Ipamorelin

Peptide selective agonist of the ghrelin/growth hormone secretagogue receptor

None

Pharmacokinetic dataElimination half-life2 hours^[1]Identifiers

IUPAC name

(2S)-6-Amino-2-[[(2R)-2-[[(2R)-2-[[(2S)-2-[(2-amino-2-methylpropanoyl)amino]-3-(4H-imidazol-4-yl)propanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanamide.

CAS Number

170851-70-4

PubChem CID

20754357

ChemSpider

8007390

UNII

Y9M3S784Z6

CompTox Dashboard (EPA)

DTXSID80168955

Chemical and physical dataFormulaC₃₈H₄₉N₉O₅Molar mass711.868 g·mol⁻¹3D model (JSmol)

Interactive image

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

InChI

InChI=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
Key:NEHWBYHLYZGBNO-BVEPWEIPSA-N

Ipamorelin (INN) (developmental code name NNC 26-0161) is a peptide selective agonist of the ghrelin/growth hormone secretagogue receptor (GHS) and a growth hormone secretagogue.^[2]^[3] It is a pentapeptide with the amino acid sequence Aib-His-D-2-Nal-D-Phe-Lys-NH₂ that was derived from GHRP-1.^[4]

Ipamorelin significantly increases plasma growth hormone (GH) levels in both animals and humans.^[1]^[3]^[5] In addition, ipamorelin stimulates body weight gain in animals.^[5] Like pralmorelin and GHRP-6, ipamorelin does not affect prolactin, follicle-stimulating hormone (FSH), luteinizing hormone (LH), or thyroid-stimulating hormone (TSH) levels.^[3] 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.^[3]

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.^[6]^[7]

Ipamorelin has been used by athletes as a performance enhancing drug.^[8]^[9]^[10]

References

^ ^a ^b Gobburu JV, Agersø H, Jusko WJ, Ynddal L (September 1999). "Pharmacokinetic-pharmacodynamic modeling of ipamorelin, a growth hormone releasing peptide, in human volunteers". Pharmaceutical Research. 16 (9): 1412–6. doi:10.1023/A:1018955126402. PMID 10496658. S2CID 12048934.
^ Moulin A, Ryan J, Martinez J, Fehrentz JA (September 2007). "Recent developments in ghrelin receptor ligands". ChemMedChem. 2 (9): 1242–59. doi:10.1002/cmdc.200700015. PMID 17520591. S2CID 24945528.
^ ^a ^b ^c ^d Raun K, Hansen BS, Johansen NL, Thøgersen H, Madsen K, Ankersen M, Andersen PH (November 1998). "Ipamorelin, the first selective growth hormone secretagogue". European Journal of Endocrinology. 139 (5): 552–61. doi:10.1530/eje.0.1390552. PMID 9849822.
^ Isidro ML, Cordido F (March 2006). "Growth hormone secretagogues". Combinatorial Chemistry & High Throughput Screening. 9 (3): 175–80. doi:10.2174/138620706776055458. PMID 16533150.
^ ^a ^b Jiménez-Reina L, Cañete R, De la Torre MJ, Bernal G (2002). "Chronic In Vivo Ipamorelin Treatment Stimulates Body Weight Gain and Growth Hormone (GH) Release In Vitro in Young Female Rats". European Journal of Anatomy. 6 (1): 37–46. ISSN 1136-4890.
^ Beck DE, Sweeney WB, McCarter MD (December 2014). "Prospective, randomized, controlled, proof-of-concept study of the Ghrelin mimetic ipamorelin for the management of postoperative ileus in bowel resection patients". International Journal of Colorectal Disease. 29 (12): 1527–34. doi:10.1007/s00384-014-2030-8. PMID 25331030. S2CID 22869695.
^ "Ipamorelin". AdisInsight. Springer Nature Switzerland AG. Retrieved 10 June 2015.
^ Perez AJ (5 May 2016). "Peptides under greater scrutiny in MLB's performance-enhancing drug battle". USA TODAY. Retrieved 2018-04-14.
^ Maloney J (13 April 2018). "NBA Playoffs 2018: Wizards' Jodie Meeks suspended 25 games for failing drug test". CBSSports.com. Retrieved 2018-04-14.
^ "Nets' Chandler suspended 25 games for PED use". nba.com. Retrieved 2019-08-30.