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Peptide selective agonist of the ghrelin/growth hormone secretagogue receptor
Ipamorelin
Routes of administration
Intravenous ,
subcutaneous
ATC code
Elimination half-life 2 hours
[1]
(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 )
Formula C 38 H 49 N 9 O 5
Molar mass 711.868 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
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]
See also
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 .
External links