Basic information
- CAS
159634-47-6- Standard SMILES
CC(C)(N)C(=O)N[C@H](COCc1ccccc1)C(=O)N1CCC2(CC1)CN(S(C)(=O)=O)c1ccccc12- InChIKey
UMUPQWIGCOZEOY-JOCHJYFZSA-N- Molecular formula
- C27H36N4O5S
- Average molar mass
- 528.7 g/mol
- Monoisotopic mass
- 528.24064144
Overview
Ibutamoren is an orally bioavailable, small molecule, non-peptide growth hormone secretagogue (GHS). Upon administration, ibutamoren promotes the release of growth hormone (GH) from the pituitary gland, thereby increasing plasma GH levels. This may counteract GH deficiency. GH plays an important role in many biological processes.
Names & identifiers
- Preferred name
- Ibutamoren
- IUPAC
- 2-amino-2-methyl-N-[(2R)-1-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl]propanamide
- English name
- MK-677
- Molecular formula
- C27H36N4O5S
- Molecular weight
- 528.66
Names & synonyms
Ibutamoren159634-47-6ibutamorenoGJ0EGN38ULL 1631912-amino-2-methyl-N-[(2R)-1-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl]propanamideL-163,191DTXSID901667002-AMINO-N-((R)-2-(BENZYLOXY)-1-((1-(METHYLSULFONYL)SPIRO(INDOLINE-3,4'-PIPERIDIN)-1'-YL)CARBONYL)ETHYL)-2-METHYLPROPIONAMIDE2-AMINO-N-(3-(BENZYLOXY)-1-(1-METHANESULFONYL-1,2-DIHYDROSPIRO(INDOLE-3,4'-PIPERIDIN)-1'-YL)-1-OXOPROPAN-2-YL)-2-METHYLPROPANAMIDEibutamorenum2-amino-2-methyl-N-((2R)-1-(1-methylsulfonylspiro(2H-indole-3,4'-piperidine)-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl)propanamide
Show more names
IbutaMoren (MK-677)MK-677Mk677 SarmsMK-0677MK-677Ibutamoren, 10 mM in DMSOIBUTAMOREN (MK-677), CID178024MK-677?/?Ibutamoren 10mg TabletsIbutamoren,MK-677, MK-0677, L-163,191Ibutamoren mesylate (MK-0667, L163191)
RefChem:55388DTXCID0089191Ibutamoren [INN]CHEMBL13817(R)-2-amino-N-(3-(benzyloxy)-1-(1-(methylsulfonyl)spiro[indoline-3,4'-piperidin]-1'-yl)-1-oxopropan-2-yl)-2-methylpropanamide192511-65-2MK-677, (HCl salt)CHEMBL542653
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 130 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 8
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 920
Experimental & physicochemical properties
LogP2.37
Physicochemical properties
- Density
- 1.32 · 1.32
- pka
- 15.73 · 15.73±0.46(Predicted)
- form
- Solid
- color
- White to off-white
- InChIKey
- UMUPQWIGCOZEOY-JOCHJYFZSA-N
- SMILES
- C(N[C@H](COCC1=CC=CC=C1)C(N1CCC2(CC1)C1=C(N(S(C)(=O)=O)C2)C=CC=C1)=O)(=O)C(N)(C)C
- FDA UNII
- 0 EGN38UL · GJ0EGN38UL
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Applications
DescriptionIbutamoren (INN) (developmental code names MK-677, MK-0677, L-163,191)is a non-peptidic, potent, long acting, orally-active, and selective agonist of the ghrelin receptor and a growth hormone secretagogue, mimicking the growth hormone (GH)-stimulating action of the endogenous hormone ghrelin. It has been demonstrated to increase the release of, and produces sustained increases in plasma levels of several hormones including GH and insulin-like growth factor 1 (IGF-1), but without affecting cortisol levels. MK677 has shown to sustain activation of GH-IGF-1 Axis and increase in lean body mass but no change in total fat mass or visceral fat. It is currently under development as a potential treatment for reduced levels of these hormones, such as in children or elderly adults with growth hormone deficiency, and human studies have shown it to increase both muscle mass and bone mineral density, making it a promising therapy for the treatment of frailty in the elderly.
UsesGrowth hormone releasing factor.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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