Bempedoic acid
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MedKoo CAT#: 319651

CAS#: 738606-46-7

Description: Bempedoic acid, also known as ESP-55016 and ETC-1002, 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. Bempedoic acid is absorbed rapidly in the small intestine and enters the liver through cell surface receptors different from those transporters that selectively take up statins. Bempedoic acid is a regulator of lipid and carbohydrate metabolism.

Chemical Structure

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Bempedoic acid
CAS# 738606-46-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319651
Name: Bempedoic acid
CAS#: 738606-46-7
Chemical Formula: C19H36O5
Exact Mass: 344.26
Molecular Weight: 344.492
Elemental Analysis: C, 66.25; H, 10.53; O, 23.22

Price and Availability

Size Price Availability Quantity
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 800 Ready to ship
500mg USD 1850 Ready to ship
1g USD 3250 Ready to ship
Bulk inquiry

Synonym: ESP-55016; ESP55016; ESP 55016; ETC-1002; ETC 1002; ETC1002; Bempedoate; Bempedoic acid

IUPAC/Chemical Name: 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid

InChi Key: HYHMLYSLQUKXKP-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H36O5/c1-18(2,16(21)22)13-9-5-7-11-15(20)12-8-6-10-14-19(3,4)17(23)24/h15,20H,5-14H2,1-4H3,(H,21,22)(H,23,24)

SMILES Code: O=C(O)C(C)(C)CCCCCC(O)CCCCCC(C)(C)C(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Bempedoic acid (ETC-1002) is an ATP-citrate lyase (ACL) inhibitor and also serves to activate AMPK.
In vitro activity: In human hepatocellular carcinoma (HepG2) cells treated with bempedoic acid (ETC-1002), profound and concentration-dependent activation of AMPK has been previously attributed to ETC-1002-free acid as, similar to primary human MDMs, these cells do not metabolize parent molecules to ETC-1002-CoA thioester. To determine whether ETC-1002 activates AMPK in human macrophages, MDMs differentiated in autologous serum were treated with various concentrations of the compound, and cell lysates were probed with anti-phosphorylated AMPKα (T172) antibody. In vehicle-treated MDMs, basal levels of AMPK phosphorylation were readily detectible as demonstrated by the appearance of an immunoreactive band corresponding to the expected molecular mass of ∼62 kDa (Fig. 1B). Concentration-dependent increases in phospho-AMPK-to-total-AMPK ratio in ETC-1002-treated cells indicate that ETC-1002 induces AMPK (T172) phosphorylation at levels comparable to those observed previously in HepG2 cells. ACC (serine 79) is a unique AMPK phosphorylation site and is commonly used as a marker of AMPK activity. As such, when cell lysates from MDMs treated with ETC-1002 were probed with anti-phosphorylated ACC (S79) antibodies, sustained and concentration-dependent increases in ACC (S79)-specific immunoreactivity were observed at the expected molecular mass of ∼280 kDa. Consistently, the phospho-ACC to total-ACC ratio increased by 25% and 60% in cells treated with 50 µM and 100 µM ETC-1002, respectively (Fig. 1B). Taken together, these data confirm the AMPK-activating properties of ETC-1002 in primary human MDMs (Fig. 1B). Reference: J Lipid Res. 2013 Aug;54(8):2095-2108. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/23709692/
In vivo activity: In a mouse model of DIO, a two-week treatment with ETC-1002 was sufficient to reduce body weight as well as to lower fasting plasma glucose and insulin levels. Since adipose tissue macrophages are believed to play a critical role in governing immune responses and insulin resistance in DIO, it was next evaluated whether the beneficial effect of ETC-1002 on glycemic control can be linked to reduced levels of adipose tissue-associated inflammation. As such, male C57BL/6 mice were placed on HFD and orally dosed with either vehicle alone or ETC-1002 at 30 mg/kg/day for nine weeks. At the termination of the study, visceral adipose tissue from mice placed on HFD was macroscopically larger (Fig. 8A), with the average epididymal fat pad mass significantly increased relative to chow-fed animals (0.31 ± 0.04 g, chow-fed versus 1.3 ± 0.04 g, HFD-fed; P < 0.05) (Fig. 7A). By contrast, ETC-1002-treated mice displayed a 32% reduction in fat-pad mass (fat-pad mass: 1.3 ± 0.04 g, HFD-fed versus 0.89 ± 0.07 g, HFD-fed/ETC-1002; P < 0.05). Reference: J Lipid Res. 2013 Aug;54(8):2095-2108. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/23709692/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 68.0 197.39

