Ipamorelin - Misplaced Pages

Peptide selective agonist of the ghrelin/growth hormone secretagogue receptor Pharmaceutical compound

Ipamorelin
Clinical data

Routes of administration	Intravenous, subcutaneous
ATC code	None
Pharmacokinetic data
Elimination half-life	2 hours
Identifiers
IUPAC name (2S)-6-Amino-2--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 data
Formula	C₃₈H₄₉N₉O₅
Molar mass	711.868 g·mol
3D model (JSmol)	Interactive image
SMILES CC(C)(C(=O)N(CC1=CNC=N1)C(=O)N(CC2=CC3=CC=CC=C3C=C2)C(=O)N(CC4=CC=CC=C4)C(=O)N(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. It is a pentapeptide with the amino acid sequence Aib-His-D-2-Nal-D-Phe-Lys-NH₂ that was derived from GHRP-1.

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

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.

Ipamorelin has been used by athletes as a performance enhancing drug.

References

^ 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.
^ 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.
^ 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.

External links

v t e GH/IGF-1 axis signaling modulators
GH (somatotropin)	Agonists: Albusomatropin Bovine somatotropin Efpegsomatropin Eftansomatropin alfa Growth hormone Human placental lactogen Lonapegsomatropin Placental growth hormone (growth hormone variant) Somagrebove Somapacitan Somatosalm Somatotropin Somatropin pegol Somatrem Sometribove Somatrogon (MOD-4023; hGH-CTP) Somavaratan Somavubove Somidobove Antagonists: G120K-hGH Pegvisomant Antisense oligonucleotides: Atesidorsen Binding proteins: GHBPTooltip Growth hormone-binding protein
GHIH (somatostatin)	Agonists: BIM-23052 CH-275 Cortistatin-14 Depreotide Edotreotide Ilatreotide L-803,087 L-817,818 Lanreotide NNC 26-9100 Octreotate Octreotide Pasireotide Pentetreotide RC-160 Seglitide Somatostatin (GHIH) Somatostatin (1-28) SRIF-14 SRIF-28 TT-232 Vapreotide Veldoreotide Antagonists: BIM-23056 Cyclosomatostatin CYN-154806 Satoreotide
GHRH (somatocrinin)	Agonists: Peptide: ALRN-5281 CJC-1295 Dumorelin GHRH Modified GRF (1-29) Rismorelin Sermorelin Somatorelin Tesamorelin Antagonists: MZ-5-156
GHS (ghrelin)	Agonists: Peptide: Alexamorelin Cortistatin-14 EP-51216 Examorelin (hexarelin) Ghrelin GHRP-1 GHRP-3 GHRP-4 GHRP-5 GHRP-6 Ipamorelin Lenomorelin Livoletide LY-444711 Pralmorelin (GHRP-2) Relamorelin Tabimorelin Ulimorelin; Non-peptide: Adenosine Anamorelin Capromorelin CP-464709 Ibutamoren (MK-677) L-692,585 Macimorelin SM-130686; Unsorted: LY-426410 LY-444711 Antagonists: A-778193 Cortistatin-8 (D-Lys³)-GHRP-6 JMV2959 YIL-781
IGF-1 (somatomedin)	See here instead.

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