# Ipamorelin

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Ipamorelin
> Markdown URL: https://mediated.wiki/source/Ipamorelin.md
> Source: https://en.wikipedia.org/wiki/Ipamorelin
> Source revision: 1331220056
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/Intravenous), [subcutaneous](/source/subcutaneous_injection)

<!--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](/source/International_Nonproprietary_Name); development code '''NNC 26-0161''') is a [peptide](/source/peptide) selective [agonist](/source/agonist) of the [ghrelin/growth hormone secretagogue receptor](/source/growth_hormone_secretagogue_receptor) (GHS) and a [growth hormone secretagogue](/source/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](/source/pentapeptide_(oligopeptide)) with the [amino acid sequence](/source/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](/source/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](/source/Blood_plasma) [growth hormone](/source/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](/source/GHRP-6)-6, ipamorelin does not affect [prolactin](/source/prolactin), [follicle-stimulating hormone](/source/follicle-stimulating_hormone) (FSH), [luteinizing hormone](/source/luteinizing_hormone) (LH), or [thyroid-stimulating hormone](/source/thyroid-stimulating_hormone) (TSH) levels.<ref name="RaunHansen1998" /> However, unlike [pralmorelin](/source/pralmorelin) (GHRP-2) and [GHRP-6](/source/GHRP-6), but similarly to [growth hormone-releasing hormone](/source/growth_hormone-releasing_hormone) (GHRH), ipamorelin does not stimulate the secretion of [adrenocorticotropic hormone](/source/adrenocorticotropic_hormone) (ACTH), or [cortisol](/source/cortisol), and is highly selective for inducing the secretion only of GH.<ref name="RaunHansen1998" />

Ipamorelin was originally developed by [Novo Nordisk](/source/Novo_Nordisk), and was investigated in [phase II](/source/Phases_of_clinical_research) [clinical trial](/source/clinical_trial)s by [Helsinn Therapeutics](/source/Helsinn_Therapeutics) for the treatment of [postoperative ileus](/source/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](/source/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](/source/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

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Adapted from the Wikipedia article [Ipamorelin](https://en.wikipedia.org/wiki/Ipamorelin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Ipamorelin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.