Preparing Stock Solutions

The following data is based on the product molecular weight 344.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Filippov S, Pinkosky SL, Lister RJ, Pawloski C, Hanselman JC, Cramer CT, Srivastava RAK, Hurley TR, Bradshaw CD, Spahr MA, Newton RS. ETC-1002 regulates immune response, leukocyte homing, and adipose tissue inflammation via LKB1-dependent activation of macrophage AMPK. J Lipid Res. 2013 Aug;54(8):2095-2108. doi: 10.1194/jlr.M035212. Epub 2013 May 24. PMID: 23709692; PMCID: PMC3708360. 2. Pinkosky SL, Filippov S, Srivastava RA, Hanselman JC, Bradshaw CD, Hurley TR, Cramer CT, Spahr MA, Brant AF, Houghton JL, Baker C, Naples M, Adeli K, Newton RS. AMP-activated protein kinase and ATP-citrate lyase are two distinct molecular targets for ETC-1002, a novel small molecule regulator of lipid and carbohydrate metabolism. J Lipid Res. 2013 Jan;54(1):134-51. doi: 10.1194/jlr.M030528. Epub 2012 Nov 1. PMID: 23118444; PMCID: PMC3520520.
In vivo protocol: 1. Filippov S, Pinkosky SL, Lister RJ, Pawloski C, Hanselman JC, Cramer CT, Srivastava RAK, Hurley TR, Bradshaw CD, Spahr MA, Newton RS. ETC-1002 regulates immune response, leukocyte homing, and adipose tissue inflammation via LKB1-dependent activation of macrophage AMPK. J Lipid Res. 2013 Aug;54(8):2095-2108. doi: 10.1194/jlr.M035212. Epub 2013 May 24. PMID: 23709692; PMCID: PMC3708360. 2. Pinkosky SL, Filippov S, Srivastava RA, Hanselman JC, Bradshaw CD, Hurley TR, Cramer CT, Spahr MA, Brant AF, Houghton JL, Baker C, Naples M, Adeli K, Newton RS. AMP-activated protein kinase and ATP-citrate lyase are two distinct molecular targets for ETC-1002, a novel small molecule regulator of lipid and carbohydrate metabolism. J Lipid Res. 2013 Jan;54(1):134-51. doi: 10.1194/jlr.M030528. Epub 2012 Nov 1. PMID: 23118444; PMCID: PMC3520520.

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1: Lemus HN, Mendivil CO. Adenosine triphosphate citrate lyase: Emerging target in the treatment of dyslipidemia. J Clin Lipidol. 2015 May-Jun;9(3):384-9. doi: 10.1016/j.jacl.2015.01.002. Epub 2015 Jan 14. Review. PubMed PMID: 26073398.

2: Thompson PD, Rubino J, Janik MJ, MacDougall DE, McBride SJ, Margulies JR, Newton RS. Use of ETC-1002 to treat hypercholesterolemia in patients with statin intolerance. J Clin Lipidol. 2015 May-Jun;9(3):295-304. doi: 10.1016/j.jacl.2015.03.003. Epub 2015 Mar 19. PubMed PMID: 26073387.

3: Nikolic D, Mikhailidis DP, Davidson MH, Rizzo M, Banach M. ETC-1002: a future option for lipid disorders? Atherosclerosis. 2014 Dec;237(2):705-10. doi: 10.1016/j.atherosclerosis.2014.10.099. Epub 2014 Oct 31. Review. PubMed PMID: 25463109.

