Ipamorelin

From Wikipedia, the free encyclopedia
Ipamorelin
Ipamorelin.svg
Clinical data
Routes of
administration		Intravenous, subcutaneous
ATC code
  • None
Pharmacokinetic data
Elimination half-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
PubChem CID
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 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 .[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 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]

See also[]

References[]

  1. ^ 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.
  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. ^ 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.
  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. ^ 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.
  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. Retrieved 10 June 2015.
  8. ^ Perez AJ (5 May 2016). "Peptides under greater scrutiny in MLB's performance-enhancing drug battle". USA TODAY. Retrieved 2018-04-14.
  9. ^ Maloney J (13 April 2018). "NBA Playoffs 2018: Wizards' Jodie Meeks suspended 25 games for failing drug test". CBSSports.com. Retrieved 2018-04-14.
  10. ^ "Nets' Chandler suspended 25 games for PED use". nba.com. Retrieved 2019-08-30.

External links[]

Stub icon

This hormonal preparation article is a stub. You can help Wikipedia by .

  • v
  • t
Retrieved from ""