MEGLUTOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10O5
Molecular Weight	162.1406
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)(CC(O)=O)CC(O)=O

InChI

InChIKey=NPOAOTPXWNWTSH-UHFFFAOYSA-N

InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68015093 | https://www.ncbi.nlm.nih.gov/pubmed/6180274

Meglutol (3-Hydroxy-3-methylglutaric acid, HMGA) is an antilipemic agent which lowers cholesterol, triglycerides, serum beta-lipoproteins and phospholipids, and inhibits the activity of hydroxymethylglutarryl CoA reductases, which is the rate-limiting enzyme in the biosynthesis of cholesterol. 3-Hydroxy-3-methylglutaric acid (HMGA) is a competitive inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase (HMGCoAR) and strongly reduces cholesterol biosynthesis both in vitro and in vivo. In hamster model HMGA is effective in reducing both bile cholesterol supersaturation and hypercholesterolemia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
HMG-CoA reductase 47 Target ID: CHEMBL402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15686898	Inhibitor 8297		4.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypercholesterolemia 47 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6180274	Primary		Approved 8429	Lipoglutaren Approved Use Hypolipidemic

PubMed

Title	Date	PubMed
3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria.	1976 Aug 2	947633
Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.	1994 Jun	8087979
Mitochondrial DNA depletion associated with partial complex II and IV deficiencies and 3-methylglutaconic aciduria.	2001 Feb	11292221
Biochemical and molecular analyses in three patients with 3-hydroxy-3-methylglutaric aciduria.	2003	14518825
Structural (betaalpha)8 TIM barrel model of 3-hydroxy-3-methylglutaryl-coenzyme A lyase.	2003 Aug 1	12746442
Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats.	2004 Jul	15231000
Evidence that 3-hydroxy-3-methylglutaric acid promotes lipid and protein oxidative damage and reduces the nonenzymatic antioxidant defenses in rat cerebral cortex.	2008 Feb 15	17941049
Anti-microtubule activity of tubeimoside I and its colchicine binding site of tubulin.	2008 Sep	18030471
The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides.	2009 Jan	19155025
Striatum is more vulnerable to oxidative damage induced by the metabolites accumulating in 3-hydroxy-3-methylglutaryl-CoA lyase deficiency as compared to liver.	2009 Jun	19460629
Ten novel HMGCL mutations in 24 patients of different origin with 3-hydroxy-3-methyl-glutaric aciduria.	2009 Mar	19177531
Metabolic profiling reveals local and systemic responses of host plants to nematode parasitism.	2010 Jun 1	20374527

Patents

Sample Use Guides

In Vivo Use Guide

Female Golden Syrian hamsters have been divided into four groups and treated for 10 weeks as follows: I) Standard diet, containing 0.8 mg cholesterol/g food; II) Standard diet plus HMGA (100 mg/kg b.w./day per os); III) Lithogenic diet containing 2.4 mg cholesterol/g food; IV) Lithogenic diet plus HMGA as above. The results indicate that HMGA is effective in reducing both bile cholesterol supersaturation and hypercholesterolemia.

Route of Administration: Oral

In Vitro Use Guide

Meglutol (5mM) induced lipid peroxidation and decreased GSH concentrations in vitro in rat heart supernatants.

Name

Type

Language

MEGLUTOL

Official Name

English

NSC-361411

Code

English

meglutol [INN]

Common Name

English

CB-337

Code

English

3-Hydroxy-3-methylglutaric acid

Systematic Name

English

MEGLUTOL [USAN]

Common Name

English

MEGLUTOL [MI]

Common Name

English

CB 337

Code

English

MEGLUTOL [MART.]

Common Name

English

PENTANEDIOIC ACID, 3-HYDROXY-3-METHYL-

Common Name

English

Classification Tree Code System Code

WHO-ATC

C10AX05