Drug Information

General Information
Drug ID
DR00045
Drug Name
Pravastatin
Synonyms
(3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid; (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid; 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, (1S-(1alpha(betaS*,deltaS*),2alpha,6alpha,8beta(R*),8aalpha))-1-Naphthaleneheptanoic acid; Eptastatin; KS-5015; Oliprevin; Pravachol (TN); Pravastatin (INN); Pravastatin Sodium Salt; Pravastatin [INN:BAN]; Pravastatin tert-Octylamine Salt; Pravastatina; Pravastatina [Spanish]; Pravastatine; Pravastatine [French]; Pravastatinum; Pravastatinum [Latin]; Pravator; Pravator (TN); RMS-431; SQ-31,000; Selektine (TN); Vasten
Drug Type
Small molecular drug
Indication Hypercholesterolemia [ICD11:5C80.0] Approved [1]
Therapeutic Class
Anticholesteremic Agents
Structure
3D MOL 2D MOL
Formula
C23H36O7
Canonical SMILES
CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)O)O)O)O
InChI
InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
InChIKey
TUZYXOIXSAXUGO-PZAWKZKUSA-N
CAS Number
CAS 81093-37-0
Pharmaceutical Properties Molecular Weight 424.5 Topological Polar Surface Area 124
Heavy Atom Count 30 Rotatable Bond Count 11
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
XLogP
1.6
PubChem CID
54687
PubChem SID
102979949 ,104234199 ,104305598 ,10852022 ,117544687 ,118048679 ,124899367 ,126665388 ,129317935 ,134337841 ,135014686 ,135610132 ,135650848 ,137002685 ,142742106 ,14758460 ,14880512 ,152034648 ,152164597 ,160963523 ,164814679 ,165235255 ,174007284 ,175266850 ,175426985 ,175612187 ,179148899 ,184545482 ,187072512 ,210279284 ,210281607 ,223554816 ,223682192 ,223745588 ,226393956 ,34718661 ,46504851 ,48416457 ,4962 ,49688762 ,49995722 ,50718915 ,57288813 ,57313644 ,7980374 ,8183732 ,85789083 ,85856288 ,93166931 ,96025096
ChEBI ID
CHEBI:63618
TTD Drug ID
D02RQU
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
BSEP Transporter Info Bile salt export pump Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
OAT3 Transporter Info Organic anion transporter 3 Substrate [5]
OAT4 Transporter Info Organic anion transporter 4 Substrate [6]
OAT7 Transporter Info Organic anion transporter 7 Substrate [7]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [8]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [9]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [10]
P-GP Transporter Info P-glycoprotein 1 Substrate [11]
SLC17A4 Transporter Info Probable small intestine urate exporter Substrate [12]
Drug-Transporter Activity Data
Drug-Transporter Activity Data BSEP Transporter Info Km =124 microM Human embryonic kidney cells (HEK293)-BSEP [3]
OAT3 Transporter Info Km =27.2 microM Proximal tubule (S2) cells-OAT3 [6]
OAT4 Transporter Info Km =257 microM Proximal tubule (S2) cells-OAT4 [6]
OAT7 Transporter Info Km =1 microM Vector-transfected cells-OAT7 [7]
OATP1B1 Transporter Info Km =33.7 microM Human embryonic kidney cells (HEK293)-OATP1B1 [13]
OATP1B1 Transporter Info Km =85.7 microM Human embryonic kidney cells (HEK293)-OATP1B1 [14]
OATP1B1 Transporter Info Km =57.5 microM Oocytes-OATP1B1 [8]
OATP2B1 Transporter Info Km =2250 microM Human embryonic kidney cells (HEK293)-OATP2B1 [10]
References
1 Pravastatin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
3 Bile salt export pump (BSEP/ABCB11) can transport a nonbile acid substrate, pravastatin. J Pharmacol Exp Ther. 2005 Aug;314(2):876-82.
4 Role of transporters in the tissue-selective distribution and elimination of drugs: transporters in the liver, small intestine, brain and kidney. J Control Release. 2002 Jan 17;78(1-3):43-54.
5 Prediction of the overall renal tubular secretion and hepatic clearance of anionic drugs and a renal drug-drug interaction involving organic anion transporter 3 in humans by in vitro uptake experiments. Drug Metab Dispos. 2011 Jun;39(6):1031-8.
6 Inhibition of human organic anion transporter 3 mediated pravastatin transport by gemfibrozil and the metabolites in humans. Xenobiotica. 2007 Apr;37(4):416-26.
7 Variability in hepatic expression of organic anion transporter 7/SLC22A9, a novel pravastatin uptake transporter: impact of genetic and regulatory factors. Pharmacogenomics J. 2016 Aug;16(4):341-51.
8 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.
9 Relevance of conserved lysine and arginine residues in transmembrane helices for the transport activity of organic anion transporting polypeptide 1B3. Br J Pharmacol. 2010 Feb 1;159(3):698-708.
10 Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human. J Pharmacol Exp Ther. 2004 Feb;308(2):438-45.
11 Tarascon Pocket Pharmacopoeia 2018 Classic Shirt-Pocket Edition.
12 A Na+-phosphate cotransporter homologue (SLC17A4 protein) is an intestinal organic anion exporter. Am J Physiol Cell Physiol. 2012 Jun 1;302(11):C1652-60.
13 A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J Biol Chem. 1999 Dec 24;274(52):37161-8.
14 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.

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