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Chemistry

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Also known as: 81131-70-6, Pravachol, Mevalotin, Selektine, Elisor, Pravaselect
Molecular Formula
C23H35NaO7
Molecular Weight
446.5  g/mol
InChI Key
VWBQYTRBTXKKOG-IYNICTALSA-M
FDA UNII
3M8608UQ61

Pravastatin
An antilipemic fungal metabolite isolated from cultures of Nocardia autotrophica. It acts as a competitive inhibitor of HMG CoA reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES).
1 2D Structure

Pravastatin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
2.1.2 InChI
InChI=1S/C23H36O7.Na/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28;/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28);/q;+1/p-1/t13-,14-,16+,17+,18+,19-,20-,22-;/m0./s1
2.1.3 InChI Key
VWBQYTRBTXKKOG-IYNICTALSA-M
2.1.4 Canonical SMILES
CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)[O-])O)O)O.[Na+]
2.1.5 Isomeric SMILES
CC[C@H](C)C(=O)O[C@H]1C[C@@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)O.[Na+]
2.2 Other Identifiers
2.2.1 UNII
3M8608UQ61
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo Pravastatin

2. Apo-pravastatin

3. Bristacol

4. Cs 514

5. Cs-514

6. Cs514

7. Elisor

8. Eptastatin

9. Lin Pravastatin

10. Lin-pravastatin

11. Lipemol

12. Liplat

13. Lipostat

14. Mevalotin

15. Nu Pravastatin

16. Nu-pravastatin

17. Prareduct

18. Pravachol

19. Pravacol

20. Pravasin

21. Pravastatin

22. Pravastatin Monosodium Salt, (6 Beta)-isomer

23. Pravastatin Sodium Salt

24. Pravastatin Tert Octylamine Salt

25. Pravastatin Tert-octylamine Salt

26. Pravastatin, (6 Beta)-isomer

27. Rms 431

28. Rms-431

29. Rms431

30. Selektine

31. Sodium Salt, Pravastatin

32. Sq 31,000

33. Sq 31000

34. Sq-31,000

35. Sq-31000

36. Sq31,000

37. Sq31000

38. Vasten

2.3.2 Depositor-Supplied Synonyms

1. 81131-70-6

2. Pravachol

3. Mevalotin

4. Selektine

5. Elisor

6. Pravaselect

7. Lipostat

8. Eptastatin Sodium

9. Cs-514

10. Pravastatin Sodium Salt

11. Pravastatin (sodium)

12. Dehypotin Protect

13. Sq-31000

14. Sq-31,000

15. Chebi:8361

16. Bristacol

17. Lipemol

18. Prareduct

19. Pravacol

20. Pravasin

21. 3m8608uq61

22. Nsc-759253

23. Sodium;(3r,5r)-7-[(1s,2s,6s,8s,8ar)-6-hydroxy-2-methyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

24. Aplactin

25. Lipidal

26. Liprevil

27. Pralidon

28. Pravasine

29. Sanaprav

30. Selipran

31. Vasen

32. Epastatin Sodium

33. Dsstox_cid_27525

34. Dsstox_rid_82395

35. Dsstox_gsid_47525

36. Liplat

37. Vasten

38. Pravastatin, Sodium Salt

39. (3r,5r)-3,5-dihydroxy-7-((1s,2s,6s,8s,8ar)-6-hydroxy-2-methyl-8-(((s)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic Acid, Sodium Salt

40. Cas-81131-70-6

41. Pravastatin Natrium Mayrho Fer

42. Sq 31000

43. 3-beta-hydroxycompactin Sodium Salt

44. Drg-0319

45. Chembl690

46. Unii-3m8608uq61

47. Cres Pravastatin

48. Pravachol (tn)

49. Ncgc00095183-01

50. Pravastatin Sodium [usan:usp:jan]

51. Mfcd00887601

52. Pravastatinsodium,(s)

53. Cs-514 Sodium

54. Pravastatin Sodium- Bio-x

55. Schembl3013

56. Sodium (+)-(betar,deltar,1s,2s,6s,8s,8ar)-1,2,6,7,8,8a-hexahydro-beta,delta,6,8-tetrahydroxy-2-methyl-1-naphthaleneheptanoate, 8-((2s)-2-methylbutyrate)

57. Pravastatin Sodium [mi]

58. Dtxsid6047525

59. Pravastatin Sodium [jan]

60. Hy-b0165a

61. Pravastatin Sodium (jp17/usp)

62. Pravastatin Sodium [usan]

63. Hms2051p05

64. Hms3268l20

65. Hms3413e20

66. Pravastatin Sodium [vandf]

67. Hexahydronaphthalen-1-yl)heptanoate

68. Pravastatin Sodium [mart.]

69. Amy40517

70. Pravastatin Sodium [usp-rs]

71. Pravastatin Sodium [who-dd]

72. Tox21_111474

73. Tox21_300270

74. S3036

75. Akos015896504

76. Akos015964902

77. Ccg-100926

78. Cs-2003

79. Nc00176

80. Nsc 759253

81. Pravastatin Sodium [orange Book]

82. Ncgc00092370-01

83. Ncgc00254232-01

84. Pravastatin Sodium [ep Monograph]

85. 1-naphthaleneheptanoic Acid, 1,2,6,7,8,8a-hexahydro-2-methyl-8-(2-methyl-1-oxobutoxy)-beta,delta,6-trihydroxy-, Monosodium Salt, (1s-(1-alpha(beta-s*,delta-s*),2-alpha,6-alpha,8-beta(r*),8a-alpha))-

