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

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 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
Immunoglobulins and cytokines level in follicular fluid in relation to etiology of infertility and their relevance to IVF outcome.	2002 Feb	11900592
Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats.	2004 Jul	15231000
Hypocholesterolemic and antiatherosclerotic effect of flax lignan complex isolated from flaxseed.	2005 Apr	15777541
Flax lignans--analytical methods and how they influence our lunderstanding of biological activity.	2006 Jul-Aug	16915858
Crystal structure of human 3-hydroxy-3-methylglutaryl-CoA Lyase: insights into catalysis and the molecular basis for hydroxymethylglutaric aciduria.	2006 Mar 17	16330550
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
Metabolic profiling reveals local and systemic responses of host plants to nematode parasitism.	2010 Jun 1	20374527
Citrusosides A-D and furanocoumarins with cholinesterase inhibitory activity from the fruit peels of Citrus hystrix.	2010 Nov 29	20964319

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 `Fri Dec 15 15:23:01 GMT 2023` Edited by `admin` on `Fri Dec 15 15:23:01 GMT 2023`
Record UNII	CLA99KCD53
Record Status	`Validated (UNII)`
Record Version

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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