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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H36N4O5S
Molecular Weight 528.664
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBUTAMOREN

SMILES

CC(C)(N)C(=O)N[C@H](COCC1=CC=CC=C1)C(=O)N2CCC3(CN(C4=C3C=CC=C4)S(C)(=O)=O)CC2

InChI

InChIKey=UMUPQWIGCOZEOY-JOCHJYFZSA-N
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

HIDE SMILES / InChI

Molecular Formula C27H36N4O5S
Molecular Weight 528.664
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ibutamoren (L-163,191 MK-0677) is a spiropiperidine agonist of the ghrelin receptor and a growth hormone secretagogue. Ibutamoren mimics the actions of growth hormone releasing peptide-6 to increase serum levels of serum insulin-like growth factor-I (IGF-I). Orally active Ibutamoren was being developed by Merck & Co. for a variety of indications, including fibromyalgia, muscle wasting/weakness in patients with chronic kidney disease, Alzheimer's disease and fractures.However, there has been no recent development reported or development has been discontinued for these indications.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.3 nM [EC50]
0.3 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
25 mg once daily: over 12 months, the ghrelin mimetic Ibutamoren (L-163,191 MK-0677) enhanced pulsatile growth hormone secretion, significantly increased fat-free mass, and was generally well tolerated. Long-term functional and, ultimately, pharmacoeconomic, studies in elderly persons are indicated.
Route of Administration: Oral
In Vitro Use Guide
1 uM MK-0677 inhibits cell death and activate ERK1/2 and Akt in H9c2 cardiomyocytes and PAE.
Substance Class Chemical
Record UNII
GJ0EGN38UL
Record Status Validated (UNII)
Record Version