738606-46-7

Basic information

• Product Name: ETC-1002
• Synonyms: ETC-1002;Bempedoic Acid;ETC-1002 (ESP 55016);ESP 55016
• CAS NO: 738606-46-7
• Molecular Formula: C₁₉H₃₆O₅
• Molecular Weight: 344.48614
• Product Categories: API
• Mol File: 738606-46-7.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 506.5±35.0 °C(Predicted)
• Appearance: /
• Density: 1.045±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.55±0.45(Predicted)
• CAS DataBase Reference: ETC-1002(CAS DataBase Reference)
• NIST Chemistry Reference: ETC-1002(738606-46-7)
• EPA Substance Registry System: ETC-1002(738606-46-7)

Safety Data

• Hazardous Substances Data: 738606-46-7(Hazardous Substances Data)

Usage

Description

ETC-1002, also known as Bempedoic acid or ESP-55016, is an orally available, once-daily small molecule designed to lower elevated levels of LDL-C (low-density lipoprotein cholesterol) and avoid side effects associated with existing LDL-C lowering therapies. It is an activator of hepatic AMP-activated protein kinase (AMPK) and has potent inhibitory activity against hepatic ATP-citrate lyase. ETC-1002 is a prodrug form that, when conjugated to coenzyme A (CoA) by very long-chain acyl-CoA synthetase-1 (ACSVL1), forms ETC-1002-CoA, which further inhibits ATP citrate lyase and activates AMPK. This molecule effectively suppresses total lipid synthesis in primary murine hepatocytes and has been shown to prevent increases in hepatic cholesterol and reduce the size of aortic atherosclerotic lesions in vivo.

Uses

Used in Pharmaceutical Industry:
ETC-1002 is used as a LDL-C lowering agent for patients with elevated levels of LDL-C, aiming to reduce the risk of cardiovascular diseases and improve overall health.
Used in Cardiovascular Disease Management:
ETC-1002 is used as a therapeutic agent for the prevention and treatment of atherosclerotic lesions, particularly in patients with a high-fat high-cholesterol diet, by reducing hepatic cholesterol and the size of aortic atherosclerotic lesions.
Used in Research and Development:
ETC-1002 is used as a research tool for studying the mechanisms of LDL-C regulation, AMPK activation, and ATP-citrate lyase inhibition, contributing to the development of novel therapies for metabolic and cardiovascular diseases.

Upstream product

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Relevant articles and documents

Preparation method of bepiridic acid

The invention relates to a preparation method of bepiridic acid, and the method comprises the following process steps: (1) synthesis of an intermediate BP-B: dissolving a compound A in nitromethane, and carrying out nucleophilic reaction under alkaline conditions to obtain the intermediate BP-B; (2) synthesis of an intermediate BP-C: carrying out a Nef Reaction reaction on the intermediate BP-B obtained in the step (1) under an alkaline condition to obtain the intermediate BP-C; (3) synthesis of beparidic: carrying out a reduction reaction on the intermediate BP-C obtained in the step (2) and a reducing agent to obtain the beparidic. In the second-step reaction of the process, use of an expensive p-toluenesulfonyl methyl isocyanide reagent is avoided. The third-step reaction of the process avoids the use of column chromatography separation, and is more suitable for industrial production.

Synthesis of bempedoic acid through electrochemical decarboxylation of dialkylated malonic acid

Bempedoic acid is a small-molecule inhibitor of adenosine triphosphate-citrate lyase (ACL) that is effective in the treatment of hypercholesterolemia and hypertension. In this paper, a new, six-step synthesis of bempedoic acid with 42% overall yield is reported. Ketone formation by electrochemical decarboxylation of dialkylated malonic acid is introduced as the key step of this process. This method uses mild conditions and its high efficiency makes it potentially suitable for industrial production.

Preparation method of Bempedoic acid

The invention discloses a preparatino method ofBempedoic acid. The preparation method comprises the following steps: carrying out condensation reaction on ethyl isobutyrate and 2-(5-bromo-n-amyl)-1, 3-dioxocyclopentane under the effect of an alkali accelerator, carrying out hydrolysis reaction to obtain an intermediate 8-oxa-2, 2-dimethyl octanoic acid, and carrying out Grignard reaction on the intermediate and 7-bromo-2, 2-dimethyl heptanoic acid to obtain the Bempedoic acid. The preparation method is simple in process, mild in condition, safe and environment-friendly, and provides a new way for industrial production.