General Information of Drug (ID: DR0155)
Drug Name
Atorvastatin calcium
Synonyms
Atorvastatin Hemicalcium; Atorvastatin calcium [USAN]; Atorvastatin calcium salt; Atorvastatin hemicalcium salt; Atorvastatin; Atorvastatin [INN:BAN]; C33H35FN2O5; CCRIS 7159; CHEBI:39548; CHEMBL1487; Cardyl; HSDB 7039; Lipitor (TN); Sotis; Tozalip; UNII-A0JWA85V8F; Xarator; Xavator; (3R,5R)-7-(2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid; (R-(R*,R*))-2-(4-Fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acid; 110862-48-1; 134523-00-5; A0JWA85V8F; C0GEJ5QCSO; CHEBI:50686; CI 981; CI-981; Calcium (betaR,deltaR)-2-(p-fluorophenyl)-beta,delta-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoate (1:2); DRG-0321; PD 134298-38A; Sortis; Tahor; UNII-C0GEJ5QCSO; YM 548; 134523-03-8
Indication Dyslipidaemia [ICD11: 5C81] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 1155.3 Topological Polar Surface Area 229
Heavy Atom Count 83 Rotatable Bond Count 22
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
60822
ChEBI ID
CHEBI:50686
CAS Number
134523-03-8
TTD Drug ID
D01QIN
Formula
C66H68CaF2N4O10
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.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.[Ca+2]
InChI
1S/2C33H35FN2O5.Ca/c2*1-21(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;/h2*3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40);/q;;+2/p-2/t2*26-,27-;/m11./s1
InChIKey
FQCKMBLVYCEXJB-MNSAWQCASA-L
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2-hydroxyatorvastatin acid DM015527
9808225
Unclear - Unclear 1 [8] , [9]
4-hydroxyatorvastatin acid DM015541
9851106
Unclear - Unclear 1 [8]
Atorvastatin lactone DM015852
13923664
Conjugation - Lactonization 1 [10]
2-hydroxyatorvastatin lactone DM015967
20095616
Unclear - Unclear 2 [10]
2-hydroxyatorvastatin lactone DM015967
20095616
Conjugation - Lactonization 2 [10]
4-hydroxyatorvastatin lactone DM015998
21907652
Unclear - Unclear 2 [10]
4-hydroxyatorvastatin lactone DM015998
21907652
Conjugation - Lactonization 2 [10]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009873 Atorvastatin calcium 2-hydroxyatorvastatin acid Unclear - Unclear CYP3A4 [8], [9]
MR009875 Atorvastatin calcium 4-hydroxyatorvastatin acid Unclear - Unclear CYP3A4 [8]
MR009877 Atorvastatin calcium Atorvastatin lactone Conjugation - Lactonization Unclear [10]
MR009874 2-hydroxyatorvastatin acid 2-hydroxyatorvastatin lactone Conjugation - Lactonization Unclear [10]
MR009876 4-hydroxyatorvastatin acid 4-hydroxyatorvastatin lactone Conjugation - Lactonization Unclear [10]
MR009878 Atorvastatin lactone 2-hydroxyatorvastatin lactone Unclear - Unclear Unclear [10]
MR009879 Atorvastatin lactone 4-hydroxyatorvastatin lactone Unclear - Unclear CYP3A4 [10]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[7]
⏷ Show the Full List of 6  DME(s)
References
1 Atorvastatin Calcium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
4 Effects of acid and lactone forms of eight HMG-CoA reductase inhibitors on CYP-mediated metabolism and MDR1-mediated transport. Pharm Res. 2006 Mar;23(3):506-12.
5 Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers.
6 Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid. Drug Metab Dispos. 2007 Aug;35(8):1315-24.
7 UGT1A1*28 is associated with decreased systemic exposure of atorvastatin lactone. Mol Diagn Ther. 2013 Aug;17(4):233-7.
8 Influence of Drug-Drug Interactions on the Pharmacokinetics of Atorvastatin and Its Major Active Metabolite ortho-OH-Atorvastatin in Aging People Living with HIV
9 Development of an LC-MS/MS method for simultaneous determination of ticagrelor and its active metabolite during concomitant treatment with atorvastatin
10 Rifampin markedly decreases and gemfibrozil increases the plasma concentrations of atorvastatin and its metabolites

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