Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1445)
Drug Name
Rosuvastatin
Synonyms
Rosuvastatin; Rosuvastatin calcium; ZD-4522; (3R,5R)-Rosuvastatin; Creston (TN); (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid; (3R,5S,E)-7-(4-(4-Fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoic acid; (E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid; 287714-41-4; 413KH5ZJ73; CHEBI:38545; CHEMBL1496; UNII-413KH5ZJ73
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Structure
3D MOL 2D MOL
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
Cross-matching ID
PubChem CID
446157
PubChem SID
822168 ; 10299840 ; 14810118 ; 14834808 ; 24775831 ; 26612833 ; 26680899 ; 36888655 ; 46509022 ; 46518448 ; 47960010 ; 48035409 ; 50070881 ; 50122666 ; 53790555 ; 57404725 ; 80442666 ; 88531873 ; 92124833 ; 96025178 ; 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
ChEBI ID
ChEBI:38545
CAS Number
287714-41-4
TTD Drug ID
D0JE2E
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
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
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
N-Desmethylrosuvastatin DM016565
124653453
Oxidation - N-demethylation 1 [4] , [6]
Rosuvastatin 5S-lactone DM016763
154699802
Oxidation - N-dealkylation 1 [4] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009592 Rosuvastatin N-Desmethylrosuvastatin Oxidation - N-demethylation CYP2C9 ... [4], [6]
MR009593 Rosuvastatin Rosuvastatin 5S-lactone Oxidation - N-dealkylation CYP2C9 [4], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
⏷ Show the Full List of 6  DME(s)
References
1 Aspirin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetics of rosuvastatin when coadministered with rifampicin in healthy males: a randomized, single-blind, placebo-controlled, crossover study. Clin Ther. 2008 Jul;30(7):1283-9.
3 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.
4 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.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Simultaneous Determination of Rosuvastatin, Rosuvastatin-5?S-lactone, and N-desmethyl Rosuvastatin in Human Plasma by UPLC-MS/MS and Its Application to Clinical Study

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