Ipamorelin

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-[[(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;
CompTox Dashboard (EPA)	DTXSID80168955 ;
Chemical and physical data
Formula	C38H49N9O5
Molar mass	711.85296 g/mol g·mol−1
3D 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]

References

^ ^a ^b Gobburu, Jogarao V. S.; Agersø, Henrik; Jusko, William J.; Ynddal, Lars (1999). "Pharmacokinetic-Pharmacodynamic Modeling of Ipamorelin, a Growth Hormone Releasing Peptide, in Human Volunteers". Pharmaceutical Research. 16 (9): 1412–1416. doi:10.1023/A:1018955126402. ISSN 0724-8741.
^ Moulin, Aline; Ryan, Joanne; Martinez, Jean; Fehrentz, Jean-Alain (2007). "Recent Developments in Ghrelin Receptor Ligands". ChemMedChem. 2 (9): 1242–1259. doi:10.1002/cmdc.200700015. ISSN 1860-7179. PMID 17520591.
^ ^a ^b ^c ^d Raun, K; Hansen, B.; Johansen, N.; Thogersen, H; Madsen, K; Ankersen, M; Andersen, P. (1998). "Ipamorelin, the first selective growth hormone secretagogue". European Journal of Endocrinology. 139 (5): 552–561. doi:10.1530/eje.0.1390552. ISSN 0804-4643.
^ Isidro, Maria; Cordido, Fernando (2006). "Growth Hormone Secretagogues". Combinatorial Chemistry & High Throughput Screening. 9 (3): 175–180. doi:10.2174/138620706776055458. ISSN 1386-2073.
^ ^a ^b Estrada, R. Cañete; Jiménez-Reina, L.; de la Torre, M.J.; Bernal, J. (2002). "Chronic In Vivo Ipamorelin Treatment Stimulates Body Weight Gain and Growth Hormone (GH) Release In Vitro in Young Female Rats". 6 (1): 37–46. ISSN 1136-4890. {{cite journal}}: Cite journal requires |journal= (help)
^ Beck, David E.; Sweeney, W. Brian; McCarter, Martin D. (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): 1527–1534. doi:10.1007/s00384-014-2030-8. ISSN 0179-1958.
^ AdisInsight. "Ipamorelin". Retrieved 10 June 2015.

External links

Ipamorelin - AdisInsight

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[GobburuAgersø1999-1] Gobburu, Jogarao V. S.; Agersø, Henrik; Jusko, William J.; Ynddal, Lars (1999). "Pharmacokinetic-Pharmacodynamic Modeling of Ipamorelin, a Growth Hormone Releasing Peptide, in Human Volunteers". Pharmaceutical Research. 16 (9): 1412–1416. doi:10.1023/A:1018955126402. ISSN 0724-8741.

[MoulinRyan2007-2] Moulin, Aline; Ryan, Joanne; Martinez, Jean; Fehrentz, Jean-Alain (2007). "Recent Developments in Ghrelin Receptor Ligands". ChemMedChem. 2 (9): 1242–1259. doi:10.1002/cmdc.200700015. ISSN 1860-7179. PMID 17520591.

[RaunHansen1998-3] Raun, K; Hansen, B.; Johansen, N.; Thogersen, H; Madsen, K; Ankersen, M; Andersen, P. (1998). "Ipamorelin, the first selective growth hormone secretagogue". European Journal of Endocrinology. 139 (5): 552–561. doi:10.1530/eje.0.1390552. ISSN 0804-4643.

[IsidroCordido2006-4] Isidro, Maria; Cordido, Fernando (2006). "Growth Hormone Secretagogues". Combinatorial Chemistry & High Throughput Screening. 9 (3): 175–180. doi:10.2174/138620706776055458. ISSN 1386-2073.

[Estrada2002-5] Estrada, R. Cañete; Jiménez-Reina, L.; de la Torre, M.J.; Bernal, J. (2002). "Chronic In Vivo Ipamorelin Treatment Stimulates Body Weight Gain and Growth Hormone (GH) Release In Vitro in Young Female Rats". 6 (1): 37–46. ISSN 1136-4890. {{cite journal}}: Cite journal requires |journal= (help)

[BeckSweeney2014-6] Beck, David E.; Sweeney, W. Brian; McCarter, Martin D. (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): 1527–1534. doi:10.1007/s00384-014-2030-8. ISSN 0179-1958.

[AdisInsight-7] AdisInsight. "Ipamorelin". Retrieved 10 June 2015.

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See also

References

External links