Drug Information

General Information
Drug ID
DR00030
Drug Name
Atorvastatin
Synonyms
(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid; (3R,5R)-7-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-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; (betaR,deltaR)-2-(p-Fluorophenyl)-beta,delta-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoic acid; 7-[2-(4-FLUORO-PHENYL)-5-ISOPROPYL-3-PHENYL-4-PHENYLCARBAMOYL-PYRROL-1-YL]-3,5-DIHYDROXY-HEPTANOIC ACID; Atogal; Atorlip; Atorpic; Atorvastatin (INN); Atorvastatin [INN:BAN]; Atorvastatina; Atorvastatine; Atorvastatinium; Atrovastin; Cardyl; Faboxim; Lipitor (TN); Lipitor(TM); Lipotropic; Lipovastatinklonal; Liprimar; Lowden; Sincol; Sortis; Sortis (TN); Sotis; Torvacard; Torvast; Totalip; Tozalip; Tulip; Vastina; Xanator; Xarator; Xavator; Zurinel
Drug Type
Small molecular drug
Indication Heart attack [ICD11:BA41.Z] Approved [1]
Dyslipidaemias [ICD11:5C8Z] Approved [1]
Hyperlipidaemia [ICD11:5C8Z] Approved [1]
Therapeutic Class
Anticholesteremic Agents
Structure
3D MOL 2D MOL
Formula
C33H35FN2O5
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
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
InChIKey
XUKUURHRXDUEBC-KAYWLYCHSA-N
CAS Number
CAS 134523-00-5
Pharmaceutical Properties Molecular Weight 558.6 Topological Polar Surface Area 112
Heavy Atom Count 41 Rotatable Bond Count 12
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
XLogP
5
PubChem CID
60823
PubChem SID
103554720 ,104178840 ,104321734 ,104829550 ,117367061 ,124892211 ,126525305 ,126624171 ,126658151 ,126682126 ,127315782 ,127315783 ,127315784 ,127315785 ,127315786 ,127315787 ,127315788 ,127315789 ,127315790 ,127315791 ,127315792 ,127315793 ,14910832 ,26684326 ,26697359 ,29215408 ,43118161 ,49845979 ,50037926 ,51091801 ,53787715 ,56311281 ,56311722 ,56311943 ,56311969 ,56312802 ,56313042 ,56313334 ,56313578 ,56314463 ,57314133 ,75432172 ,7884979 ,7978735 ,8187078 ,822166 ,85856289 ,9052 ,92714388 ,93166494
ChEBI ID
ChEBI:39548
TTD Drug ID
D01QIN
DT(s) Transporting This Drug ABCG1 Transporter Info ATP-binding cassette sub-family G member 1 Substrate [2]
MCT1 Transporter Info Monocarboxylate transporter 1 Substrate [3]
MCT2 Transporter Info Monocarboxylate transporter 2 Substrate [4]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [5]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [6]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [7]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [8]
P-GP Transporter Info P-glycoprotein 1 Substrate [9]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OATP1B1 Transporter Info Km =0.77 microM Human embryonic kidney cells (HEK293)-OATP1B1 [10]
OATP1B1 Transporter Info Km =12.4 microM Human embryonic kidney cells (HEK293)-OATP1B1 [11]
OATP1B1 Transporter Info Km =18.9 microM Human embryonic kidney cells (HEK293)-OATP1B1 [12]
OATP1B3 Transporter Info Km =0.73 microM Human embryonic kidney cells (HEK293)-OATP1B3 [10]
OATP2B1 Transporter Info Km =2.84 microM Human embryonic kidney cells (HEK293)-OATP2B1 [10]
OATP2B1 Transporter Info Km =0.2 microM Madin-Darby canine kidney cells (MDCKII)-OATP2B1 [13]
References
1 Ramipril was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 HMG-CoA reductase inhibitors, simvastatin and atorvastatin, downregulate ABCG1-mediated cholesterol efflux in human macrophages. J Cardiovasc Pharmacol. 2013 Jul;62(1):90-8.
3 H+-coupled nutrient, micronutrient and drug transporters in the mammalian small intestine. Exp Physiol. 2007 Jul;92(4):603-19.
4 Monocarboxylate Transporters in Drug Disposition: Role in the Toxicokinetics and Toxicodynamics of the Drug of Abuse GHB.
5 Influence of the flavonoids apigenin, kaempferol, and quercetin on the function of organic anion transporting polypeptides 1A2 and 2B1. Biochem Pharmacol. 2010 Dec 1;80(11):1746-53.
6 Rifampicin alters atorvastatin plasma concentration on the basis of SLCO1B1 521T>C polymorphism. Clin Chim Acta. 2009 Jul;405(1-2):49-52.
7 FDA Drug Development and Drug Interactions
8 Human platelets express organic anion-transporting peptide 2B1, an uptake transporter for atorvastatin. Drug Metab Dispos. 2009 May;37(5):1129-37.
9 Tarascon Pocket Pharmacopoeia 2018 Classic Shirt-Pocket Edition.
10 Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63.
11 Functional characterization of SLCO1B1 (OATP-C) variants, SLCO1B1*5, SLCO1B1*15 and SLCO1B1*15+C1007G, by using transient expression systems of HeLa and HEK293 cells. Pharmacogenet Genomics. 2005 Jul;15(7):513-22.
12 effect of OATP1B transporter inhibition on the pharmacokinetics of atorvastatin in healthy volunteers. Clin Pharmacol Ther. 2007 Feb;81(2):194-204.
13 Organic anion transporting polypeptide 2B1 is a high-affinity transporter for atorvastatin and is expressed in the human heart. Clin Pharmacol Ther. 2006 Dec;80(6):607-20.

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