MEGLUTOL

Possibly Marketed Outside US

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

Molecular Formula	C6H10O5
Molecular Weight	162.1406
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 49 Target ID: CHEMBL402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15686898	Inhibitor 8504		4.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypercholesterolemia 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6180274	Primary		Approved 8583	Lipoglutaren Approved Use Hypolipidemic

PubMed

Title	Date	PubMed
Citrusosides A-D and furanocoumarins with cholinesterase inhibitory activity from the fruit peels of Citrus hystrix.	2010-11-29	20964319
Differential HMG-CoA lyase expression in human tissues provides clues about 3-hydroxy-3-methylglutaric aciduria.	2010-08	20532825
Metabolic profiling reveals local and systemic responses of host plants to nematode parasitism.	2010-06-01	20374527
Inhibition of antigen-induced degranulation by aryl compounds isolated from the bark of Betula platyphylla in RBL-2H3 cells.	2010-05-01	20363129
[Late onset 3-HMG-CoA lyase deficiency: a rare but treatable disorder].	2010-01	19932602
Striatum is more vulnerable to oxidative damage induced by the metabolites accumulating in 3-hydroxy-3-methylglutaryl-CoA lyase deficiency as compared to liver.	2009-06	19460629
Ten novel HMGCL mutations in 24 patients of different origin with 3-hydroxy-3-methyl-glutaric aciduria.	2009-03	19177531
The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides.	2009-01	19155025
Anti-microtubule activity of tubeimoside I and its colchicine binding site of tubulin.	2008-09	18030471
Induction of oxidative stress by the metabolites accumulating in 3-methylglutaconic aciduria in cerebral cortex of young rats.	2008-03-12	18261750
Evidence that 3-hydroxy-3-methylglutaric acid promotes lipid and protein oxidative damage and reduces the nonenzymatic antioxidant defenses in rat cerebral cortex.	2008-02-15	17941049
3-Methylglutaric acid as a 13C solid-state NMR standard.	2006-10	16887343
Flax lignans--analytical methods and how they influence our lunderstanding of biological activity.	2006-08-19	16915858
NMR spectroscopic studies on the late onset form of 3-methylglutaconic aciduria type I and other defects in leucine metabolism.	2006-04	16541463
Crystal structure of human 3-hydroxy-3-methylglutaryl-CoA Lyase: insights into catalysis and the molecular basis for hydroxymethylglutaric aciduria.	2006-03-17	16330550
Metabolomic and bioinformatic analyses in asphyxiated neonates.	2006-03	16460720
A single-residue mutation, G203E, causes 3-hydroxy-3-methylglutaric aciduria by occluding the substrate channel in the 3D structural model of HMG-CoA lyase.	2006-02	16601870
Hypocholesterolemic and antiatherosclerotic effect of flax lignan complex isolated from flaxseed.	2005-04	15777541
Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats.	2004-07	15231000
Fungal metabolic model for 3-methylcrotonyl-CoA carboxylase deficiency.	2004-02-06	14612443
Molecular basis of 3-hydroxy-3-methylglutaric aciduria.	2003-12	15164951
Structural (betaalpha)8 TIM barrel model of 3-hydroxy-3-methylglutaryl-coenzyme A lyase.	2003-08-01	12746442
3-methyglutaconic aciduria in a Chinese patient with glycogen storage disease Ib.	2003	14707520
Biochemical and molecular analyses in three patients with 3-hydroxy-3-methylglutaric aciduria.	2003	14518825
Immunoglobulins and cytokines level in follicular fluid in relation to etiology of infertility and their relevance to IVF outcome.	2002-02	11900592
An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues.	2001-10	11576603
3-Hydroxy-3-methylglutaric aciduria in an Italian patient is caused by a new nonsense mutation in the HMGCL gene.	2001-07	11461194
Mitochondrial DNA depletion associated with partial complex II and IV deficiencies and 3-methylglutaconic aciduria.	2001-02	11292221
Molecular prenatal diagnosis of 3-hydroxy-3-methylglutaryl CoA lyase deficiency.	1995-08	7479590
Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.	1994-06	8087979
Screening newborns for multiple organic acidurias in dried filter paper urine samples: method development.	1991-10	1956713
Studies on a child suspected of having a dficiency in 3-hydroxy-3-methylglutaryl-Co A lyase.	1979-07-02	509721
3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria.	1976-08-02	947633

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:52 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:52 GMT 2025`
Record UNII	CLA99KCD53
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CB 337

Preferred Name

English

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

MEGLUTOL [MART.]

Common Name

English

PENTANEDIOIC ACID, 3-HYDROXY-3-METHYL-

Common Name

English

Classification Tree Code System Code

WHO-ATC

C10AX05