IBUTAMOREN MESYLATE

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 Search

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
Sources: http://adisinsight.springer.com/drugs/800007434
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Somatotropin 2 Target ID: P01241 Gene ID: 2688.0 Gene Symbol: GH1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7624358 \| https://www.ncbi.nlm.nih.gov/pubmed/9329386	Releasing Agent 8	1.3 nM [EC50]
Ghrelin receptor 15 Target ID: CHEMBL4616 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18923064 \| https://www.ncbi.nlm.nih.gov/pubmed/11314756 \| https://www.ncbi.nlm.nih.gov/pubmed/15905359 \| https://www.ncbi.nlm.nih.gov/pubmed/9092793 \| https://www.ncbi.nlm.nih.gov/pubmed/8838145	Agonist 2678	0.3 nM [EC50]
Insulin-like growth factor I 3 Target ID: CHEMBL3217394 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9329386	Releasing Agent 8

Conditions

Condition	Modality	Highest Phase	Product
Fibromyalgia 89 Sources: http://adisinsight.springer.com/drugs/800007434	Primary	Phase II 1132	Unknown Approved Use Unknown
Hip fracture 2 Sources: http://adisinsight.springer.com/drugs/800007434	Primary	Phase II 1132	Unknown Approved Use Unknown
Chronic kidney disease 56 Sources: http://adisinsight.springer.com/drugs/800007434	Primary	Phase II 1132	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: http://adisinsight.springer.com/drugs/800007434	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P001RUC	https://www.1pchem.com/search?query=1P001RUC
AK Scientific	3727AH	https://aksci.com/item_detail.php?cat=3727AH
ApexBio Technology	A3481	https://www.apexbt.com/catalogsearch/result/?q=A3481
AstaTech	40802	http://astatechinc.com/CPSResult.php?CRNO=40802
AstaTech	43760	http://astatechinc.com/CPSResult.php?CRNO=43760
Axon MedChem	1376	https://www.axonmedchem.com/product/1376
BLD Pharm	BD558977	http://www.bldpharm.com/search/Search.html?keyword=BD558977
BOC Sciences	159634-47-6	http://www.bocsci.com/description.asp?cas=159634-47-6
BOC Sciences	159752-10-0	http://www.bocsci.com/description.asp?cas=159752-10-0
Cayman Chemical	18003	http://www.caymanchem.com/app/template/Product.vm/catalog/18003
Chem Scene	CS-0444	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0444
ChemShuttle	104910	https://www.chemshuttle.com/catalogsearch/result/?q=104910
KeyOrganics	ES-0005	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=ES-0005
Matrix Scientific	145256	http://www.matrixscientific.com/145256.html
MedChem Express	HY-50844	https://www.medchemexpress.com/search.html?q=HY-50844&ft=&fa=&fp=
MolPort	MolPort-020-313-394	https://www.molport.com/shop/molecule-link/MolPort-020-313-394
Molcore	MC445645	http://www.molcore.com/CatMC445645.html
Molnova	M12288	https://www.molnova.com/en/serch-list.html?keywords=M12288
MuseChem	I002024	https://www.musechem.com/product/I002024.html
MuseChem	M039670	https://www.musechem.com/product/M039670.html
TargetMol	T7112	https://www.targetmol.com/search?keyword=T7112
Tocris	5272	https://www.tocris.com/search.php?Type=QuickSearch&Value=5272
eMolecules	110048211	https://orderbb.emolecules.com/search/#?query=110048211
eMolecules	192772168	https://orderbb.emolecules.com/search/#?query=192772168
eMolecules	275034694	https://orderbb.emolecules.com/search/#?query=275034694
eMolecules	300546003	https://orderbb.emolecules.com/search/#?query=300546003
eMolecules	36367042	https://orderbb.emolecules.com/search/#?query=36367042
mcule	MCULE-4037288380	https://mcule.com/MCULE-4037288380/
mcule	MCULE-4179707697	https://mcule.com/MCULE-4179707697/
mcule	MCULE-5004202874	https://mcule.com/MCULE-5004202874/
mcule	MCULE-8989219658	https://mcule.com/MCULE-8989219658/

PubMed

Title	Date	PubMed
Design and biological activities of L-163,191 (MK-0677): a potent, orally active growth hormone secretagogue.	1995 Jul 18	7624358
Identification of a new G-protein-linked receptor for growth hormone secretagogues.	1996 Jan	8838145
Molecular analysis of rat pituitary and hypothalamic growth hormone secretagogue receptors.	1997 Apr	9092793
Pharmacological characterisation of a new oral GH secretagogue, NN703.	1999 Aug	10427162
Binding of 125I-labeled ghrelin to membranes from human hypothalamus and pituitary gland.	2001 Mar	11314756
Nonpeptide and peptide growth hormone secretagogues act both as ghrelin receptor agonist and as positive or negative allosteric modulators of ghrelin signaling.	2005 Sep	15905359

Patents

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.

Name

Type

Language

IBUTAMOREN MESYLATE

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