86. 1-naphthaleneheptanoic Acid, 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, Monosodium Salt, (1s-(1alpha(betas*,deltas*),2alpha,6alpha,8beta(r*),8aalpha))-

87. Bp164292

88. Pravastatin Sodium [usp Monograph]

89. P1796

90. D00893

91. Pravigard Pac Component Pravastatin Sodium

92. Pravastatin Sodium Component Of Pravigard Pac

93. Q27108059

94. Pravastatin Sodium Salt Hydrate, >=98% (hplc), Powder

95. 2-methyl-8-((s)-2-methylbutanoyloxy)-1,2,6,7,8,8a-

96. Sodium (3r,5r)-3,5-dihydroxy-7-((1s,2s,6s,8s,8ar)-6-hydroxy-

97. (?r,?r,1s,2s,6s,8s,8ar)-1,2,6,7,8,8a-hexahydro-?,?,6-trihydroxy-2-methyl-8-[(2s)-2-methyl-1-oxobutoxy]-1-naphthaleneheptanoic Acid Monosodium Salt

98. (3r,5r)-3,5-dihydroxy-7-((1s,2s,6s,8s,8ar)-6-hydroxy-2-methyl-8-(((s)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoicacid,sodiumsalt

99. 1-naphthaleneheptanoic Acid, 1,2,6,7,8,8a-hexahydro-.beta.,d,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, Monosodium Salt, (1s-(1.alpha.(.beta.s*,ds*),2.alpha.,6.alpha.,8.beta.(r*),8a.alpha.))-

100. Sodium (+)-(.beta.r,dr,1s,2s,6s,8s,8ar)-1,2,6,7,8,8a-hexahydro-.beta.,d,6,8-tetrahydroxy-2-methyl-1-naphthaleneheptanoate, 8-((2s)-2-methylbutyrate)

101. Sodium (3r,5r)-3,5-dihydroxy-7-((1s,2s,6s,8s,8ar)-6-hydroxy-2-methyl-8-((s)-2-methylbutanoyloxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoate

102. Sodium (3r,5r)-3,5-dihydroxy-7-[(1s,2s,6s,8s,8ar)-6-hydroxy-2-methyl-8-{[(2s)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoate

2.4 Create Date
2007-11-09
3 Chemical and Physical Properties
Molecular Weight 446.5 g/mol
Molecular Formula C23H35NaO7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count11
Exact Mass446.22804773 g/mol
Monoisotopic Mass446.22804773 g/mol
Topological Polar Surface Area127 Ų
Heavy Atom Count31
Formal Charge0
Complexity662
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NamePravachol
PubMed HealthPravastatin (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelPRAVACHOL (pravastatin sodium) is one of a class of lipid-lowering compounds, the statins, which reduce cholesterol biosynthesis. These agents are competitive inhibitors of HMG-CoA reductase, the enzyme catalyzing the early rate-limiting step in ch...
Active IngredientPravastatin sodium
Dosage FormTablet
RouteOral
Strength10mg; 80mg; 40mg; 20mg
Market StatusPrescription
CompanyBristol Myers Squibb

2 of 4  
Drug NamePravastatin sodium
Drug LabelPravastatin sodium tablets are one of a class of lipid-lowering compounds, the HMG-CoA reductase inhibitors, which reduce cholesterol biosynthesis. These agents are competitive inhibitors of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase,...
Active IngredientPravastatin sodium
Dosage FormTablet
Routeoral; Oral
Strength10mg; 80mg; 40mg; 20mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Teva; Lupin Pharms; Apotex; Sandoz; Cipla; Watson Labs; Glenmark Generics; Teva Pharms; Pliva Hrvatska Doo; Zydus Pharms Usa; Dr Reddys Labs; Mylan

3 of 4  
Drug NamePravachol
PubMed HealthPravastatin (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelPRAVACHOL (pravastatin sodium) is one of a class of lipid-lowering compounds, the statins, which reduce cholesterol biosynthesis. These agents are competitive inhibitors of HMG-CoA reductase, the enzyme catalyzing the early rate-limiting step in ch...
Active IngredientPravastatin sodium
Dosage FormTablet
RouteOral
Strength10mg; 80mg; 40mg; 20mg
Market StatusPrescription
CompanyBristol Myers Squibb

4 of 4  
Drug NamePravastatin sodium
Drug LabelPravastatin sodium tablets are one of a class of lipid-lowering compounds, the HMG-CoA reductase inhibitors, which reduce cholesterol biosynthesis. These agents are competitive inhibitors of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase,...
Active IngredientPravastatin sodium
Dosage FormTablet
Routeoral; Oral
Strength10mg; 80mg; 40mg; 20mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Teva; Lupin Pharms; Apotex; Sandoz; Cipla; Watson Labs; Glenmark Generics; Teva Pharms; Pliva Hrvatska Doo; Zydus Pharms Usa; Dr Reddys Labs; Mylan

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anticholesteremic Agents

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Hydroxymethylglutaryl-CoA Reductase Inhibitors [MoA]; HMG-CoA Reductase Inhibitor [EPC]

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22-Jan-2021
19-Sep-2024
KGS
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DOSAGE - TABLET;ORAL - 10MG **Federal Registe...DOSAGE - TABLET;ORAL - 10MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19898

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DOSAGE - TABLET;ORAL - 20MG **Federal Registe...DOSAGE - TABLET;ORAL - 20MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19898

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DOSAGE - TABLET;ORAL - 40MG **Federal Registe...DOSAGE - TABLET;ORAL - 40MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19898

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DOSAGE - TABLET;ORAL - 80MG **Federal Registe...DOSAGE - TABLET;ORAL - 80MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19898

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