Acipimox

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Also known as: 51037-30-0, Olbetam, 5-carboxy-2-methylpyrazine 1-oxide, Olbemox, 5-methylpyrazine-2-carboxylic acid 4-oxide, 5-methylpyrazinecarboxylic acid 4-oxide

Molecular Formula

C₆H₆N₂O₃

Molecular Weight

154.12 g/mol

InChI Key

DJQOOSBJCLSSEY-UHFFFAOYSA-N

FDA UNII

K9AY9IR2SD

Acipimox is a niacin derivative and nicotinic acid analog with activity as a hypolipidemic agent. Acipimox has special application for the treatment of hyperlipidemia in non-insulin-dependent diabetic patients.

1 2D Structure

Acipimox

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-methyl-4-oxidopyrazin-4-ium-2-carboxylic acid

2.1.2 InChI

InChI=1S/C6H6N2O3/c1-4-2-7-5(6(9)10)3-8(4)11/h2-3H,1H3,(H,9,10)

2.1.3 InChI Key

DJQOOSBJCLSSEY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CN=C(C=[N+]1[O-])C(=O)O

2.2 Other Identifiers

2.2.1 UNII

K9AY9IR2SD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-methylpyrazine-2-carboxylic Acid 4-oxide

2. 5-methylpyrazinecarboxylic Acid 4-oxide

3. Nedios

4. Olbemox

5. Olbetam

2.3.2 Depositor-Supplied Synonyms

1. 51037-30-0

2. Olbetam

3. 5-carboxy-2-methylpyrazine 1-oxide

4. Olbemox

5. 5-methylpyrazine-2-carboxylic Acid 4-oxide

6. 5-methylpyrazinecarboxylic Acid 4-oxide

7. 5-methyl-4-oxidopyrazin-4-ium-2-carboxylic Acid

8. 2-carboxy-5-methylpyrazine 4-oxide

9. K-9321

10. Nsc-759818

11. Chembl345714

12. Ncgc00160519-01

13. Dsstox_cid_26202

14. Dsstox_rid_81433

15. 5-methyl-4-oxido-2-pyrazin-4-iumcarboxylic Acid

16. Dsstox_gsid_46202

17. Cas-51037-30-0

18. Sr-05000001505

19. 5-methyl-2-pyrazinecarboxylic Acid 4-oxide

20. Acipimox-[d4]

21. Mfcd00865757

22. Acipimox (inn/ban)

23. Acipimox [inn]

24. Acipimox [mi]

25. Pyrazinecarboxylic Acid, 5-methyl-, 4-oxide

26. Acipimox [mart.]

27. K9ay9ir2sd

28. Acipimox [who-dd]

29. Schembl48922

30. Gtpl1596

31. Dtxsid2046202

32. Chebi:94688

33. Hms2090g05

34. Hms3655a14

35. Hms3713l18

36. Pharmakon1600-01504831

37. 5-carboxy-2-methylpyrazine1-oxide

38. Bcp28412

39. Hy-b0283

40. Zinc1481960

41. Tox21_111868

42. Tox21_112498

43. Tox21_112805

44. Ac-009

45. Bbl009924

46. Bdbm50208130

47. Nsc759818

48. S1806

49. Stk711089

50. 2-carboxy-5-methyl-pyrazine-4-oxide

51. Akos005530658

52. Ccg-213957

53. Db09055

54. Mb01535

55. 4-oxo-5-methyl-2-pyrazinecarboxylicacid

56. Ncgc00160519-02

57. Ncgc00160519-03

58. As-15565

59. Ba166874

60. 5-methyl-4-oxy-pyrazine-2-carboxylic Acid

61. Ft-0601589

62. M2053

63. Sw199084-2

64. D07190

65. Ab01274727-01

66. Ab01274727-02

67. Ab01274727_03

68. Ab01274727_04

69. K-9321;olbemox;olbetam; K9321; K 9321

70. A828409

71. 5-methyl-4-oxide-2-pyrazinecarboxylic Acid

72. 5-methylpyrazine-2-carboxylic Acid-4-oxide

73. Q2342544

74. Sr-05000001505-1

75. Sr-05000001505-2

76. W-105921

77. Brd-k63736853-001-01-4

2.4 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₆H₆N₂O₃
Molecular Weight	154.12 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	154.03784206 g/mol
Monoisotopic Mass	154.03784206 g/mol
Topological Polar Surface Area	75.6 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	162
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

Used in the treatment of hyperlipidemias (abnormally elevated levels of any or all lipids and/or lipoproteins in the blood).

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

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.)

5.2 ATC Code

C10AD06

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C10 - Lipid modifying agents

C10A - Lipid modifying agents, plain

C10AD - Nicotinic acid and derivatives

C10AD06 - Acipimox

5.3 Mechanism of Action

Acipimox inhibits the production of triglycerides by the liver and the secretion of VLDL, which leads indirectly to a modest reduction in LDL and increase in HDL.