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Chemistry

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Also known as: 134523-00-5, Cardyl, Lipitor, 110862-48-1, Torvast, Atorvastatin calcium
Molecular Formula
C33H35FN2O5
Molecular Weight
558.6  g/mol
InChI Key
XUKUURHRXDUEBC-KAYWLYCHSA-N
FDA UNII
A0JWA85V8F

Atorvastatin
A pyrrole and heptanoic acid derivative, HYDROXYMETHYLGLUTARYL-COA REDUCTASE INHIBITOR (statin), and ANTICHOLESTEREMIC AGENT that is used to reduce serum levels of LDL-CHOLESTEROL; APOLIPOPROTEIN B; and TRIGLYCERIDES. It is used to increase serum levels of HDL-CHOLESTEROL in the treatment of HYPERLIPIDEMIAS, and for the prevention of CARDIOVASCULAR DISEASES in patients with multiple risk factors.
Atorvastatin is a HMG-CoA Reductase Inhibitor. The mechanism of action of atorvastatin is as a Hydroxymethylglutaryl-CoA Reductase Inhibitor.
1 2D Structure

Atorvastatin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
2.1.2 InChI
InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1
2.1.3 InChI Key
XUKUURHRXDUEBC-KAYWLYCHSA-N
2.1.4 Canonical SMILES
CC(C)C1=C(C(=C(N1CCC(CC(CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
2.1.5 Isomeric SMILES
CC(C)C1=C(C(=C(N1CC[C@H](C[C@H](CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
2.2 Other Identifiers
2.2.1 UNII
A0JWA85V8F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (3r,5r)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1h-pyrrol-1-yl)-3,5-dihydroxyheptanoic Acid

2. Atorvastatin Calcium

3. Atorvastatin Calcium Anhydrous

4. Atorvastatin Calcium Hydrate

5. Atorvastatin Calcium Trihydrate

6. Atorvastatin, Calcium Salt

7. Ci 981

8. Ci-981

9. Ci981

10. Lipitor

11. Liptonorm

2.3.2 Depositor-Supplied Synonyms

1. 134523-00-5

2. Cardyl

3. Lipitor

4. 110862-48-1

5. Torvast

6. Atorvastatin Calcium

7. Rel-atorvastatin

8. (3r,5r)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1h-pyrrol-1-yl)-3,5-dihydroxyheptanoic Acid

9. Atorvastatin (inn)

10. Ci 981

11. Lipitor (tn)

12. Tozalip

13. Xavator

14. (3r,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic Acid

15. A0jwa85v8f

16. Chembl1487

17. (r-(r*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1h-pyrrole-1-heptanoic Acid

18. Chebi:39548

19. (3r,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1h-pyrrol-1-yl]-3,5-dihydroxyheptanoic Acid

20. 134523-03-8

21. Atorvastatin [inn]

22. Atorvastatin [inn:ban]

23. 1h-pyrrole-1-heptanoic Acid, 2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-, (r-(r*,r*))-

24. 7-[2-(4-fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]- 3,5-dihydroxy-heptanoic Acid

25. Atorvastatin Calcium Salt

26. Atorvastatina

27. Atorvastatine

28. Atrovastin

29. Atofast

30. Atorcor

31. Atorlip

32. Lipilou

33. Lipinon

34. Atorin

35. Ator

36. Lipitor(tm)

37. (3r,5r)-7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-(phenylcarbamoyl)-1h-pyrrol-1-yl]-3,5-dihydroxyheptanoic Acid

38. (3r,5r)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxy-heptanoic Acid

39. (3r,5r)-7-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1h-pyrrol-1-yl]-3,5-dihydroxyheptanoic Acid

40. Sortis (tn)

41. Ccris 7159

42. Hsdb 7039

43. Ncgc00159458-03

44. Unii-a0jwa85v8f

45. Atorvastatinum

46. (betar,deltar)-2-(p-fluorophenyl)-beta,delta-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoic Acid

