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Chemistry

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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
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 Weight 154.12 g/mol
Molecular Formula C6H6N2O3
XLogP3-1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass154.03784206 g/mol
Monoisotopic Mass154.03784206 g/mol
Topological Polar Surface Area75.6 Ų
Heavy Atom Count11
Formal Charge0
Complexity162
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


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