4: Filippov S, Pinkosky SL, Newton RS. LDL-cholesterol reduction in patients with hypercholesterolemia by modulation of adenosine triphosphate-citrate lyase and adenosine monophosphate-activated protein kinase. Curr Opin Lipidol. 2014 Aug;25(4):309-15. doi: 10.1097/MOL.0000000000000091. Review. PubMed PMID: 24978142; PubMed Central PMCID: PMC4162331.

5: Goldberg R. Targeting low-density lipoprotein and dysmetabolism in type 2 diabetes mellitus. Arterioscler Thromb Vasc Biol. 2014 Mar;34(3):477-8. doi: 10.1161/ATVBAHA.114.303171. PubMed PMID: 24554605; PubMed Central PMCID: PMC4067598.

6: Gutierrez MJ, Rosenberg NL, Macdougall DE, Hanselman JC, Margulies JR, Strange P, Milad MA, McBride SJ, Newton RS. Efficacy and safety of ETC-1002, a novel investigational low-density lipoprotein-cholesterol-lowering therapy for the treatment of patients with hypercholesterolemia and type 2 diabetes mellitus. Arterioscler Thromb Vasc Biol. 2014 Mar;34(3):676-83. doi: 10.1161/ATVBAHA.113.302677. Epub 2014 Jan 2. PubMed PMID: 24385236.

7: Ballantyne CM, Davidson MH, Macdougall DE, Bays HE, Dicarlo LA, Rosenberg NL, Margulies J, Newton RS. Efficacy and safety of a novel dual modulator of adenosine triphosphate-citrate lyase and adenosine monophosphate-activated protein kinase in patients with hypercholesterolemia: results of a multicenter, randomized, double-blind, placebo-controlled, parallel-group trial. J Am Coll Cardiol. 2013 Sep 24;62(13):1154-62. doi: 10.1016/j.jacc.2013.05.050. Epub 2013 Jun 13. PubMed PMID: 23770179.

8: Kane JP. New horizons in lipid management. J Am Coll Cardiol. 2013 Sep 24;62(13):1163-4. doi: 10.1016/j.jacc.2013.05.052. Epub 2013 Jun 13. PubMed PMID: 23770169.

9: Filippov S, Pinkosky SL, Lister RJ, Pawloski C, Hanselman JC, Cramer CT, Srivastava RA, Hurley TR, Bradshaw CD, Spahr MA, Newton RS. ETC-1002 regulates immune response, leukocyte homing, and adipose tissue inflammation via LKB1-dependent activation of macrophage AMPK. J Lipid Res. 2013 Aug;54(8):2095-108. doi: 10.1194/jlr.M035212. Epub 2013 May 24. PubMed PMID: 23709692; PubMed Central PMCID: PMC3708360.

10: Norata GD, Ballantyne CM, Catapano AL. New therapeutic principles in dyslipidaemia: focus on LDL and Lp(a) lowering drugs. Eur Heart J. 2013 Jun;34(24):1783-9. doi: 10.1093/eurheartj/eht088. Epub 2013 Mar 18. Review. PubMed PMID: 23509227; PubMed Central PMCID: PMC3857929.

11: Pinkosky SL, Filippov S, Srivastava RA, Hanselman JC, Bradshaw CD, Hurley TR, Cramer CT, Spahr MA, Brant AF, Houghton JL, Baker C, Naples M, Adeli K, Newton RS. AMP-activated protein kinase and ATP-citrate lyase are two distinct molecular targets for ETC-1002, a novel small molecule regulator of lipid and carbohydrate metabolism. J Lipid Res. 2013 Jan;54(1):134-51. doi: 10.1194/jlr.M030528. Epub 2012 Nov 1. PubMed PMID: 23118444; PubMed Central PMCID: PMC3520520.