47. Atorvastatin & Primycin

48. Atorvastatin [mi]

49. Dsstox_cid_9868

50. Atorvastatin [hsdb]

51. Schembl3831

52. Atorvastatin [vandf]

53. Dsstox_rid_78825

54. Dsstox_gsid_29868

55. Atorvastatin [who-dd]

56. Bidd:gt0336

57. Atorvastatin (relative Stereo)

58. Gtpl2949

59. Dtxsid8029868

60. Bdbm22164

61. Dtxsid60274003

62. Hms3715l05

63. Hms3886c20

64. Lipilou; Tozalip; Torvast; Cardyl

65. (3s,5s)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic Acid

66. Act03225

67. Hy-b0589

68. Zinc3920719

69. Tox21_302417

70. Mfcd00899261

71. S5715

72. Akos000281127

73. Ac-9386

74. Ccg-221172

75. Db01076

76. Mrf-0000761

77. Ncgc00159458-02

78. Ncgc00159458-20

79. Ncgc00255181-01

80. (3r,5r)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic Acid

81. 1h-pyrrole-1-heptanoic Acid, 2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-, (betar,deltar)-

82. 7-[2-(4-fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic Acid

83. As-35260

84. Cas-134523-00-5

85. C06834

86. D07474

87. 523a005

88. A802259

89. A806791

90. A806793

91. Q668093

92. Sr-01000872702

93. Sr-01000872702-1

94. Brd-k69726342-001-02-6

95. Atorvastatin Is Known As An Hmg-coa Reductase Inhibitor.

96. (.beta.r,.delta.r)-2-(p-fluorophenyl)-.beta.,.delta.-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoic Acid

97. (3r,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-yl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic Acid

98. (3r,5r)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic Acid

99. (3r,5r)-7-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-4-phenyl-2-(propan-2-yl)-1h-pyrrol-1-yl]-3,5-dihydroxyheptanoic Acid

100. 1h-pyrrole-1-heptanoic Acid, 2-(4-fluorophenyl)-.beta.,.delta.-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-, (r-(r*,r*))-

101. Sodium 7-[5-(4-fluorophenyl)-2-isopropyl-4-phenyl-3-(phenylcarbamoyl)-2,3-dihydropyrrol-1-yl]-3,5-dihydroxy-heptanoate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 558.6 g/mol
Molecular Formula C33H35FN2O5
XLogP35
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count12
Exact Mass558.25300038 g/mol
Monoisotopic Mass558.25300038 g/mol
Topological Polar Surface Area112 Ų
Heavy Atom Count41
Formal Charge0
Complexity822
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameLipitor
PubMed HealthAtorvastatin (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelLIPITOR (atorvastatin calcium) is a synthetic lipid-lowering agent. Atorvastatin is an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase. This enzyme catalyzes the conversion of HMG-CoA to mevalonate, an early and rate-limiting...
Active IngredientAtorvastatin calcium
Dosage FormTablet
RouteOral
Strengtheq 20mg base; eq 40mg base; eq 80mg base; eq 10mg base
Market StatusPrescription
CompanyPfizer

2 of 2  
Drug NameLipitor
PubMed HealthAtorvastatin (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelLIPITOR (atorvastatin calcium) is a synthetic lipid-lowering agent. Atorvastatin is an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase. This enzyme catalyzes the conversion of HMG-CoA to mevalonate, an early and rate-limiting...
Active IngredientAtorvastatin calcium
Dosage FormTablet
RouteOral
Strengtheq 20mg base; eq 40mg base; eq 80mg base; eq 10mg base
Market StatusPrescription
CompanyPfizer

4.2 Therapeutic Uses

Anticholesteremic Agents; Hydroxymethylglutaryl-CoA Reductase Inhibitors

National Library of Medicine's Medical Subject Headings. Atorvastatin. Online file (MeSH, 2016). Available from, as of October 28, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html


In adult patients without clinically evident coronary heart disease, but with multiple risk factors for coronary heart disease such as age, smoking, hypertension, low HDL-C, or a family history of early coronary heart disease, Lipitor is indicated to: Reduce the risk of myocardial infarction; Reduce the risk of stroke; Reduce the risk for revascularization procedures and angina. /Included in US product label/

NIH; DailyMed. Current Medication Information for Lipitor (Atorvastatin Calcium) Tablet, Film-coated (Updated: November 2015). Available from, as of October 28, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6e131fe-e7df-4876-83f7-9156fc4e8228


In patients with type 2 diabetes, and without clinically evident coronary heart disease, but with multiple risk factors for coronary heart disease such as retinopathy, albuminuria, smoking, or hypertension, Lipitor is indicated to: Reduce the risk of myocardial infarction; Reduce the risk of stroke. /Included in US product label/

NIH; DailyMed. Current Medication Information for Lipitor (Atorvastatin Calcium) Tablet, Film-coated (Updated: November 2015). Available from, as of October 28, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6e131fe-e7df-4876-83f7-9156fc4e8228


In patients with clinically evident coronary heart disease, Lipitor is indicated to: Reduce the risk of non-fatal myocardial infarction; Reduce the risk of fatal and non-fatal stroke; Reduce the risk for revascularization procedures; Reduce the risk of hospitalization for congestive heart failure (CHF); Reduce the risk of angina. /Included in US product label/

NIH; DailyMed. Current Medication Information for Lipitor (Atorvastatin Calcium) Tablet, Film-coated (Updated: November 2015). Available from, as of October 28, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6e131fe-e7df-4876-83f7-9156fc4e8228


For more Therapeutic Uses (Complete) data for ATORVASTATIN (15 total), please visit the HSDB record page.


