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Compound Detail

CHEMBL563

FLURBIPROFEN
💊 Approved Drug
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💊 Approved Drug
CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL563
Name FLURBIPROFEN
Phase Approved
Structure Type MOL
InChI Key SYTBZMRGLBWNTM-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ansaid BTS 18,322 BTS-18322 Cebutid Flubiprofen Flurbiprofen Flurbiprofene Flurbiprofeno Froben Froben sr NSC-757037 Strefen +3 more
15
Targets
37
Activities
2
Assay Types
24
PK Parameters
20
Publications
15
Known Names
16
Indications
1
Mechanisms

Molecular Properties

244.3
MW (Da)
3.68
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.89
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1986
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Topical

Flags

Black Box Warning
USAN Stem -profen
USAN Year 1976

Extended Properties

Molecular Formula C15H13FO2
MW 244.26
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.43

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase ✓ ✓

Indications

Arthralgia Eye Diseases Miosis Myalgia Rheumatic Diseases Pain Pharyngitis Low Back Pain Periodontitis Anemia Anemia, Sickle Cell Arthritis, Rheumatoid Diabetes Mellitus, Type 2 Fractures, Bone HIV Infections Mitochondrial Diseases

ATC Classification

M01AE09
flurbiprofen
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M02AA19
flurbiprofen
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
R02AX01
flurbiprofen
Level 1: RESPIRATORY SYSTEM
Level 2: THROAT PREPARATIONS
S01BC04
flurbiprofen
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

