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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=CC=CC=C34)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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18923064 | https://www.ncbi.nlm.nih.gov/pubmed/7624358 | https://www.ncbi.nlm.nih.gov/pubmed/9329386

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.

Originator

Curator's Comment: # Merck & Co

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Design and biological activities of L-163,191 (MK-0677): a potent, orally active growth hormone secretagogue.
1995 Jul 18
Identification of a new G-protein-linked receptor for growth hormone secretagogues.
1996 Jan
Molecular analysis of rat pituitary and hypothalamic growth hormone secretagogue receptors.
1997 Apr
Pharmacological characterisation of a new oral GH secretagogue, NN703.
1999 Aug
Binding of 125I-labeled ghrelin to membranes from human hypothalamus and pituitary gland.
2001 Mar
Nonpeptide and peptide growth hormone secretagogues act both as ghrelin receptor agonist and as positive or negative allosteric modulators of ghrelin signaling.
2005 Sep
Patents

Sample Use Guides

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
1 uM MK-0677 inhibits cell death and activate ERK1/2 and Akt in H9c2 cardiomyocytes and PAE.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:37:02 GMT 2025
Edited
by admin
on Mon Mar 31 18:37:02 GMT 2025
Record UNII
GJ0EGN38UL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
L-163,191
Preferred Name English
IBUTAMOREN
INN  
INN  
Official Name English
2-AMINO-N-(3-(BENZYLOXY)-1-(1-METHANESULFONYL-1,2-DIHYDROSPIRO(INDOLE-3,4'-PIPERIDIN)-1'-YL)-1-OXOPROPAN-2-YL)-2-METHYLPROPANAMIDE
Systematic Name English
Ibutamoren [WHO-DD]
Common Name English
ibutamoren [INN]
Common Name English
2-AMINO-N-((R)-2-(BENZYLOXY)-1-((1-(METHYLSULFONYL)SPIRO(INDOLINE-3,4'-PIPERIDIN)-1'-YL)CARBONYL)ETHYL)-2-METHYLPROPIONAMIDE
Systematic Name English
IBUTAMOREN [NFLIS-DRUG]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1910
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
WIKIPEDIA Designer-drugs-Ibutamoren
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
DSLD 3997 (Number of products:8)
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
Code System Code Type Description
WIKIPEDIA
IBUTAMOREN
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
PUBCHEM
178024
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
INN
7682
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
NCI_THESAURUS
C97488
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
EVMPD
SUB08100MIG
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
DAILYMED
GJ0EGN38UL
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
SMS_ID
100000083649
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
ChEMBL
CHEMBL13817
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
CAS
159634-47-6
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
FDA UNII
GJ0EGN38UL
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
RXCUI
1805438
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID90166700
Created by admin on Mon Mar 31 18:37:02 GMT 2025 , Edited by admin on Mon Mar 31 18:37:02 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY