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Compound Detail

CHEMBL1144

PRAVASTATIN
💊 Approved Drug
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💊 Approved Drug
CC[C@H](C)C(=O)O[C@H]1C[C@H](O)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(=O)O)[C@H]21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1144
Name PRAVASTATIN
Phase Approved
Structure Type MOL
InChI Key TUZYXOIXSAXUGO-PZAWKZKUSA-N
Therapeutic ✓ Yes

Known Names

C10AA03 Pravastatin Pravastatina Pravastatine Pravator
12
Targets
31
Activities
3
Assay Types
30
PK Parameters
20
Publications
5
Known Names
20
Indications

Molecular Properties

424.5
MW (Da)
2.44
ALogP
6
HBA
4
HBD
124.3
PSA (Ų)
0.40
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -stat-
USAN Year 1988

Extended Properties

Molecular Formula C23H36O7
MW 424.53
Aromatic Rings 0
Heavy Atoms 30
NP-Likeness 2.18

Indications

Cardiovascular Diseases Carcinoma, Hepatocellular Diabetes Mellitus Heart Failure Hypercholesterolemia Hyperlipidemia, Familial Combined Hyperlipidemias Hyperlipoproteinemia Type III Hypertension Ischemic Stroke Lipid Metabolism Disorders Multiple Sclerosis, Relapsing-Remitting Myocardial Infarction Myocardial Ischemia Polycystic Kidney, Autosomal Dominant Pre-Eclampsia Renal Insufficiency, Chronic Breast Neoplasms Carcinoma Cardiomyopathies

ATC Classification

C10AA03
pravastatin
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Activity Summary

