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Bempedoic Acid

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Chemistry

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Also known as: Etc-1002, 738606-46-7, 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid, Nexletol, Esp-55016, Nilemdo

Molecular Formula

C₁₉H₃₆O₅

Molecular Weight

344.5 g/mol

InChI Key

HYHMLYSLQUKXKP-UHFFFAOYSA-N

FDA UNII

1EJ6Z6Q368

High levels of LDL cholesterol (LDL-C) are a major risk factor for cardiovascular events. Caused by genetic mutations or lifestyle factors, hypercholesterolemia can significantly reduce quality of life and increase the risk of mortality from cardiovascular disease. About 1 in 4 patients, or 15 million Americans with elevated LDL-C, are insufficiently managed with maximally tolerated statin therapy alone, requiring additional treatment for hypercholesterolemia. Bempedoic acid is first-in-class adenosine triphosphate-citrate lyase (ACL) inhibitor used once a day for reducing LDL cholesterol levels in statin-refractory patients. It was developed by Esperion Therapeutics Inc. and approved by the FDA on February 21, 2020. A combination product of bempedoic acid and [ezetimibe] was approved on February 26, 2020 for increased control of LDL cholesterol levels in patients experiencing refractory elevations despite previous statin treatment.

Bempedoic acid is an Adenosine Triphosphate-Citrate Lyase Inhibitor. The mechanism of action of bempedoic acid is as an Adenosine Triphosphate-Citrate Lyase Inhibitor.

1 2D Structure

Bempedoic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid

2.1.2 InChI

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)

2.1.3 InChI Key

HYHMLYSLQUKXKP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(CCCCCC(CCCCCC(C)(C)C(=O)O)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

1EJ6Z6Q368

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic Acid

2. Esp-55016

3. Esp55016

4. Etc-1002

5. Nexletol

6. Nilemdo

2.3.2 Depositor-Supplied Synonyms

1. Etc-1002

2. 738606-46-7

3. 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic Acid

4. Nexletol

5. Esp-55016

6. Nilemdo

7. Etc1002

8. Etc 1002

9. Esp 55016

10. 1ej6z6q368

11. Mfcd18800820

12. Etc-1002;esp-55016

13. Pentadecanedioic Acid, 8-hydroxy-2,2,14,14-tetramethyl-

14. Bempedoate

15. Unii-1ej6z6q368

16. Bempedoic Acid [usan:inn]

17. Bempedoic-acid

18. Bempedoic Acid

19. Esp-55016

20. Acido Bempedoico

21. Acide Bempedoique

22. Acidum Bempedoicum

23. Nexletol (tn)

24. Bempedoic Acid (usan/inn)

25. Bempedoic Acid [inn]

26. Bempedoic Acid [jan]

27. Bempedoic Acid [usan]

28. Schembl185768

29. Gtpl8321

30. Bempedoic Acid [who-dd]

31. Chembl3545313

32. Chebi:149601

33. Dtxsid401027952

34. Amy31933

35. Bcp16083

36. Esp55016

37. Ex-a1243

38. Zinc3948738

39. Bempedoic Acid [orange Book]

40. S7953

41. Akos027439916

42. Ccg-267969

43. Cs-3952

44. Db11936

45. Nexlizet Component Bempedoic Acid

46. Ac-29040

47. As-49804

48. Hy-12357

49. Sy244715

50. Bempedoic Acid Component Of Nexlizet

51. Bempedoic Acid(etc-1002;esp-55016)

52. Db-108321

53. D10691

54. N10681

55. A905695

56. Q27075007

57. 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic Acid;etc-1002

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₃₆O₅
Molecular Weight	344.5 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	14
Exact Mass	344.25627424 g/mol
Monoisotopic Mass	344.25627424 g/mol
Topological Polar Surface Area	94.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	351
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Bempedoic acid is indicated as an adjunct to diet and maximally tolerated statin therapy for adults with heterozygous familial hypercholesterolemia or existing atherosclerotic cardiovascular disease that warrants additional lowering of LDL-C. The combination of bempedoic and ezetimibe is also indicated with diet management and maximally tolerated statin therapy to treat elevated LDL-C levels in adults with heterozygous familial hypercholesterolemia or existing atherosclerotic cardiovascular disease who require further lowering of LDL-C.

