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    Mevastatin

    ACTIVE PHARMA INGREDIENTS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    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

    2D Structure

    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 Weight 390.5 g/mol
    Molecular Formula C23H34O5
    XLogP33.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass390.24062418 g/mol
    Monoisotopic Mass390.24062418 g/mol
    Topological Polar Surface Area72.8 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity637
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    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

    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.