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Ipamorelin

From Wikipedia, the free encyclopedia
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
Eliminationhalf-life2 hours[1]
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC38H49N9O5
Molar mass711.868 g·mol−1
3D model (JSmol)
  • 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=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 nameNNC 26-0161) is apeptide selectiveagonist of theghrelin/growth hormone secretagogue receptor (GHS) and agrowth hormone secretagogue.[2][3] It is apentapeptide with theamino acid sequence Aib-His-D-2-Nal-D-Phe-Lys-NH2 that was derived fromGHRP-1.[4]

Ipamorelin significantly increasesplasmagrowth hormone (GH) levels in both animals and humans.[1][3][5] In addition, ipamorelin stimulates body weight gain in animals.[5] Like pralmorelin andGHRP-6, ipamorelin does not affectprolactin,follicle-stimulating hormone (FSH),luteinizing hormone (LH), orthyroid-stimulating hormone (TSH) levels.[3] However, unlikepralmorelin (GHRP-2) andGHRP-6, but similarly togrowth hormone-releasing hormone (GHRH), ipamorelin does not stimulate the secretion ofadrenocorticotropic hormone (ACTH), orcortisol, and is highly selective for inducing the secretion only of GH.[3]

Ipamorelin was originally developed byNovo Nordisk, and was investigated inphase IIclinical trials byHelsinn Therapeutics for the treatment ofpostoperative ileus, but was discontinued due to lack of efficacy.[6][7]

Ipamorelin has been used by athletes as aperformance enhancing drug.[8][9][10]

See also

[edit]

References

[edit]
  1. ^abGobburu 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.
  2. ^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.
  3. ^abcdRaun 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.
  4. ^Isidro ML, Cordido F (March 2006). "Growth hormone secretagogues".Combinatorial Chemistry & High Throughput Screening.9 (3):175–80.doi:10.2174/138620706776055458.PMID 16533150.
  5. ^abJiménez-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.
  6. ^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.
  7. ^"Ipamorelin".AdisInsight. Springer Nature Switzerland AG. Retrieved10 June 2015.
  8. ^Perez AJ (5 May 2016)."Peptides under greater scrutiny in MLB's performance-enhancing drug battle".USA TODAY. Retrieved2018-04-14.
  9. ^Maloney J (13 April 2018)."NBA Playoffs 2018: Wizards' Jodie Meeks suspended 25 games for failing drug test".CBSSports.com. Retrieved2018-04-14.
  10. ^"Nets' Chandler suspended 25 games for PED use".nba.com. Retrieved2019-08-30.

External links

[edit]
GH
(somatotropin)
GHIH
(somatostatin)
GHRH
(somatocrinin)
GHS
(ghrelin)
IGF-1
(somatomedin)
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