Drug Information

General Information
Drug ID
DR00223
Drug Name
Rosuvastatin
Synonyms
(3R,5S,6E)-7-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoic acid; (3R,5S,6E)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid; (3R,5S,6E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid; (E,3R,5R)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-ylpyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid; (E,3R,5S)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-ylpyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid; (S-((R*,S*-(E)))-7-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl) amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoic acid, calcium salt (2:1); (S-(R*,S*-(E)))-7-(4-(4-Fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoic acid, calcium salt (2:1); 6-Heptenoic acid, 7-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-, (3R,5S,6E); 6-Heptenoic acid, 7-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-, calcium salt (2:1), (3R,5S,6E); AZD-4522; Astende; Bis[(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino] pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhelpt-6-enoic acid] calcium salt; Calcium (E,3R,5S)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-ylpyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate; Cirantan; Cresadex; Creston; Creston (TN);Crestor (TN); Crestor; Provisacor; Pyrimidine Compound, 26; Razel; Rosedex; Rosimol; Rosumed; Rosustatin; Rosuvas; Rosuvast; Rosuvastatin (INN); Rosuvastatin [INN]; Rosuvastatin calcium; Rosuvastatin calcium (JAN/USAN); Rosuvastatin calcium [USAN]; Rosuvastatin hemicalcium; Rosvel; Rovartal; S 4522; S-4522; Simestat; Sinlip; Vivacor; ZD 4522; ZD 4522, calcium salt; ZD-4522; ZD4522
Drug Type
Small molecular drug
Indication Hypercholesterolemia [ICD11:5C80.0] Approved [1]
Therapeutic Class
Anticholesteremic Agents
Structure
3D MOL 2D MOL
Formula
C22H28FN3O6S
Canonical SMILES
CC(C)C1=NC(=NC(=C1C=CC(CC(CC(=O)O)O)O)C2=CC=C(C=C2)F)N(C)S(=O)(=O)C
InChI
InChI=1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1
InChIKey
BPRHUIZQVSMCRT-VEUZHWNKSA-N
CAS Number
CAS 287714-41-4
Pharmaceutical Properties Molecular Weight 481.5 Topological Polar Surface Area 149
Heavy Atom Count 33 Rotatable Bond Count 10
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 10
XLogP
1.6
PubChem CID
446157
PubChem SID
10299840 ,103556348 ,104635880 ,104829200 ,124637938 ,126680774 ,126731182 ,127315738 ,127315739 ,127315740 ,127315741 ,127315742 ,127315743 ,127315744 ,127315745 ,127315746 ,127315747 ,127315748 ,127315749 ,127315750 ,127315751 ,127315752 ,127315753 ,127315754 ,127315755 ,127315756 ,127315757 ,127315758 ,135084331 ,135650928 ,135723476 ,14810118 ,14834808 ,24775831 ,26612833 ,26680899 ,36888655 ,46509022 ,46518448 ,47960010 ,48035409 ,50070881 ,50122666 ,53790555 ,57404725 ,80442666 ,822168 ,88531873 ,92124833 ,96025178
ChEBI ID
ChEBI:38545
TTD Drug ID
D0JE2E
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [2]
NTCP Transporter Info Sodium/taurocholate cotransporting polypeptide Substrate [3]
OAT3 Transporter Info Organic anion transporter 3 Substrate [4]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [3]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [2]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [2]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [2]
P-GP Transporter Info P-glycoprotein 1 Substrate [2]
Drug-Transporter Activity Data
Drug-Transporter Activity Data BCRP Transporter Info Km =2.02 microM Human embryonic kidney cells (HEK293)-BCRP [2]
BCRP Transporter Info Km =10.1 microM Madin-Darby canine kidney cells (MDCKII)-BCRP [5]
NTCP Transporter Info Km =65 microM Human cervical cancer cell line (Hela)-NTCP [3]
OAT3 Transporter Info Km =7.4 microM Oocytes-OAT3 [4]
OATP1A2 Transporter Info Km =2.6 microM Human cervical cancer cell line (Hela)-OATP1A2 [3]
OATP1B1 Transporter Info Km =4 microM Human cervical cancer cell line (Hela)-OATP1B1 [3]
OATP1B1 Transporter Info Km =7.3 microM Human cervical cancer cell line (Hela)-OATP1B1 [3]
OATP1B1 Transporter Info Km =0.8 microM Human embryonic kidney cells (HEK293)-OATP1B1 [2]
OATP1B1 Transporter Info Km =8.5 microM Oocytes-OATP1B1 [6]
OATP1B3 Transporter Info Km =9.8 microM Human cervical cancer cell line (Hela)-OATP1B3 [3]
OATP1B3 Transporter Info Km =14.2 microM Human embryonic kidney cells (HEK293)-OATP1B3 [2]
OATP2B1 Transporter Info Km =2.4 microM Human cervical cancer cell line (Hela)-OATP2B1 [3]
OATP2B1 Transporter Info Km =6.42 microM Human embryonic kidney cells (HEK293)-OATP2B1 [2]
References
1 Rosuvastatin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Involvement of multiple transporters in the hepatobiliary transport of rosuvastatin. Drug Metab Dispos. 2008 Oct;36(10):2014-23.
3 Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics. Gastroenterology. 2006 May;130(6):1793-806.
4 The contribution of organic anion transporters OAT1 and OAT3 to the renal uptake of rosuvastatin. J Pharmacol Exp Ther. 2007 Sep;322(3):1221-7.
5 Effect of silymarin supplement on the pharmacokinetics of rosuvastatin. Pharm Res. 2008 Aug;25(8):1807-14.
6 Rosuvastatin pharmacokinetics in heart transplant recipients administered an antirejection regimen including cyclosporine. Clin Pharmacol Ther. 2004 Aug;76(2):167-77.

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