IC50 22 meas. best 8.25
Ki 6 meas. best 5.47
EC50 3 meas. best 5.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3-hydroxy-3-methylglutaryl-coenzyme A reductase
CHEMBL402
 IC50 8.25 7.39 5.6 3
3-hydroxy-3-methylglutaryl-coenzyme A reductase
CHEMBL3247
 IC50 7.89 7.695 13.0 2
Hepatocyte
CHEMBL613362
 IC50 7.77 7.6933 17.0 3
Unchecked
CHEMBL612545
 IC50 6.37 6.37 430.0 1
L6
CHEMBL614793
 IC50 5.82 5.3533 1519.0 3
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
 Ki 5.47 5.47 3400.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
 IC50 5.44 5.44 3600.0 1
HepG2
CHEMBL395
 IC50 5.29 5.29 5100.0 1
Mycobacterium tuberculosis
CHEMBL360
 EC50 5.11 5.11 7800.0 3
Organic anion transporter 3
CHEMBL1641348
 IC50 4.86 4.86 13700.0 1
Organic anion transporter 3
CHEMBL2073666
 IC50 4.81 4.81 15600.0 1
Solute carrier family 22 member 6
CHEMBL1777665
 Ki 4.28 4.28 52000.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
 Ki 4.24 4.24 57000.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
 IC50 4.21 4.21 62000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 7.7 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 26.98 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 3.105 mL.min-1.kg-1 Homo sapiens
CL 78.57 mL.min-1.kg-1 Rattus norvegicus
CL 27.5 mL.min-1.kg-1 Rattus norvegicus
CL 6.21 mL.min-1.kg-1 Homo sapiens
CL - - Homo sapiens
CL 1.77 mL.min-1.kg-1 Rattus norvegicus
CL 27.4 mL.min-1.kg-1 Rattus norvegicus
CL 6.723 mL.min-1.kg-1 Rattus norvegicus
CL 6.455 mL.min-1.kg-1 Rattus norvegicus
CL 0.77 mL.min-1.kg-1 Homo sapiens
CL 19.3 mL.min-1.kg-1 Rattus norvegicus
CL 34.6 mL.min-1.kg-1 Macaca fascicularis
CL 7.3 mL.min-1.kg-1 Homo sapiens
Cmax 100.0 nM Homo sapiens
F 17.0 % Homo sapiens
Fu 0.5 - Homo sapiens
Fu 0.5 - Homo sapiens
Fu 0.705 - Rattus norvegicus
Fu 0.00537 - Rattus norvegicus
Fu 0.00649 - Macaca fascicularis
Fu 0.00634 - Homo sapiens
MRT 0.59 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 5.591 nM 8.25 DRUGMATRIX: HMG-CoA Reductase enzyme inhibition (substrate: [14C]HMG-CoA) -
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 13.0 nM 7.89 Inhibition of HMG-CoA reductase in Sprague-Dawley rat liver microsomes 18072721
Hepatocyte IC50 = 17.0 nM 7.77 Inhibition of cholesterol synthesis in rat hepatocytes 18072721
Hepatocyte IC50 = 17.0 nM 7.77 Inhibition of cholesterol synthesis in rat hepatocyte 18155906
Hepatocyte IC50 = 29.0 nM 7.54 Inhibition of cholesterol synthesis in rat hepatocytes assessed as incorporation... 18412317
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 30.0 nM 7.52 Tested in vitro for the inhibition of HMG-CoA reductase from partially purified ... 1597859
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 31.6 nM 7.5 Inhibition of HMGR in rat hepatic microsomes assessed as conversion of [14C]HMG-... 18412317
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 400.0 nM 6.4 Inhibition of human HMGR catalytic domain using 800 uM HMG-CoA as substrate meas... 27228159
Unchecked IC50 = 430.0 nM 6.37 In vitro ability to inhibit cholesterol biosynthesis in HepG2 cells in culture f... 7650673
L6 IC50 = 1519.0 nM 5.82 Inhibition of cholesterol synthesis in rat L6 cells assessed as incorporation of... 18412317
Solute carrier organic anion transporter family member 1B1 Ki = 3400.0 nM 5.47 Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as r... 22541068
Solute carrier organic anion transporter family member 1B1 IC50 = 3600.0 nM 5.44 Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as r... 22541068
HepG2 IC50 = 5100.0 nM 5.29 In vitro inhibitory activity was evaluated on cholesterol biosynthesis in HepG2 ... 14741258
L6 IC50 = 7550.0 nM 5.12 Inhibition of cholesterol synthesis in rat L6 myocyte 18155906
L6 IC50 = 7600.0 nM 5.12 Inhibition of cholesterol synthesis in rat L6 cells 18072721
Mycobacterium tuberculosis EC50 = 7800.0 nM 5.11 Antitubercular activity against Mycobacterium tuberculosis H37Rv expressed in TH... 32126450
Mycobacterium tuberculosis EC50 = 7800.0 nM 5.11 Antitubercular activity against Mycobacterium tuberculosis H37Rv expressed in TH... 32126450
Mycobacterium tuberculosis EC50 = 7800.0 nM 5.11 Antitubercular activity against Mycobacterium tuberculosis H37Rv expressed in TH... 32126450
Organic anion transporter 3 IC50 = 13700.0 nM 4.86 TP_TRANSPORTER: inhibition of ES uptake (ES: 50nM) in hOAT3-expressing S2 cells 14978359
Organic anion transporter 3 IC50 = 15600.0 nM 4.81 TP_TRANSPORTER: inhibition of ES uptake (ES: 50nM) in rOAT3-expressing S2 cells 14978359

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 920
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
32985885 10.1021/acs.jmedchem.0c01033 ADMET 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
18412317 10.1021/jm800001n Cavia porcellus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
- 10.1039/C6MD00235H Solute carrier organic anion transporter family member 2B1 8
- 10.6019/CHEMBL3301361 ADMET 5
18779350 10.1128/aac.00513-08 Plasmodium falciparum 4
22190695 10.1124/dmd.111.042101 Hepatocyte 4
18426954 10.1124/dmd.108.020479 ADMET 4
22196621 10.1021/jm2014887 Hepatocyte 4
21467212 10.1124/dmd.111.039180 Liver microsome 3
27228159 10.1021/acs.jnatprod.5b00961 3-hydroxy-3-methylglutaryl-coenzyme A reductase 3
22541068 10.1021/jm300212s Solute carrier organic anion transporter family member 2B1 3
20014752 10.1021/tx900326k Hepatotoxicity 3
14610227 10.1124/jpet.103.060194 Solute carrier organic anion transporter family member 2B1 3
22541068 10.1021/jm300212s Solute carrier organic anion transporter family member 1B1 3

Data from ChEMBL 36 via Core Engine