Ibutamoren information

Ibutamoren
Clinical data
Other names	MK-677; MK-0677; L-163,191; Oratrope
Routes of; administration	By mouth
Legal status
Legal status	Investigational New Drug;
Pharmacokinetic data
Elimination half-life	4–6 hours (in beagles); IGF-1 levels remain elevated in humans with a single oral dose for up to 24 hours
Identifiers
	IUPAC name 2-amino-2-methyl-N-[1-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl]propanamide;
CAS Number	159634-47-6 ; 159752-10-0 (mesylate);
PubChem CID	9939050;
ChemSpider	154975;
UNII	GJ0EGN38UL;
CompTox Dashboard (EPA)	DTXSID90166700 ;
ECHA InfoCard	100.236.734
Chemical and physical data
Formula	C27H36N4O5S
Molar mass	528.67 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(C)(=O)N(C2)c1ccccc1C23CCN(CC3)C(=O)C(NC(=O)C(N)(C)C)COCc4ccccc4;
	InChI InChI=1S/C27H36N4O5S/c1-26(2,28)25(33)29-22(18-36-17-20-9-5-4-6-10-20)24(32)30-15-13-27(14-16-30)19-31(37(3,34)35)23-12-8-7-11-21(23)27/h4-12,22H,13-19,28H2,1-3H3,(H,29,33)/t22-/m1/s1; Key:UMUPQWIGCOZEOY-JOCHJYFZSA-N;
	(verify)

Ibutamoren (INNTooltip International Nonproprietary Name) (developmental code names MK-677, MK-0677, LUM-201, L-163,191; former tentative brand name Oratrope) is a potent, long-acting, orally-active, selective, and non-peptide agonist of the ghrelin receptor and a growth hormone secretagogue, mimicking the growth hormone (GH)-stimulating action of the endogenous hormone ghrelin.^[3]^[4]^[5]^[6]^[7] It has been shown to increase the secretion of several hormones including GH and insulin-like growth factor 1 (IGF-1) and produces sustained increases in the plasma levels of these hormones without affecting cortisol levels.^[8]

^ Smith RG, Thorner MO (28 January 2000). Human Growth Hormone: Research and Clinical Practice. Springer Science & Business Media. pp. 45–. ISBN 978-1-59259-015-5.
^ Smith RG, Van der Ploeg LH, Howard AD, Feighner SD, Cheng K, Hickey GJ, et al. (October 1997). "Peptidomimetic regulation of growth hormone secretion". Endocrine Reviews. 18 (5). The Endocrine Society: 621–645. doi:10.1210/edrv.18.5.0316. PMID 9331545.
^ "Ibutamoren - Lumos Pharma/Merck". AdisInsight.
^ Patchett AA, Nargund RP, Tata JR, Chen MH, Barakat KJ, Johnston DB, et al. (July 1995). "Design and biological activities of L-163,191 (MK-0677): a potent, orally active growth hormone secretagogue". Proceedings of the National Academy of Sciences of the United States of America. 92 (15): 7001–7005. Bibcode:1995PNAS...92.7001P. doi:10.1073/pnas.92.15.7001. PMC 41459. PMID 7624358.
^ Pong SS, Chaung LY, Dean DC, Nargund RP, Patchett AA, Smith RG (January 1996). "Identification of a new G-protein-linked receptor for growth hormone secretagogues". Molecular Endocrinology. 10 (1): 57–61. doi:10.1210/mend.10.1.8838145. PMID 8838145.
^ Cassoni P, Papotti M, Ghè C, Catapano F, Sapino A, Graziani A, et al. (April 2001). "Identification, characterization, and biological activity of specific receptors for natural (ghrelin) and synthetic growth hormone secretagogues and analogs in human breast carcinomas and cell lines". The Journal of Clinical Endocrinology and Metabolism. 86 (4): 1738–1745. doi:10.1210/jcem.86.4.7402. PMID 11297611.
^ Holst B, Frimurer TM, Mokrosinski J, Halkjaer T, Cullberg KB, Underwood CR, Schwartz TW (January 2009). "Overlapping binding site for the endogenous agonist, small-molecule agonists, and ago-allosteric modulators on the ghrelin receptor". Molecular Pharmacology. 75 (1): 44–59. doi:10.1124/mol.108.049189. PMID 18923064. S2CID 2218638.
^ Copinschi G, Van Onderbergen A, L'Hermite-Balériaux M, Mendel CM, Caufriez A, Leproult R, et al. (August 1996). "Effects of a 7-day treatment with a novel, orally active, growth hormone (GH) secretagogue, MK-677, on 24-hour GH profiles, insulin-like growth factor I, and adrenocortical function in normal young men". The Journal of Clinical Endocrinology and Metabolism. 81 (8): 2776–2782. doi:10.1210/jcem.81.8.8768828. PMID 8768828.

