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
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)
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15686898 |
4.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Lipoglutaren Approved UseHypolipidemic |
PubMed
Title | Date | PubMed |
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3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. | 1976 Aug 2 |
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Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. | 1994 Jun |
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Mitochondrial DNA depletion associated with partial complex II and IV deficiencies and 3-methylglutaconic aciduria. | 2001 Feb |
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Biochemical and molecular analyses in three patients with 3-hydroxy-3-methylglutaric aciduria. | 2003 |
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Structural (betaalpha)8 TIM barrel model of 3-hydroxy-3-methylglutaryl-coenzyme A lyase. | 2003 Aug 1 |
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Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats. | 2004 Jul |
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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 |
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Anti-microtubule activity of tubeimoside I and its colchicine binding site of tubulin. | 2008 Sep |
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The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides. | 2009 Jan |
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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 |
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Ten novel HMGCL mutations in 24 patients of different origin with 3-hydroxy-3-methyl-glutaric aciduria. | 2009 Mar |
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Metabolic profiling reveals local and systemic responses of host plants to nematode parasitism. | 2010 Jun 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6180274
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27430492
Meglutol (5mM) induced lipid peroxidation and decreased GSH
concentrations in vitro in rat heart supernatants.
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C10AX05
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QC10AX05
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ACTIVE MOIETY