U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H36N4O5S.CH4O3S
Molecular Weight 624.769
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBUTAMOREN MESYLATE

SMILES

CS(O)(=O)=O.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=DUGMCDWNXXFHDE-VZYDHVRKSA-N
InChI=1S/C27H36N4O5S.CH4O3S/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;1-5(2,3)4/h4-12,22H,13-19,28H2,1-3H3,(H,29,33);1H3,(H,2,3,4)/t22-;/m1./s1

HIDE SMILES / InChI

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
Pharmacological characterisation of a new oral GH secretagogue, NN703.
1999 Aug
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.
Name Type Language
IBUTAMOREN MESYLATE
USAN  
USAN  
Official Name English
2-AMINO-N-((R)-2-(BENZYLOXY)-1-((1-(METHYLSULFONYL)SPIRO(INDOLINE-3,4'-PIPERIDIN)-1'-YL)CARBONYL)ETHYL)-2-METHYLPROPIONAMIDE MONOMETHANESULFONATE
Systematic Name English
MK-0677
Code English
2-AMINO-N-(2-(1,2-DIHYDRO-1-(METHYLSULFONYL)SPIRO(3H-INDOLE-3,4'-PIPERIDIN)-1'-YL)-2-OXO-1-((PHENYLMETHOXY)METHYL)ETHYL)-2-METHYLPROPANAMIDE MESYLATE -L
Common Name English
2-AMINO-N-((R)-2-(BENZYLOXY)-1-((1-(METHYLSULPHONYL)SPIRO(INDOLINE-3,4'-PIPERIDIN)-1'-YL)CARBONYL)ETHYL)-2-METHYLPROPIONAMIDE MONOMETHANESULPHONATE
Systematic Name English
2-AMINO-N-(2-(1,2-DIHYDRO-1-(METHYLSULFONYL)SPIRO(3H-INDOLE-3,4'-PIPERIDIN)-1'-YL)-2-OXO-1-((PHENYLMETHOXY)METHYL)ETHYL)-2-METHYLPROPANAMIDE MESILATE -L
Common Name English
IBUTAMOREN MESYLATE [USAN]
Common Name English
IBUTAMOREN MESILATE
Common Name English
MK-677
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 579617
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
DSLD 4043 (Number of products:1)
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
NCI_THESAURUS C1910
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
EU-Orphan Drug EU/3/17/1882
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
Code System Code Type Description
MESH
C094817
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
RXCUI
1805437
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
CAS
159752-10-0
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL13817
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
FDA UNII
R90JB6QJ2B
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
PUBCHEM
6450830
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
NCI_THESAURUS
C97489
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
SMS_ID
100000175137
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
USAN
II-74
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID50936168
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
DAILYMED
R90JB6QJ2B
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY