective agonist of the ghrelin/growth hormone secretagogue receptor}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (2''S'')-6-Amino-2-<nowiki>[[</nowiki>(2''R'')-2-<nowiki>[[</nowiki>(2''R'')-2-<nowiki>[[</nowiki>(2''S'')-2-[(2-amino-2-methylpropanoyl)amino]-3-(4''H''-imidazol-4-yl)propanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanamide. | image = Ipamorelin.svg | image_class = skin-invert-image | width = 250px
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Intravenous, subcutaneous
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = 2 hours<ref name="GobburuAgersø1999">{{cite journal | vauthors = Gobburu JV, Agersø H, Jusko WJ, Ynddal L | title = Pharmacokinetic-pharmacodynamic modeling of ipamorelin, a growth hormone releasing peptide, in human volunteers | journal = Pharmaceutical Research | volume = 16 | issue = 9 | pages = 1412–6 | date = September 1999 | pmid = 10496658 | doi = 10.1023/A:1018955126402 | s2cid = 12048934 }}</ref> | excretion =
<!--Identifiers--> | CAS_number_Ref = | CAS_number = 170851-70-4 | CAS_supplemental = | ATC_prefix = None | ATC_suffix = | PubChem = 20754357 | DrugBank_Ref = | DrugBank = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = Y9M3S784Z6 | ChemSpiderID_Ref = | ChemSpiderID = 8007390
<!--Chemical data--> | C=38 | H=49 | N=9 | O=5 | smiles = CC(C)(C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@H](CC2=CC3=CC=CC=C3C=C2)C(=O)N[C@H](CC4=CC=CC=C4)C(=O)N[C@@H](CCCCN)C(=O)N)N | StdInChI = 1S/C38H49N9O5/c1-38(2,41)37(52)47-32(21-28-22-42-23-43-28)36(51)46-31(20-25-15-16-26-12-6-7-13-27(26)18-25)35(50)45-30(19-24-10-4-3-5-11-24)34(49)44-29(33(40)48)14-8-9-17-39/h3-7,10-13,15-16,18,22-23,29-32H,8-9,14,17,19-21,39,41H2,1-2H3,(H2,40,48)(H,42,43)(H,44,49)(H,45,50)(H,46,51)(H,47,52)/t29-,30+,31+,32-/m0/s1 | StdInChIKey = NEHWBYHLYZGBNO-BVEPWEIPSA-N | synonyms = }}
'''Ipamorelin''' (INN; development code '''NNC 26-0161''') is a peptide selective agonist of the ghrelin/growth hormone secretagogue receptor (GHS) and a growth hormone secretagogue.<ref name="MoulinRyan2007">{{cite journal | vauthors = Moulin A, Ryan J, Martinez J, Fehrentz JA | title = Recent developments in ghrelin receptor ligands | journal = ChemMedChem | volume = 2 | issue = 9 | pages = 1242–59 | date = September 2007 | pmid = 17520591 | doi = 10.1002/cmdc.200700015 | s2cid = 24945528 }}</ref><ref name="RaunHansen1998">{{cite journal | vauthors = Raun K, Hansen BS, Johansen NL, Thøgersen H, Madsen K, Ankersen M, Andersen PH | title = Ipamorelin, the first selective growth hormone secretagogue | journal = European Journal of Endocrinology | volume = 139 | issue = 5 | pages = 552–61 | date = November 1998 | pmid = 9849822 | doi = 10.1530/eje.0.1390552 }}</ref> It is a pentapeptide with the amino acid sequence Aib-His-<small>D</small>-2-Nal-<small>D</small>-Phe-Lys-NH<sub>2</sub> that was derived from GHRP-1.<ref name="IsidroCordido2006">{{cite journal | vauthors = Isidro ML, Cordido F | title = Growth hormone secretagogues | journal = Combinatorial Chemistry & High Throughput Screening | volume = 9 | issue = 3 | pages = 175–80 | date = March 2006 | pmid = 16533150 | doi = 10.2174/138620706776055458 }}</ref>
Ipamorelin significantly increases plasma growth hormone (GH) levels in both animals and humans.<ref name="GobburuAgersø1999" /><ref name="RaunHansen1998" /><ref name="Estrada2002">{{cite journal| vauthors = Jiménez-Reina L, Cañete R, De la Torre MJ, Bernal G |title=Chronic In Vivo Ipamorelin Treatment Stimulates Body Weight Gain and Growth Hormone (GH) Release In Vitro in Young Female Rats|journal=European Journal of Anatomy|volume=6|issue=1|year=2002|pages=37–46|issn=1136-4890|url=https://www.researchgate.net/publication/28093664}}</ref> In addition, ipamorelin stimulates body weight gain in animals.<ref name="Estrada2002" /> Like pralmorelin and GHRP-6, ipamorelin does not affect prolactin, follicle-stimulating hormone (FSH), luteinizing hormone (LH), or thyroid-stimulating hormone (TSH) levels.<ref name="RaunHansen1998" /> However, unlike pralmorelin (GHRP-2) and GHRP-6, but similarly to growth hormone-releasing hormone (GHRH), ipamorelin does not stimulate the secretion of adrenocorticotropic hormone (ACTH), or cortisol, and is highly selective for inducing the secretion only of GH.<ref name="RaunHansen1998" />
Ipamorelin was originally developed by Novo Nordisk, and was investigated in phase II clinical trials by Helsinn Therapeutics for the treatment of postoperative ileus, but was discontinued due to lack of efficacy.<ref name="BeckSweeney2014">{{cite journal | vauthors = Beck DE, Sweeney WB, McCarter MD | title = Prospective, randomized, controlled, proof-of-concept study of the Ghrelin mimetic ipamorelin for the management of postoperative ileus in bowel resection patients | journal = International Journal of Colorectal Disease | volume = 29 | issue = 12 | pages = 1527–34 | date = December 2014 | pmid = 25331030 | doi = 10.1007/s00384-014-2030-8 | s2cid = 22869695 }}</ref><ref name="AdisInsight">{{cite web | url = http://adisinsight.springer.com/drugs/800011351 | title = Ipamorelin | work = AdisInsight | publisher = Springer Nature Switzerland AG | access-date = 10 June 2015}}</ref>
Ipamorelin has been used by athletes as a performance enhancing drug.<ref>{{Cite news | vauthors = Perez AJ | date = 5 May 2016 |url=https://www.usatoday.com/story/sports/mlb/2016/05/04/peptides-mlb--investigation-performance-enhancing-drugs-biogenesis/83915662/|title=Peptides under greater scrutiny in MLB's performance-enhancing drug battle|work=USA TODAY|access-date=2018-04-14|language=en}}</ref><ref>{{Cite news | first = Jack | last = Maloney | name-list-style = vanc | date = 13 April 2018 |url=https://www.cbssports.com/nba/news/nba-playoffs-2018-wizards-jodie-meeks-suspended-25-games-for-failing-drug-test/|title=NBA Playoffs 2018: Wizards' Jodie Meeks suspended 25 games for failing drug test|work=CBSSports.com|access-date=2018-04-14|language=en}}</ref><ref>{{Cite news|url=https://www.nba.com/article/2019/08/29/nets-wilson-chandler-suspended-official-release/|title=Nets' Chandler suspended 25 games for PED use|work=nba.com|access-date=2019-08-30|language=en}}</ref> Currently, Ipamorelin is commonly marketed as a research peptide rather than as an approved pharmaceutical drug. <ref>{{Cite web |title=Ipamorelin |url=https://purepep.co/peptides/Ipamorelin |access-date=2026-01-05 |website=PurePep |language=en}}</ref>
== See also == * List of growth hormone secretagogues
== References == {{Reflist|2}}
== External links ==
{{GH/IGF-1 axis signaling modulators}}
Category:Abandoned drugs Category:Ghrelin receptor agonists Category:Growth hormone secretagogues Category:Imidazoles Category:2-Naphthyl compounds Category:Peptide therapeutics Category:World Anti-Doping Agency prohibited substances