MITOGLITAZONE

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H18N2O4S
Molecular Weight	370.422
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=CN=C(C=C1)C(=O)COC2=CC=C(CC3SC(=O)NC3=O)C=C2

InChI

InChIKey=IRNJSRAGRIZIHD-UHFFFAOYSA-N

InChI=1S/C19H18N2O4S/c1-2-12-5-8-15(20-10-12)16(22)11-25-14-6-3-13(4-7-14)9-17-18(23)21-19(24)26-17/h3-8,10,17H,2,9,11H2,1H3,(H,21,23,24)

HIDE SMILES / InChI

Molecular Formula	C19H18N2O4S
Molecular Weight	370.422
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23563205 | http://www.msdrx.com/pipeline/msdc-0160 | https://www.ncbi.nlm.nih.gov/pubmed/27928028

Mitoglitazone (previously known as MSDC-0160 or CAY-10415) is a mTOT (mitochondrial target of thiazolidinediones) modulator that targets the mitochondrial pyruvate carrier (MPC), which is a key controller of cellular metabolism. MSDC-0160 is modulated MPC and act as insulin sensitizers without activating PPAR gamma. (Mitoglitazone exhibits very low binding affinity and activity at PPARγ). Mitoglitazone has been used in trials phase II studying the treatment of Type 2 Diabetes and Alzheimer's disease; the treatment for diabetes was discontinued. In addition, MSDC-0160 has demonstrated significant neuroprotective effects in the En1+/- mouse model of Parkinson’s disease via modulation of the mTOR-autophagy signaling cascade.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mitochondrial pyruvate carrier 1 1 Target ID: Q9Y5U8 Gene ID: 51660.0 Gene Symbol: MPC1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27928028	Modulator 828
Mitochondrial pyruvate carrier 2 1 Target ID: O95563 Gene ID: 25874.0 Gene Symbol: MPC2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27928028	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: http://www.msdrx.com/pipeline/msdc-0160	Primary	Phase II 1132	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: http://www.msdrx.com/pipeline/msdc-0160	Primary	Basic research	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: http://www.msdrx.com/pipeline/msdc-0160	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY106888	https://www.001chemical.com/chem/146062-49-9
AA Blocks	AA001DK7	https://www.aablocks.com/goods/Goods/detail?id=AA001DK7
AK Scientific, Inc. (AKSCI)	2172AH	http://www.aksci.com/item_detail.php?cat=2172AH
Aaron Chemicals	AR001EBZ	http://www.aaronchem.com/146062-49-9
AbMole Bioscience	M2870	http://www.abmole.com/products/msdc-0160.html
Acadechem	ACDS-0781754	http://acadechemical.com/product/229301
Achemtek	0102-028722	http://www.achemtek.com/146062-49-9
Alfa Chemistry	AP146062499	https://reagents.alfa-chemistry.com/product/mitoglitazone-cas-146062-49-9-5131.html
Ambeed	A318812	https://www.ambeed.com/products/146062-49-9.html
Ambinter	Amb24123254	http://www.ambinter.com/reference/24123254
Angene	AGN-PC-0WH9A0	http://www.angenechemical.com/productshow/AGN-PC-0WH9A0.html
Ark Pharm	AK471596	http://www.arkpharminc.com/products/146062-49-9.html
Ark Pharma Scientific Limited	H-015431	http://www.arkpharmtech.com/product/20486.html
Ark Pharma Scientific Limited	A-1986	http://www.arkpharmtech.com/product/274556.html
Aurora Fine Chemicals LLC	K16.609.480	http://online.aurorafinechemicals.com/info?ID=K16.609.480
BLD Pharm	BD556700	http://www.bldpharm.com/products/146062-49-9.html
BOC Sciences	146062-49-9	https://www.bocsci.com/msdc-0160-cas-146062-49-9-item-84-311834.html
BioChemPartner	BCP16099	http://www.biochempartner.com/146062-49-9-BCP16099
BioCrick	BCC5343	http://www.biocrick.com/MSDC-0160-BCC5343.html
BioSynth	J-008189	https://www.biosynth.com/en/products/all-products/products/J-008189.html
CSNpharm	CSN17115	https://www.csnpharm.com/products/msdc-0160.html
Chem Scene	CS-6405	http://www.chemscene.com/146062-49-9.html
ChemShuttle	108255	http://www.chemshuttle.com/catalogsearch/result/?q=146062-49-9&cat=
Chemspace	CSSB00015189817	https://chem-space.com/CSSB00015189817
DC Chemicals	DC8482	http://www.dcchemicals.com/product_show-CAY10415.html
Excenen	EX-A1483	http://www.excenen.com/searchresultlist.php?id=146062-49-9
Lab Network	LN01323874	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01323874
Matrix Scientific	132281	https://www.matrixscientific.com/132281.html
MedChem Express	HY-100550	https://www.medchemexpress.com/MSDC_0160.html
MolPort	MolPort-009-018-762	https://www.molport.com/shop/molecule-link/MolPort-009-018-762
Molcore	MC106888	https://www.molcore.com/product/146062-49-9
MuseChem	I005690	https://www.musechem.com/product/I005690.html
Selleck Chemicals	S7453	http://www.selleckchem.com/products/msdc-0160.html
Sigma-Aldrich	SML1884_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/sml1884?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S522799	http://www.smolecule.com/products/s522799
Sun-shine Chemical	CAY10415	http://www.sun-shinechem.com/Details/CAY10415/2032/146062-49-9.html
Synblock Inc	SB17325	http://www.synblock.com/product/146062-49-9.html
THE BioTek	bt-263058	https://www.thebiotek.com/product/inhibitors/bt-263058
Tocris	5799	https://www.tocris.com/products/mitoglitazone_5799
abcr GmbH	AB492568	http://www.abcr.com/shop/en/AB492568
eNovation Chemicals	D491758	https://www.enovationchem.com/ProductDetails.asp?ProductID=D491758
eNovation Chemicals	D513571	https://www.enovationchem.com/ProductDetails.asp?ProductID=D513571
eNovation Chemicals	Y0991320	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0991320

