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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
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
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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
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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