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

General Information of Drug (ID: DR0738)
Drug Name
Fluvastatin sodium
Synonyms
Fluindostatin sodium; Fluvastatin (sodium); Fluvastatin sodium (Lescol); Fluvastatin sodium salt; Fluyastatin Sodium Salt; Fractal; Lescol XL; Lipaxan; Lochol; Prestwick_1032; Sri 62320; Sri-62320; Vastin; XU 62-320; XU-62-320; Xilep XL; 93957-55-2; 94061-80-0; AB01274723-01; C24H25FNNaO4; CAS-93957-55-2; CHEBI:77602; Canef; DSSTox_CID_24758; DSSTox_GSID_44758; DSSTox_RID_80451; Locol; SMR000550480; Sodium (3R,5S,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-3,5-dihydroxyhept-6-enoate; FLUVASTATIN SODIUM; Fluvastatin [INN:BAN]; XU 62320; XU-62320; fluvastatin; (+)-(3R,5S)-fluvastatin; (3R,5S)-fluvastatin; (3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (3R,5S,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; 93957-54-1; C24H26FNO4; CHEBI:38565; EN300-51915; CHEMBL1078
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 433.4 Topological Polar Surface Area 85.5
Heavy Atom Count 31 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
23663976
ChEBI ID
CHEBI:77602
CAS Number
94061-80-0
TTD Drug ID
D08GHB
Formula
C24H25FNNaO4
Canonical SMILES
CC(C)N1C2=CC=CC=C2C(=C1C=CC(CC(CC(=O)[O-])O)O)C3=CC=C(C=C3)F.[Na+]
InChI
1S/C24H26FNO4.Na/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30;/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30);/q;+1/p-1/b12-11+;/t18-,19-;/m1./s1
InChIKey
ZGGHKIMDNBDHJB-NRFPMOEYSA-M
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
5-hydroxyfluvastatin DM002034 N. A. Oxidation - 5-Hydroxylation 1 [8] , [9]
5-OH-fluvastatin DM002036 N. A. Oxidation - Hydroxylation 1 [8] , [10] , [11]
6-hydroxyfluvastatin DM002032
10455210
Oxidation - 6-Hydroxylation 1 [12]
6-OH-fluvastatin DM002035 N. A. Oxidation - Hydroxylation 1 [8] , [10] , [11]
N-Deisopropyl-fluvastatin DM002033 N. A. Oxidation - N-Deisopropylation 1 [8] , [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001061 Fluvastatin sodium 6-hydroxyfluvastatin Oxidation - 6-Hydroxylation CYP2C9 [12]
MR001062 Fluvastatin sodium N-Deisopropyl-fluvastatin Oxidation - N-Deisopropylation Unclear [8], [9]
MR001063 Fluvastatin sodium 5-hydroxyfluvastatin Oxidation - 5-Hydroxylation CYP1A1 ... [8], [9]
MR001064 Fluvastatin sodium 6-OH-fluvastatin Oxidation - Hydroxylation CYP2C9 [8], [10], [11]
MR001065 Fluvastatin sodium 5-OH-fluvastatin Oxidation - Hydroxylation CYP3A4 ... [8], [10], [11]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 6  DME(s)
References
1 Fluvastatin Sodium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Regulation of cytochrome P450 expression by inhibitors of hydroxymethylglutaryl-coenzyme A reductase in primary cultured rat hepatocytes and in rat liver. Drug Metab Dispos. 1996 Nov;24(11):1197-204.
3 Comparison of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors (statins) as inhibitors of cytochrome P450 2C8. Basic Clin Pharmacol Toxicol. 2005 Aug;97(2):104-8.
4 Limitations of S-warfarin truncated area under the concentration-time curve to predict cytochrome P450 2c9 activity. Drug Metab Lett. 2012 Jun 1;6(2):94-101.
5 Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81.
6 Effects of fluvastatin on the pharmacokinetics of eepaglinide: possible role of CYP3A4 and P-glycoprotein inhibition by fluvastatin. Korean J Physiol Pharmacol. 2013 Jun;17(3):245-51.
7 Lipid-lowering response to statins is affected by CYP3A5 polymorphism. Pharmacogenetics. 2004 Aug;14(8):523-5.
8 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.
9 Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32.
10 Metabolism and transport of oxazaphosphorines and the clinical implications Drug Metab Rev. 2005;37(4):611-703. doi: 10.1080/03602530500364023.
11 Assessment of ifosfamide pharmacokinetics, toxicity, and relation to CYP3A4 activity as measured by the erythromycin breath test in patients with sarcoma Cancer. 2007 Jun 1;109(11):2315-22. doi: 10.1002/cncr.22669.
12 Diagnosis and subclassification of follicle center and mantle cell lymphomas on fine-needle aspirates: A cytologic and immunocytochemical approach based on the Revised European-American Lymphoma (REAL) classification Cancer. 1999 Aug 25;87(4):216-23.

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