Macimorelin Acetate

• CAT Number: I031438
• CAS Number: 945212-59-9
• Molecular Formula: C28H34N6O5
• Molecular Weight: 534.62
• Purity: 98%
• Synonyms: ARD 07 acetate; ARD-07; ARD07; D-87575 acetate; JMV1843; JMV-1843; JMV 1843; AEZS-130; AEZS 130; AEZS130; EP-1572; EP 1572; EP1572; UMV-1843; UMV1843; UMV 1843; Macimorelin; AibDTrpDgTrpCHO. Macimorelin Acetate; Macrilen
• Target: GHSR
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2-Amino-N-[(2R)-1-[[(1R)-1-formamido-2-(1H-indol-3-yl)ethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-methylpropanamide acetate
• InChI: InChI=1S/C26H30N6O3.C2H4O2/c1-26(2,27)25(35)31-22(11-16-13-28-20-9-5-3-7-18(16)20)24(34)32-23(30-15-33)12-17-14-29-21-10-6-4-8-19(17)21;1-2(3)4/h3-10,13-15,22-23,28-29H,11-12,27H2,1-2H3,(H,30,33)(H,31,35)(H,32,34);1H3,(H,3,4)/t22-,23-;/m1./s1
• InChIKey: WVDSKQXKCDZXLH-OHIDFYLOSA-N
• SMILES: CC(C)(N)C(N[C@H](CC1=CNC2=C1C=CC=C2)C(N[C@@H](NC=O)CC3=CNC4=C3C=CC=C4)=O)=O.CC(O)=O

Macimorelin Acetate (Cat.No:I031438) is a synthetic peptide analog used in the diagnosis of growth hormone deficiency (GHD) in adults. It acts as a growth hormone secretagogue, stimulating the release of growth hormone from the pituitary gland. Macimorelin Acetate is administered orally and provides a convenient and reliable method for GHD testing.

