Bempedoic acid

Base Information

• Chemical Name: Bempedoic acid
• CAS No.: 738606-46-7
• Molecular Formula: C19H36O5
• Molecular Weight: 344.492
• European Community (EC) Number: 810-485-8
• UNII: 1EJ6Z6Q368
• DSSTox Substance ID: DTXSID401027952
• Nikkaji Number: J2.071.606A
• Wikipedia: Bempedoic_acid
• Wikidata: Q27075007
• NCI Thesaurus Code: C166494
• RXCUI: 2282403
• Pharos Ligand ID: HWK8BKTA914U
• Metabolomics Workbench ID: 153011
• ChEMBL ID: CHEMBL3545313
• Mol file: 738606-46-7.mol

Synonyms:8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid;bempedoic acid;ESP-55016;ESP55016;ETC-1002;nexletol;nilemdo

Chemical Property of Bempedoic acid

Chemical Property:

• Boiling Point: 506.5±35.0 °C(Predicted)
• PKA: 4.55±0.45(Predicted)
• PSA: 94.83000
• Density: 1.045±0.06 g/cm3(Predicted)
• LogP: 4.46990
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 344.25627424
• Heavy Atom Count: 24
• Complexity: 351

Purity/Quality:

98%, ^*data from raw suppliers

BempedoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CCCCCC(CCCCCC(C)(C)C(=O)O)O)C(=O)O
• Recent ClinicalTrials: A Phase 2 Clinical Study in Children With HeFH Aged 6 to 17 Treated Once Daily With Bempedoic Acid Oral Dosing
• Recent EU Clinical Trials: A prospective, interventional, single-center, single-arm study to assess the effectiveness of Bempedoic acid to achieve LDL-cholesterol targets in patients following ST-elevation or Non-ST-elevation myocardial infarctions insufficiently treated with atorvastatin plus ezetimibe
• Description: Etc-1002 is a small molecule that can be used orally to lower LDL-C and is an activator of LIVER AMPK. ETC-1002 has an effective inhibitory effect on liver ATP-Citrate lyase. ETC-1002 is a prodrug form of ETC-1002-CoA. ETC-1002 is conjugated to coenzyme A (CoA) by very long-chain acyl-CoA synthetase-1 (ACSVL1) to form ETC-1002-CoA, which inhibits ATP citrate lyase (Ki = 2 μM) and activates AMP-activated protein kinase (AMPK). ETC-1002 suppresses total lipid synthesis in wild-type and AMPKβ1 knockout primary murine hepatocytes. In vivo, ETC-1002 (30 mg/kg) prevents increases in hepatic cholesterol and reduces the size of aortic atherosclerotic lesions induced by a high-fat high-cholesterol diet in Apoe-/-/Ampkβ1-/- (DKO) mice.
• Uses: ETC-1002 (Bempedoic acid, ESP-55016),also known as Bempedoic acid, is an orally available, once-daily LDL-C lowering small molecule designed to lower elevated levels of LDL-C and to avoid side effects associated with existing LDL-C lowering therapies.ETC-1002 is an activator of hepatic AMP-activated protein kinase (AMPK). It has potent inhibitory activity against hepatic ATP-citrate lyase(IC50=29 uM).

Technology Process of Bempedoic acid

There total 41 articles about Bempedoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.9%

8-oxo-2,2,14,14-tetramethylpentadecanedioic acid (413624-71-2) → ETC-1002 (738606-46-7)

Guidance literature:

8-oxo-2,2,14,14-tetramethylpentadecanedioic acid; With sodium hydroxide; In water; at 20 ℃; for 0.5h;

With sodium tetrahydroborate; water; for 4h; Reagent/catalyst; Temperature;

Reference yield: 93.5%

C19H38N2O3 → ETC-1002 (738606-46-7)

Guidance literature:

With formic acid; sulfuric acid; at 70 - 80 ℃;

Reference yield: 92.4%

C27H50N2O5 → ETC-1002 (738606-46-7)

Guidance literature:

With ethanol; sulfuric acid; at 70 - 80 ℃;

upstream raw materials:

8-oxo-2,2,14,14-tetramethylpentadecanedioic acid

methyl (3-bromo-2,2-dimethyl) propionate

methyl 6-bromo-2,2-dimethylhexanoate

6-bromo-2,2-dimethyl-hexanoic acid ethyl ester

Refernces

• 1、 -. "Preparation method 8 -hydroxy -2, 2, 14 and 14 -tetramethyl-pentadecanedioic acid". Paragraph 0082-0088. . Retrieved 2021/12/07.
• 2、 -. "Synthetic method of bepidic acid". Paragraph 0033; 0039; 0040; 0046; 0047; 0053. . Retrieved 2021/03/13.