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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 of MEGLUTOL

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
4.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Lipoglutaren

PubMed

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
Record UNII
CLA99KCD53
Record Status Validated (UNII)
Record Version