Reference

1: Yuen KCJ, Llahana S, Miller BS. Adult growth hormone deficiency: clinical advances and approaches to improve adherence. Expert Rev Endocrinol Metab. 2019 Nov 13:1-18. doi: 10.1080/17446651.2019.1689119. [Epub ahead of print] PubMed PMID: 31721610.
2: Buckinx A, Van Den Herrewegen Y, Pierre A, Cottone E, Ben Haj Salah K, Fehrentz JA, Kooijman R, De Bundel D, Smolders I. Differential Effects of a Full and Biased Ghrelin Receptor Agonist in a Mouse Kindling Model. Int J Mol Sci. 2019 May 20;20(10). pii: E2480. doi: 10.3390/ijms20102480. PubMed PMID: 31137460; PubMed Central PMCID: PMC6567032.
3: Ryabets-Lienhard A, Akhtar S, Monzavi R, Austin J. Meeting Report: 2018 Annual Meeting of the Pediatric Endocrine Society, Toronto, Canada, May 5-8, 2018, Selected Highlights. Pediatr Endocrinol Rev. 2018 Dec;16(2):284-293. doi: 10.17458/per.vol16.2018.lama.mr.pestoronto. PubMed PMID: 30556661.
4: Garcia JM, Biller BMK, Korbonits M, Popovic V, Luger A, Strasburger CJ, Chanson P, Medic-Stojanoska M, Schopohl J, Zakrzewska A, Pekic S, Bolanowski M, Swerdloff R, Wang C, Blevins T, Marcelli M, Ammer N, Sachse R, Yuen KCJ. Macimorelin as a Diagnostic Test for Adult GH Deficiency. J Clin Endocrinol Metab. 2018 Aug 1;103(8):3083-3093. doi: 10.1210/jc.2018-00665. PubMed PMID: 29860473.
5: Yuen KCJ. Growth Hormone Stimulation Tests in Assessing Adult Growth Hormone Deficiency. 2019 Nov 1. In: Feingold KR, Anawalt B, Boyce A, Chrousos G, Dungan K, Grossman A, Hershman JM, Kaltsas G, Koch C, Kopp P, Korbonits M, McLachlan R, Morley JE, New M, Perreault L, Purnell J, Rebar R, Singer F, Trence DL, Vinik A, Wilson DP, editors. Endotext [Internet]. South Dartmouth (MA): MDText.com, Inc.; 2000-. Available from http://www.ncbi.nlm.nih.gov/books/NBK395585/ PubMed PMID: 27809446.
6: Coppens J, Aourz N, Walrave L, Fehrentz JA, Martinez J, De Bundel D, Portelli J, Smolders I. Anticonvulsant effect of a ghrelin receptor agonist in 6Hz corneally kindled mice. Epilepsia. 2016 Sep;57(9):e195-9. doi: 10.1111/epi.13463. Epub 2016 Jul 5. PubMed PMID: 27378373.
7: Maingot M, Blayo AL, Denoyelle S, M’Kadmi C, Damian M, Mary S, Gagne D, Sanchez P, Aicher B, Schmidt P, Müller G, Teifel M, Günther E, Marie J, Banères JL, Martinez J, Fehrentz JA. New ligands of the ghrelin receptor based on the 1,2,4-triazole scaffold by introduction of a second chiral center. Bioorg Med Chem Lett. 2016 May 15;26(10):2408-2412. doi: 10.1016/j.bmcl.2016.04.003. Epub 2016 Apr 4. PubMed PMID: 27072910.
8: Agrawal V, Garcia JM. The macimorelin-stimulated growth hormone test for adult growth hormone deficiency diagnosis. Expert Rev Mol Diagn. 2014 Jul;14(6):647-54. doi: 10.1586/14737159.2014.915746. Epub 2014 May 16. Review. PubMed PMID: 24834478.
9: Dieci E, Casati L, Pagani F, Celotti F, Sibilia V. Acylated and unacylated ghrelin protect MC3T3-E1 cells against tert-butyl hydroperoxide-induced oxidative injury: pharmacological characterization of ghrelin receptor and possible epigenetic involvement. Amino Acids. 2014 Jul;46(7):1715-25. doi: 10.1007/s00726-014-1734-y. Epub 2014 Apr 5. PubMed PMID: 24705647.
10: Lucchi C, Curia G, Vinet J, Gualtieri F, Bresciani E, Locatelli V, Torsello A, Biagini G. Protective but not anticonvulsant effects of ghrelin and JMV-1843 in the pilocarpine model of Status epilepticus. PLoS One. 2013 Aug 28;8(8):e72716. doi: 10.1371/journal.pone.0072716. eCollection 2013. PubMed PMID: 24015271; PubMed Central PMCID: PMC3755992.
11: Holubová M, Spolcová A, Demianová Z, Sýkora D, Fehrentz JA, Martinez J, Stofková A, Jurčovičová J, Drápalová J, Lacinová Z, Haluzík M, Zelezná B, Maletínská L. Ghrelin agonist JMV 1843 increases food intake, body weight and expression of orexigenic neuropeptides in mice. Physiol Res. 2013;62(4):435-44. Epub 2013 Apr 16. PubMed PMID: 23590608.
12: Garcia JM, Swerdloff R, Wang C, Kyle M, Kipnes M, Biller BM, Cook D, Yuen KC, Bonert V, Dobs A, Molitch ME, Merriam GR. Macimorelin (AEZS-130)-stimulated growth hormone (GH) test: validation of a novel oral stimulation test for the diagnosis of adult GH deficiency. J Clin Endocrinol Metab. 2013 Jun;98(6):2422-9. doi: 10.1210/jc.2013-1157. Epub 2013 Apr 4. PubMed PMID: 23559086; PubMed Central PMCID: PMC4207947.
13: Sibilia V, Pagani F, Mrak E, Dieci E, Tulipano G, Ferrucci F. Pharmacological characterization of the ghrelin receptor mediating its inhibitory action on inflammatory pain in rats. Amino Acids. 2012 Oct;43(4):1751-9. Epub 2012 Mar 10. PubMed PMID: 22407485; PubMed Central PMCID: PMC3448055.
14: Osterstock G, Escobar P, Mitutsova V, Gouty-Colomer LA, Fontanaud P, Molino F, Fehrentz JA, Carmignac D, Martinez J, Guerineau NC, Robinson IC, Mollard P, Méry PF. Ghrelin stimulation of growth hormone-releasing hormone neurons is direct in the arcuate nucleus. PLoS One. 2010 Feb 11;5(2):e9159. doi: 10.1371/journal.pone.0009159. PubMed PMID: 20161791; PubMed Central PMCID: PMC2820089.
15: MacLean CM, Casanova AT, Baselgia-Jeker L, Neave N, Larsen F, Skillern L, Drewe J, Beglinger C. Effect of food on the pharmacokinetics and pharmacodynamics of an oral ghrelin agonist (ARD-07) in healthy subjects. J Clin Pharmacol. 2009 May;49(5):553-9. doi: 10.1177/0091270008330160. Epub 2009 Mar 17. PubMed PMID: 19293342.
16: Piccoli F, Degen L, MacLean C, Peter S, Baselgia L, Larsen F, Beglinger C, Drewe J. Pharmacokinetics and pharmacodynamic effects of an oral ghrelin agonist in healthy subjects. J Clin Endocrinol Metab. 2007 May;92(5):1814-20. Epub 2007 Feb 6. Erratum in: J Clin Endocrinol Metab. 2008 Mar;93(3):1082. PubMed PMID: 17284637.
17: Deghenghi R, Broglio F, Papotti M, Muccioli G, Ghigo E. Targeting the ghrelin receptor: orally active GHS and cortistatin analogs. Endocrine. 2003 Oct;22(1):13-8. Review. PubMed PMID: 14610294.
18: Guerlavais V, Boeglin D, Mousseaux D, Oiry C, Heitz A, Deghenghi R, Locatelli V, Torsello A, Ghé C, Catapano F, Muccioli G, Galleyrand JC, Fehrentz JA, Martinez J. New active series of growth hormone secretagogues. J Med Chem. 2003 Mar 27;46(7):1191-203. PubMed PMID: 12646029.
19: Broglio F, Boutignon F, Benso A, Gottero C, Prodam F, Arvat E, Ghè C, Catapano F, Torsello A, Locatelli V, Muccioli G, Boeglin D, Guerlavais V, Fehrentz JA, Martinez J, Ghigo E, Deghenghi R. EP1572: a novel peptido-mimetic GH secretagogue with potent and selective GH-releasing activity in man. J Endocrinol Invest. 2002 Sep;25(8):RC26-8. PubMed PMID: 12240910.