Meglutol
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Identification
- Generic Name
- Meglutol
- DrugBank Accession Number
- DB04377
- Background
An antilipemic agent which lowers cholesterol, triglycerides, serum beta-lipoproteins and phospholipids. It acts by interfering with the enzymatic steps involved in the conversion of acetate to hydroxymethylglutaryl coenzyme A as well as inhibiting the activity of HYDROXYMETHYLGLUTARYL COA REDUCTASES which is the rate limiting enzyme in the biosynthesis of cholesterol.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 162.1406
Monoisotopic: 162.05282343 - Chemical Formula
- C6H10O5
- Synonyms
- 3-hydroxy-3-methylglutaric acid
- Dicrotalic acid
- Meglutol
- External IDs
- CB 337
- CB-337
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U3-hydroxy-3-methylglutaryl-coenzyme A reductase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
Categories
- ATC Codes
- C10AX05 — Meglutol
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- Direct Parent
- Hydroxy fatty acids
- Alternative Parents
- Short-chain hydroxy acids and derivatives / Methyl-branched fatty acids / Dicarboxylic acids and derivatives / Tertiary alcohols / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alcohol / Aliphatic acyclic compound / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Hydrocarbon derivative / Hydroxy fatty acid / Methyl-branched fatty acid
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- tertiary alcohol, dicarboxylic acid, 3-hydroxy carboxylic acid (CHEBI:16831)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- CLA99KCD53
- CAS number
- 503-49-1
- InChI Key
- NPOAOTPXWNWTSH-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)
- IUPAC Name
- 3-hydroxy-3-methylpentanedioic acid
- SMILES
- CC(O)(CC(O)=O)CC(O)=O
References
- Synthesis Reference
Luigi Turbanti, Giorgio Garzelli, "Process for preparation of 3-hydroxy-3-methyl-glutaric acid." U.S. Patent US4966993, issued October, 1985.
US4966993- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000355
- KEGG Drug
- D04897
- KEGG Compound
- C03761
- PubChem Compound
- 1662
- PubChem Substance
- 46508063
- ChemSpider
- 1600
- BindingDB
- 50160720
- ChEBI
- 16831
- ChEMBL
- CHEMBL50444
- ZINC
- ZINC000000001669
- PDBe Ligand
- MAH
- Wikipedia
- Meglutol
- PDB Entries
- 1dq8 / 1dqa / 2liw
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 275.0 mg/mL ALOGPS logP -0.88 ALOGPS logP -0.75 Chemaxon logS 0.23 ALOGPS pKa (Strongest Acidic) 3.68 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 94.83 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 34.14 m3·mol-1 Chemaxon Polarizability 14.55 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6339 Blood Brain Barrier + 0.9359 Caco-2 permeable - 0.657 P-glycoprotein substrate Non-substrate 0.5874 P-glycoprotein inhibitor I Non-inhibitor 0.967 P-glycoprotein inhibitor II Non-inhibitor 0.9396 Renal organic cation transporter Non-inhibitor 0.9581 CYP450 2C9 substrate Non-substrate 0.7836 CYP450 2D6 substrate Non-substrate 0.8892 CYP450 3A4 substrate Non-substrate 0.6472 CYP450 1A2 substrate Non-inhibitor 0.9103 CYP450 2C9 inhibitor Non-inhibitor 0.9173 CYP450 2D6 inhibitor Non-inhibitor 0.9444 CYP450 2C19 inhibitor Non-inhibitor 0.9203 CYP450 3A4 inhibitor Non-inhibitor 0.8487 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9781 Ames test Non AMES toxic 0.9445 Carcinogenicity Non-carcinogens 0.6285 Biodegradation Ready biodegradable 0.551 Rat acute toxicity 1.9397 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9877 hERG inhibition (predictor II) Non-inhibitor 0.9734
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 135.4825468 predictedDarkChem Lite v0.1.0 [M-H]- 135.6270468 predictedDarkChem Lite v0.1.0 [M-H]- 135.6421468 predictedDarkChem Lite v0.1.0 [M-H]- 123.32347 predictedDeepCCS 1.0 (2019) [M+H]+ 136.3067468 predictedDarkChem Lite v0.1.0 [M+H]+ 137.9334468 predictedDarkChem Lite v0.1.0 [M+H]+ 137.3292468 predictedDarkChem Lite v0.1.0 [M+H]+ 127.15436 predictedDeepCCS 1.0 (2019) [M+Na]+ 135.1681468 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.2414468 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.1089468 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.74873 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nadph binding
- Specific Function
- Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including...
- Gene Name
- HMGCR
- Uniprot ID
- P04035
- Uniprot Name
- 3-hydroxy-3-methylglutaryl-coenzyme A reductase
- Molecular Weight
- 97475.155 Da
References
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51