PubMed

Title	Date	PubMed
An evaluation of MSDC-0160, a prototype mTOT modulating insulin sensitizer, in patients with mild Alzheimer's disease.	2014	24931567

Patents

Sample Use Guides

In Vivo Use Guide

150 mg capsules given once daily for 90 days

Route of Administration: Oral

In Vitro Use Guide

Treatment of Human Islets with MSDC-0160 (MITOGLITAZONE) activates AMPK and downregulates mTOR. Human islets were cultured with 5 mM glucose and MSDC-0160 (1–50 µM) for 24 h. Phosphorylation of mTOR was significantly decreased at 20 and 50 µM MSDC-0160. This inhibition inversely correlated with increased phosphorylation of AMPK and its downstream target acetyl CoA carboxylase (ACC). Consistent with the reduction in the amount of phosphorylated mTOR, treatment with MSDC-0160 also produced a decrease in the phosphorylation of S6, a downstream indicator of the mTOR pathway. This was evident after 4 days of culture under these conditions, but occurred as early as 90 minutes into the treatment. Taken together, these data suggest that MSDC-0160 restores the insulin signaling pathway at least in part by modulating mTOR activity.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:00:51 GMT 2023` Edited by `admin` on `Sat Dec 16 11:00:51 GMT 2023`
Record UNII	29I7RP18RG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MITOGLITAZONE

Common Name

English

5-(4-(2-(5-ETHYL-2-PYRIDINYL)-2-OXOETHOXY)BENZYL)THIAZOLIDINE-2,4-DIONE

Systematic Name

English

2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-ETHYL-2-PYRIDINYL)-2-OXOETHOXY)PHENYL)METHYL)-

Systematic Name

English

CAY-10415

Code

English

MSD-9

Code

English

U-91325

Code

English

MSDC-0160

Code

English

J730.386F

Code

English

PNU-91325

Code

English

Code System Code Type Description

CAS

146062-49-9