4.3 Drug Warning

Lipitor is contraindicated in women who are or may become pregnant. Serum cholesterol and triglycerides increase during normal pregnancy. Lipid lowering drugs offer no benefit during pregnancy because cholesterol and cholesterol derivatives are needed for normal fetal development. Atherosclerosis is a chronic process, and discontinuation of lipid-lowering drugs during pregnancy should have little impact on long-term outcomes of primary hypercholesterolemia therapy.

NIH; DailyMed. Current Medication Information for Lipitor (Atorvastatin Calcium) Tablet, Film-coated (Updated: November 2015). Available from, as of October 28, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6e131fe-e7df-4876-83f7-9156fc4e8228


Statins may cause fetal harm when administered to a pregnant woman. Lipitor should be administered to women of childbearing potential only when such patients are highly unlikely to conceive and have been informed of the potential hazards. If the woman becomes pregnant while taking Lipitor, it should be discontinued immediately and the patient advised again as to the potential hazards to the fetus and the lack of known clinical benefit with continued use during pregnancy.

NIH; DailyMed. Current Medication Information for Lipitor (Atorvastatin Calcium) Tablet, Film-coated (Updated: November 2015). Available from, as of October 28, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6e131fe-e7df-4876-83f7-9156fc4e8228


It is not known whether atorvastatin is excreted in human milk, but a small amount of another drug in this class does pass into breast milk. Nursing rat pups had plasma and liver drug levels of 50% and 40%, respectively, of that in their mother's milk. Animal breast milk drug levels may not accurately reflect human breast milk levels. Because another drug in this class passes into human milk and because statins have a potential to cause serious adverse reactions in nursing infants, women requiring Lipitor treatment should be advised not to nurse their infants.

NIH; DailyMed. Current Medication Information for Lipitor (Atorvastatin Calcium) Tablet, Film-coated (Updated: November 2015). Available from, as of October 28, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6e131fe-e7df-4876-83f7-9156fc4e8228


Myopathy (defined as muscle aches or weakness in conjunction with increases in creatine kinase [CK, creatine phosphokinase, CPK] concentrations exceeding 10 times the upper limit of normal [ULN]) has been reported occasionally in patients receiving statins, including atorvastatin. Rhabdomyolysis with acute renal failure secondary to myoglobinuria also has been reported rarely in patients receiving statins, including atorvastatin.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1844


For more Drug Warnings (Complete) data for ATORVASTATIN (33 total), please visit the HSDB record page.


4.4 Drug Indication

Atorvastatin is indicated for the treatment of several types of dyslipidemias, including primary hyperlipidemia and mixed dyslipidemia in adults, hypertriglyceridemia, primary dysbetalipoproteinemia, homozygous familial hypercholesterolemia, and heterozygous familial hypercholesterolemia in adolescent patients with failed dietary modifications. Dyslipidemia describes an elevation of plasma cholesterol, triglycerides or both as well as to the presence of low levels of high-density lipoprotein. This condition represents an increased risk for the development of atherosclerosis. Atorvastatin is indicated, in combination with dietary modifications, to prevent cardiovascular events in patients with cardiac risk factors and/or abnormal lipid profiles. Atorvastatin can be used as a preventive agent for myocardial infarction, stroke, revascularization, and angina, in patients without coronary heart disease but with multiple risk factors and in patients with type 2 diabetes without coronary heart disease but multiple risk factors. Atorvastatin may be used as a preventive agent for non-fatal myocardial infarction, fatal and non-fatal stroke, revascularization procedures, hospitalization for congestive heart failure and angina in patients with coronary heart disease. Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD. Statin-indicated conditions include diabetes mellitus, clinical atherosclerosis (including myocardial infarction, acute coronary syndromes, stable angina, documented coronary artery disease, stroke, trans ischemic attack (TIA), documented carotid disease, peripheral artery disease, and claudication), abd