FDA Label

Nilemdo is indicated in adults with primary hypercholesterolaemia (heterozygous familial and non familial) or mixed dyslipidaemia, as an adjunct to diet:

- in combination with a statin or statin with other lipid-lowering therapies in patients unable to reach LDL C goals with the maximum tolerated dose of a statin (see sections 4. 2, 4. 3, and 4. 4) or,

- alone or in combination with other lipid-lowering therapies in patients who are statin intolerant, or for whom a statin is contraindicated.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bempedoic acid inhibits the synthesis of cholesterol in the liver, reducing LDL-C levels. This reduces the development of atherosclerotic plaques that may increase the risk of cardiovascular events. Earlier clinical trials studying the effects of bempedoic acid showed a dosedependent reduction of LDLC levels in addition to decreased LDL particle number, and reduced levels of apolipoprotein B, nonHDL cholesterol, and highsensitivity Creactive protein. Due to its unique mechanism of action, bempedoic acid is not associated with myositis, an adverse effect that frequently accompanies statin therapy. More recent trials have supported that this drug significantly decreases LDL-C levels after 12 weeks of therapy and provides additional lowering of LDL-C when combined with ezetimibe and statin therapy. The effects of bempedoic acid on mortality are currently unknown.

5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Hypoglycemic Agents

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

Hypolipidemic Agents

Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS. (See all compounds classified as Hypolipidemic Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

BEMPEDOIC ACID

5.3.2 FDA UNII

1EJ6Z6Q368

5.3.3 Pharmacological Classes

Adenosine Triphosphate-Citrate Lyase Inhibitors [MoA]; Adenosine Triphosphate-Citrate Lyase Inhibitor [EPC]

5.4 ATC Code

C10AX

C - Cardiovascular system

C10 - Lipid modifying agents

C10A - Lipid modifying agents, plain

C10AX - Other lipid modifying agents

C10AX15 - Bempedoic acid

5.5 Absorption, Distribution and Excretion

Absorption

Bempedoic acid is rapidly absorbed in the small intestine. The Tmax of the 180mg tablet is estimated at 3.5 hours.

Route of Elimination

Bempedoic acid's conjugates are primarily eliminated via the urine (70%) and the feces (30%). A total of 5% of the unchanged drug is excreted in the urine and feces, combined.

Volume of Distribution

The apparent volume of distribution of bempedoic acid is about 18L.

Clearance

The clearance (CL/F) of bempedoic acid at steady state was estimated at 11.2 mL/min during clinical trials.

5.6 Metabolism/Metabolites

The two main metabolites of bempedoic metabolism are ETC-1002-CoA and ESP15228. Bempedoic acid is primarily eliminated via the metabolism of its acyl glucuronide. This drug is reversibly converted to an active metabolite (ESP15228) based on observations during in vitro studies. Both compounds resulting from the metabolism of bempedoic acid are metabolized to become inactive glucuronide conjugates by the enzyme UGT2B7.

5.7 Biological Half-Life

The half-life of bempedoic acid ranges between 15 and 24 hours. Prescribing information indicates a clearance of 21 hours +/- 11 hours.

5.8 Mechanism of Action

Normally, LDL cholesterol is produced in the liver and circulates in the blood. When the blood becomes saturated, excess LDL deposits in blood vessels including the coronary arteries, increasing the risk of cardiovascular events. Bempedoic acid is a prodrug that requires activation in the liver. The very-long-chain acyl-CoA synthetase-1 (ACSVL1) enzyme is responsible for its activation to ETC-1002-CoA, the pharmacologically active metabolite. ATP lyase (also known as ATP synthase) plays an important part of cholesterol synthesis. BETC-1002-CoA directly inhibits this enzyme after the parent drug is activated in the liver by coenzyme A (CoA). This inhibition leads to upregulation of the LDL cholesterol receptor, reducing serum LDL-C via increased uptake and LDL clearance in the liver. By the above mechanisms, bempedoic acid causes a total decrease of circulating LDL-C that normally damages blood vessels and leads to atherosclerosis. Lastly, ETC-1002 activates AMP-activated protein kinase (AMPK) in rodents, which inhibits the synthesis of cholesterol via the inhibition of HMG-CoA reductase. The relevance of this to humans is unknown.

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Kimia Biosciences

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American Pharma Summit

Not Confirmed

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API Reference Price

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