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Compound Detail

CHEMBL469

KETOROLAC
💊 Approved Drug
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💊 Approved Drug
O=C(c1ccccc1)c1ccc2n1CCC2C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL469
Name KETOROLAC
Phase Approved
Structure Type MOL
InChI Key OZWKMVRBQXNZKK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ketorolac Ketorolaco
9
Targets
14
Activities
2
Assay Types
30
PK Parameters
20
Publications
2
Known Names
20
Indications

Molecular Properties

255.3
MW (Da)
2.29
ALogP
3
HBA
1
HBD
59.3
PSA (Ų)
0.86
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1989
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Withdrawn Natural Product
USAN Stem -ac
USAN Year 1984

Extended Properties

Molecular Formula C15H13NO3
MW 255.27
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.45

Indications

Eye Diseases Rheumatic Diseases Abdominal Pain Back Pain Breast Neoplasms Breast Neoplasms Cataract Deglutition Disorders Headache Inflammation Kidney Calculi Migraine Disorders Osteoarthritis Pain Wounds and Injuries Conjunctivitis, Viral Heart Diseases Kidney Neoplasms Kidney Neoplasms Miosis

ATC Classification

M01AB15
ketorolac
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
S01BC05
ketorolac
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Withdrawn
nephrotoxicity
severe adverse reactions including renal failure, some of which were fatal.
Country: Germany; France   Year: 1993
Withdrawn
General Warning
high frequency and seriousness of adverse drug reactions
Country: Germany; France   Year: 1993

Activity Summary

IC50 11 meas. best 7.89
Ki 3 meas. best 4.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 7.89 6.9 13.0 2
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.85 6.2267 140.0 3
Prostaglandin-H2 D-isomerase
CHEMBL4334
 IC50 6.64 6.64 230.0 1
Rho GTPase Rac1/CDC42
CHEMBL4106177
 IC50 5.7 5.7 2000.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 5.21 5.21 6109.0 1
Fatty acid-binding protein, liver
CHEMBL5738
 Ki 4.94 4.94 11600.0 1
Unchecked
CHEMBL612545
 IC50 4.89 4.89 13000.0 1
B16-F10
CHEMBL612656
 IC50 4.52 4.52 30000.0 1
Serine/threonine-protein kinase PAK 1
CHEMBL4600
 IC50 4.44 4.44 36000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 855.0 ng.hr.mL-1 Rattus norvegicus
CL 94.23 ml/hr Rattus norvegicus
CL 0.35 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 0.35 mL.min-1.kg-1 Homo sapiens
CL 0.35 mL.min-1.kg-1 Homo sapiens
CL 0.35 mL.min-1.kg-1 Homo sapiens
CL 0.6 mL.min-1.kg-1 Macaca
CL 1.3 mL.min-1.kg-1 Canis lupus familiaris
CL 3.6 mL.min-1.kg-1 Rattus norvegicus
CL 3.1 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Rattus norvegicus
CL 1.2 mL.min-1.kg-1 Macaca fascicularis
CL 0.19 mL.min-1.kg-1 Homo sapiens
Cmax 1566.97 nM Rattus norvegicus
F 80.0 % Homo sapiens
Fu 0.0068 - Homo sapiens
Fu 0.0068 - Homo sapiens
Fu 0.000216 - Rattus norvegicus
Fu 0.000148 - Macaca fascicularis
Fu 0.000264 - Homo sapiens
MRT 3.1 hr Rattus norvegicus
MRT 5.2 hr Homo sapiens
T1/2 4.0 hr -
T1/2 4.0 hr -
T1/2 4.0 hr -
T1/2 4.0 hr Rattus norvegicus
T1/2 1.65 hr Rattus norvegicus
T1/2 1.99 hr Rattus norvegicus
T1/2 0.39 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 1 IC50 = 13.0 nM 7.89 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 140.0 nM 6.85 Inhibition of recombinant human COX2 using arachidonic acid as substrate measure... 27889630
Prostaglandin-H2 D-isomerase IC50 = 230.0 nM 6.64 Concentration required to inhibit 50% activity of prostaglandin synthetase was d... 1900533
Prostaglandin G/H synthase 2 IC50 = 424.0 nM 6.37 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 1 IC50 = 1230.0 nM 5.91 Inhibition of human COX1 26994693
Rho GTPase Rac1/CDC42 IC50 = 2000.0 nM 5.7 Inhibition of RAC1/CDC42 in human ovarian cancer cells 27889630
Prostaglandin G/H synthase 2 IC50 = 3500.0 nM 5.46 Inhibition of human COX2 26994693
Aldo-keto reductase family 1 member B1 IC50 = 6109.0 nM 5.21 DRUGMATRIX: Aldose Reductase enzyme inhibition (substrate: DL-Glyceraldehyde) -
Fatty acid-binding protein, liver Ki = 11600.0 nM 4.94 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710
Unchecked IC50 = 13000.0 nM 4.89 Inhibition of PAK1/COX2 in human A549 cells harboring Ki-RAS mutant assessed as ... 27889630
B16-F10 IC50 = 30000.0 nM 4.52 Cytotoxicity against PAK1-independent mouse B16F10 cells assessed as cell growth... 27889630
Serine/threonine-protein kinase PAK 1 IC50 = 36000.0 nM 4.44 Inhibition of PAK1 in human A549 cells using myelin basic protein as substrate p... 27889630

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 295
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 54
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
19459639 10.1021/jm900051r Rattus norvegicus 9
4020827 10.1021/jm00146a011 Rattus norvegicus 9
19459639 10.1021/jm900051r Mus musculus 8
20070106 10.1021/jm901371v Homo sapiens 8
15920768 10.1002/jps.20373 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19913956 10.1016/j.ejmech.2009.10.031 Rattus norvegicus 5
16019946 10.1080/00498250400028197 ADMET 4
25975638 10.1016/j.bmc.2015.04.057 Rattus norvegicus 4
17967497 10.1016/j.ejmech.2007.09.011 No relevant target 4
18426954 10.1124/dmd.108.020479 ADMET 4
22386241 10.1016/j.bmcl.2012.02.023 Mus musculus 3
19459639 10.1021/jm900051r No relevant target 3

Data from ChEMBL 36 via Core Engine