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Mevastatin

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Chemistry

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Also known as: 73573-88-3, Compactin, Ec 700-442-0, Ml-236b, Mevastatin [inn], Mevastatina

Molecular Formula

C₂₃H₃₄O₅

Molecular Weight

390.5 g/mol

InChI Key

AJLFOPYRIVGYMJ-INTXDZFKSA-N

FDA UNII

1UQM1K0W9X

Mevastatin is an HMG-CoA reductase inhibitor that was initially isolated from the mold Pythium ultimum. Mevastatin was the first statin to enter clinical trials.

1 2D Structure

Mevastatin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate

2.1.2 InChI

InChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1

2.1.3 InChI Key

AJLFOPYRIVGYMJ-INTXDZFKSA-N

2.1.4 Canonical SMILES

CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O

2.1.5 Isomeric SMILES

CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O

2.2 Other Identifiers

2.2.1 UNII

1UQM1K0W9X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-demethylmevinolin

2. Compactin

3. Cs 500

4. Ml 236b

5. Ml-236b

6. Ml236b

2.3.2 Depositor-Supplied Synonyms

1. 73573-88-3

2. Compactin

3. Ec 700-442-0

4. Ml-236b

5. Mevastatin [inn]

6. Mevastatina

7. Mevastatine

8. Mevastatinum

9. Mevastatinum [inn-latin]

10. Antibiotic Ml 236b

11. Cs 500

12. Ml 236 B

13. [(1s,7s,8s,8ar)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2s)-2-methylbutanoate

14. 1uqm1k0w9x

15. Mevastatin (compactin)

16. Chembl54440

17. Chebi:34848

18. Ml236b

19. Nsc-759322

20. (1s,7s,8s,8ar)-1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-((2r,4r)-tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl)ethyl)-1-naphthyl (s)-2-methylbutyrate

21. Compactin (penicillium)

22. Mevastatine [inn-french]

23. Mevastatina [inn-spanish]

24. (1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (s)-2-methylbutanoate

25. (s)-((1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate

26. Butanoic Acid, 2-methyl-, (1s,7s,8s,8ar)-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-[(2r,4r)-tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl]ethyl]-1-naphthalenyl Ester, (2s)-

27. Smr000336944

28. Ccris 4505

29. Unii-1uqm1k0w9x

30. Kompaktin

31. Ncgc00095942-01

32. Mevastatin- Bio-x

33. Mfcd05662341

34. Mevastatin [mi]

35. Mevastatin [jan]

36. Mevastatin [mart.]

37. Schembl1116

38. Dsstox_cid_20684

39. Dsstox_rid_79540

40. Mevastatin [usp-rs]

41. Dsstox_gsid_40684

42. Lopac0_000754

43. Mls000721804

44. Mls000759452

45. Mls001424284

46. Mls002207227

47. Gtpl3031

48. Dtxsid4040684

49. Mevastatin, >=96% (hplc)

50. Hms2052p07

51. Hms2089d10

52. Hms2232n09

53. Hms3262g10

54. Hms3268a19

55. Hms3412h15

56. Hms3676h15

57. Hms3713b06

58. Zinc3833876

59. Tox21_111540

60. Tox21_500754

61. Bdbm50011036

62. Cs-500

63. Nsc779705

64. S4223

65. Akos015994712

66. Mevastatin, >=95% (hplc), Powder

67. Ccg-101174

68. Cs-1234

69. Db06693

70. Ks-1085

71. Lp00754

72. Nc00424

73. Nsc 759322

74. Nsc-779705

75. Sdccgsbi-0050732.p002

76. 7-(1,2,6,7,8,8a-hexahydro-2-methyl-8-(2-methylbutyryloxy)naphthyl)-3-hydroxyheptan-5-olide

77. Smp1_000077

78. Ncgc00025202-04

79. Ncgc00261439-01

80. (1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl(2s)-2-methylbutanoate

81. Bm164666

82. Butanoic Acid, 2-methyl-, (1s,7s,8s,8ar)-1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl)ethyl)-1-naphthalenyl Ester, (2s)-

83. Butanoic Acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl)ethyl)-1-naphthalenyl Ester, (1s-(1-alpha(r*),7-beta,8-beta(2s*,4s*),8a-beta))-

84. Hy-17408

85. Mevastatin 100 Microg/ml In Acetonitrile

86. Cas-73573-88-3

87. Lovastatin Impurity A [ep Impurity]

88. B1788

89. Eu-0100754

90. M2275

91. H11997

92. M 2537

93. Ab00588266-06

94. Ab00588266-08

95. Ab00588266_09

96. 573m883

97. A837861

98. Q414407

99. Sr-01000729493

100. L-637312

101. Sr-01000729493-4

102. Brd-k94441233-001-03-1

103. Brd-k94441233-001-17-1

104. (1s,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2s)-2-methylbutanoate

105. (s)-((1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxo-tetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate

106. (s)-2-methyl-butyric Acid (1s,7s,8s,8ar)-8-[2-((2r,4r)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester

107. 2-methyl-butyric Acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester

108. 2-methyl-butyric Acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester((+)-compactin)

109. 2-methyl-butyric Acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester(compactin)

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₄O₅
Molecular Weight	390.5 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	390.24062418 g/mol
Monoisotopic Mass	390.24062418 g/mol
Topological Polar Surface Area	72.8 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	637
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
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

Not used therapeutically due to its many side effects.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The primary cause of cardiovascular disease is atherosclerotic plaque formation. Mevastatin lowers hepatic production of cholesterol to reduce the risk of cardiovascular disease. Mevastatin competitively inhibits HMG-CoA reductase. This inhibition prevents the rate limiting step in cholesterol synthesis. Decreased hepatic cholesterol levels causes increased uptake of low density lipoprotein (LDL) cholesterol and reduces cholesterol levels in the circulation.

5.2 MeSH Pharmacological Classification

Anticholesteremic Agents

Substances used to lower plasma cholesterol levels. (See all compounds classified as Anticholesteremic Agents.)

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Hydroxymethylglutaryl-CoA Reductase Inhibitors

Compounds that inhibit HYDROXYMETHYLGLUTARYL COA REDUCTASES. They have been shown to directly lower CHOLESTEROL synthesis. (See all compounds classified as Hydroxymethylglutaryl-CoA Reductase Inhibitors.)

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

5.3 Mechanism of Action

Mevastatin is structurally similar to the HMG, a substituent of the endogenous substrate of HMG-CoA reductase. Mevastatin is a prodrug that is activated in vivo via hydrolysis of the lactone ring. The hydrolyzed lactone ring mimics the tetrahedral intermediate produced by the reductase allowing the agent to bind with 10,000 times greater affinity than its natural substrate. The bicyclic portion of mevastatin binds to the coenzyme A portion of the active site.

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