Drug Information

General Information
Drug ID
DR00124
Drug Name
Fluvastatin
Synonyms
(+)-(3R,5S)-fluvastatin; (-)-(3S,5R)-fluvastatin; (3R,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (3R,5R,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (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; (3R,5S,6E)-rel-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid; (3S,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (3S,5R,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (E,3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (E,3S,5R)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid; (Z,3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid; 7-(3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl)-3,5-dihydroxy-6-heptenoate; 7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid; Canef; Canef(TN); Cranoc; Fluindostatin; Fluvas; Fluvas (TN); Fluvastatin & Primycin; Fluvastatin (INN); Fluvastatin [INN:BAN]; Fluvastatina; Fluvastatina [INN-Spanish]; Fluvastatine; Fluvastatine [INN-French]; Fluvastatinum; Fluvastatinum [INN-Latin]; Lescol; Lescol (TN); Lescol XL; Vastin (TN); XU 62320; XU-62320
Drug Type
Small molecular drug
Indication Hypercholesterolemia [ICD11:5C80.0] Approved [1]
Therapeutic Class
Anticholesteremic Agents
Structure
3D MOL 2D MOL
Formula
C24H26FNO4
Canonical SMILES
CC(C)N1C2=CC=CC=C2C(=C1C=CC(CC(CC(=O)O)O)O)C3=CC=C(C=C3)F
InChI
InChI=1S/C24H26FNO4/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)/b12-11+/t18-,19-/m1/s1
InChIKey
FJLGEFLZQAZZCD-MCBHFWOFSA-N
CAS Number
CAS 93957-54-1
Pharmaceutical Properties Molecular Weight 411.5 Topological Polar Surface Area 82.7
Heavy Atom Count 30 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
XLogP
3.5
PubChem CID
446155
PubChem SID
100024002 ,10299838 ,103043439 ,103293858 ,104170157 ,104635874 ,10584685 ,10852031 ,117368355 ,121362529 ,126667384 ,130408282 ,131378297 ,135650279 ,136352753 ,136910868 ,137201916 ,143038598 ,144075757 ,144213082 ,14981407 ,152164360 ,152245639 ,162221786 ,163620805 ,163686130 ,165235894 ,172080782 ,175269733 ,175611054 ,176253518 ,176484235 ,24775765 ,36888653 ,46505668 ,47291222 ,48413791 ,48416032 ,49835750 ,49857384 ,50758963 ,53787111 ,56312811 ,56313633 ,57404724 ,7979295 ,822161 ,85856290 ,91613309 ,92308982
ChEBI ID
ChEBI:5136
TTD Drug ID
D08GHB
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [3]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [4]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [4]
P-GP Transporter Info P-glycoprotein 1 Substrate [5]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OATP1B1 Transporter Info Km =1.4 microM Chinese hamster ovary (CHO) cells-OATP1B1 [4]
OATP1B1 Transporter Info Km =3.5 microM Chinese hamster ovary (CHO) cells-OATP1B1 [4]
OATP1B1 Transporter Info Km =31.1 microM Oocytes-OATP1B1 [6]
OATP1B3 Transporter Info Km =7 microM Madin-Darby canine kidney cells (MDCKII)-OATP1B3 [7]
OATP2B1 Transporter Info Km =0.75 microM Human embryonic kidney cells (HEK293)-OATP2B1 [4]
References
1 Fluvastatin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Evaluation of the usefulness of breast cancer resistance protein (BCRP) knockout mice and BCRP inhibitor-treated monkeys to estimate the clinical impact of BCRP modulation on the pharmacokinetics of BCRP substrates. Pharm Res. 2015 May;32(5):1634-47.
3 SLCO1B1 polymorphism and sex affect the pharmacokinetics of pravastatin but not fluvastatin. Clin Pharmacol Ther. 2006 Oct;80(4):356-66.
4 Substrate-dependent drug-drug interactions between gemfibrozil, fluvastatin and other organic anion-transporting peptide (OATP) substrates on OATP1B1, OATP2B1, and OATP1B3. Drug Metab Dispos. 2007 Aug;35(8):1308-14.
5 A novel screening strategy to identify ABCB1 substrates and inhibitors. Naunyn Schmiedebergs Arch Pharmacol. 2009 Jan;379(1):11-26.
6 The effect of SLCO1B1*15 on the disposition of pravastatin and pitavastatin is substrate dependent: the contribution of transporting activity changes by SLCO1B1*15. Pharmacogenet Genomics. 2008 May;18(5):424-33.
7 Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8.

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