[SmithThorner2000-1] Smith RG, Thorner MO (28 January 2000). Human Growth Hormone: Research and Clinical Practice. Springer Science & Business Media. pp. 45–. ISBN 978-1-59259-015-5.

[Smith_Ploeg_Howard_Feighner_1997_pp._621–645-2] Smith RG, Van der Ploeg LH, Howard AD, Feighner SD, Cheng K, Hickey GJ, et al. (October 1997). "Peptidomimetic regulation of growth hormone secretion". Endocrine Reviews. 18 (5). The Endocrine Society: 621–645. doi:10.1210/edrv.18.5.0316. PMID 9331545.

[AdisInsight-3] "Ibutamoren - Lumos Pharma/Merck". AdisInsight.

[:0-4] Patchett AA, Nargund RP, Tata JR, Chen MH, Barakat KJ, Johnston DB, et al. (July 1995). "Design and biological activities of L-163,191 (MK-0677): a potent, orally active growth hormone secretagogue". Proceedings of the National Academy of Sciences of the United States of America. 92 (15): 7001–7005. Bibcode:1995PNAS...92.7001P. doi:10.1073/pnas.92.15.7001. PMC 41459. PMID 7624358.

[:1-5] Pong SS, Chaung LY, Dean DC, Nargund RP, Patchett AA, Smith RG (January 1996). "Identification of a new G-protein-linked receptor for growth hormone secretagogues". Molecular Endocrinology. 10 (1): 57–61. doi:10.1210/mend.10.1.8838145. PMID 8838145.

[:2-6] Cassoni P, Papotti M, Ghè C, Catapano F, Sapino A, Graziani A, et al. (April 2001). "Identification, characterization, and biological activity of specific receptors for natural (ghrelin) and synthetic growth hormone secretagogues and analogs in human breast carcinomas and cell lines". The Journal of Clinical Endocrinology and Metabolism. 86 (4): 1738–1745. doi:10.1210/jcem.86.4.7402. PMID 11297611.

[:3-7] Holst B, Frimurer TM, Mokrosinski J, Halkjaer T, Cullberg KB, Underwood CR, Schwartz TW (January 2009). "Overlapping binding site for the endogenous agonist, small-molecule agonists, and ago-allosteric modulators on the ghrelin receptor". Molecular Pharmacology. 75 (1): 44–59. doi:10.1124/mol.108.049189. PMID 18923064. S2CID 2218638.

[8] Copinschi G, Van Onderbergen A, L'Hermite-Balériaux M, Mendel CM, Caufriez A, Leproult R, et al. (August 1996). "Effects of a 7-day treatment with a novel, orally active, growth hormone (GH) secretagogue, MK-677, on 24-hour GH profiles, insulin-like growth factor I, and adrenocortical function in normal young men". The Journal of Clinical Endocrinology and Metabolism. 81 (8): 2776–2782. doi:10.1210/jcem.81.8.8768828. PMID 8768828.

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Clinical data

Other names	MK-677; MK-0677; L-163,191; Oratrope
Routes of administration	By mouth
Legal status
Legal status	Investigational New Drug
Pharmacokinetic data
Elimination half-life	4–6 hours (in beagles);^[1] IGF-1 levels remain elevated in humans with a single oral dose for up to 24 hours^[2]
Identifiers
IUPAC name 2-amino-2-methyl-N-[1-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl]propanamide
CAS Number	159634-47-6^Y 159752-10-0 (mesylate)
PubChem CID	9939050
ChemSpider	154975
UNII	GJ0EGN38UL
CompTox Dashboard (EPA)	DTXSID90166700
ECHA InfoCard	100.236.734
Chemical and physical data
Formula	C₂₇H₃₆N₄O₅S
Molar mass	528.67 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=S(C)(=O)N(C2)c1ccccc1C23CCN(CC3)C(=O)C(NC(=O)C(N)(C)C)COCc4ccccc4
InChI InChI=1S/C27H36N4O5S/c1-26(2,28)25(33)29-22(18-36-17-20-9-5-4-6-10-20)24(32)30-15-13-27(14-16-30)19-31(37(3,34)35)23-12-8-7-11-21(23)27/h4-12,22H,13-19,28H2,1-3H3,(H,29,33)/t22-/m1/s1 Key:UMUPQWIGCOZEOY-JOCHJYFZSA-N
(verify)