IC50 31 meas. best 8.0
Ki 6 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 8.0 7.1267 10.0 3
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 8.0 6.6833 10.0 6
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 7.96 7.25 11.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.0 7.0 100.0 2
Microglia
CHEMBL4296521
 IC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 IC50 6.82 6.82 150.0 1
Prostaglandin G/H synthase 1
CHEMBL4042
 IC50 6.77 6.77 170.0 1
Aldo-keto reductase family 1 member C3
CHEMBL4681
 IC50 6.34 6.075 460.0 2
Prostaglandin G/H synthase 2
CHEMBL4321
 IC50 6.3 6.3 500.0 1
Aldo-keto reductase family 1 member C2
CHEMBL5847
 IC50 6.26 5.375 550.0 2
Prostaglandin G/H synthase 1
CHEMBL2949
 Ki 6.0 6.0 1000.0 1
Fatty acid-binding protein, liver
CHEMBL5738
 Ki 5.93 5.93 1180.0 1
Solute carrier family 22 member 6
CHEMBL1641347
 IC50 5.82 5.82 1500.0 1
Aldo-keto reductase family 1 member C1
CHEMBL5905
 IC50 5.69 5.69 2050.0 1
Aldo-keto reductase family 1 member C4
CHEMBL4999
 IC50 5.53 5.53 2980.0 1
Fatty acid-binding protein, intestinal
CHEMBL4879
 Ki 4.58 4.58 26000.0 1
Unchecked
CHEMBL612545
 Ki 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 311000.0 ng.hr.mL-1 Rattus norvegicus
AUC 78000.0 ng.hr.mL-1 Rattus norvegicus
AUC 130400.0 ng.hr.mL-1 Rattus norvegicus
AUC 19480.0 ng.hr.mL-1 Rattus norvegicus
CL 0.3183 mL.min-1.kg-1 Rattus norvegicus
CL 23.5 mL.min-1.g-1 Homo sapiens
CL 92.0 mL.min-1.kg-1 Homo sapiens
CL 5.94 uL.min-1.(10^6cells)-1 Homo sapiens
CL 0.45 mL.min-1.kg-1 Homo sapiens
CL 0.2157 mL.min-1.kg-1 Rattus norvegicus
Cmax 201015.31 nM Rattus norvegicus
Cmax 37255.38 nM Rattus norvegicus
Cmax 121182.35 nM Rattus norvegicus
F 80.0 % Homo sapiens
F 78.3 % Rattus norvegicus
F 66.94 % Rattus norvegicus
Fu 0.005 - Not specified
Fu 0.982 - Homo sapiens
T1/2 4.9 hr Rattus norvegicus
T1/2 5.1 hr Rattus norvegicus
T1/2 0.57 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus
Tmax 0.3 hr Rattus norvegicus
Tmax 0.5 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 = 10.0 nM 8.0 Inhibition of COX1 17341061
Prostaglandin G/H synthase 2 IC50 = 10.0 nM 8.0 Inhibition of COX2 17341061
Prostaglandin G/H synthase 2 IC50 = 10.0 nM 8.0 In vitro inhibitory activity against Prostaglandin G/H synthase 2 (COX-2) in hum... 10091674
Prostaglandin G/H synthase 1 IC50 = 11.0 nM 7.96 In vitro inhibitory activity against Prostaglandin G/H synthase 1 in sheep 10091674
Prostaglandin G/H synthase 1 IC50 = 12.0 nM 7.92 Reversible competitive inhibition of prostaglandin G/H synthase 1 14741265
Prostaglandin G/H synthase 1 IC50 = 21.0 nM 7.68 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Antineuroinflammatory activity in LPS-stimulated rat microglia cells assessed as... 22153874
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Antineuroinflammatory activity in rat brain neonatal microglia 24279991
Microglia IC50 = 100.0 nM 7.0 Antiinflammatory activity against LPS-induced rat Primary neonatal microglia ass... 32282204
Prostaglandin G/H synthase 1 IC50 = 150.0 nM 6.82 Inhibition of ovine COX1 assessed as production of PGF2-alpha preincubated with ... 26774927
Unchecked IC50 = 150.0 nM 6.82 In Vitro COX Assay: COX activity was measured using a commercial kit (COX Inhibi... -
Prostaglandin G/H synthase 1 IC50 = 170.0 nM 6.77 Concentration required to inhibit cyclooxygenase-1 in rat blood 16134939
Prostaglandin G/H synthase 2 IC50 = 359.0 nM 6.45 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Aldo-keto reductase family 1 member C3 IC50 = 460.0 nM 6.34 Inhibition of human recombinant AKR1C3 transfected in Escherichia coli BL21 (DE3... 37409679
Prostaglandin G/H synthase 1 IC50 = 500.0 nM 6.3 Inhibition of ovine COX1 20188577
Prostaglandin G/H synthase 2 IC50 = 500.0 nM 6.3 Inhibition of mouse COX2 20188577
Aldo-keto reductase family 1 member C2 IC50 = 550.0 nM 6.26 Inhibition of human recombinant AKR1C2 transfected in Escherichia coli BL21 (DE3... 37409679
Prostaglandin G/H synthase 1 Ki = 1000.0 nM 6.0 Binding affinity of compound towards prostaglandin G/H synthase 1 was evaluated 14741265
Prostaglandin G/H synthase 2 IC50 = 1040.0 nM 5.98 In Vitro COX Assay: COX activity was measured using a commercial kit (COX Inhibi... -
Prostaglandin G/H synthase 2 IC50 = 1060.0 nM 5.97 Inhibition of recombinant human COX2 assessed as production of PGF2-alpha preinc... 26774927

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 337
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
16134939 10.1021/jm0502541 ADMET 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
38107175 10.1039/d3md00357d ADMET 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
32089390 10.1016/j.bmc.2020.115374 BV-2 7
36921526 10.1016/j.ejmech.2023.115253 BV-2 7
29409707 10.1016/j.bmc.2018.01.030 BV-2 7
21405086 10.1021/jm101450p N2a 6
26810835 10.1016/j.bmc.2016.01.013 NON-PROTEIN TARGET 6
30470598 10.1016/j.bmc.2018.11.015 Unchecked 6
21405086 10.1021/jm101450p RAW264.7 5
30772129 10.1016/j.bmc.2019.01.040 BV-2 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
6827541 10.1021/jm00356a020 Homo sapiens 4
38107175 10.1039/d3md00357d No relevant target 4
16019946 10.1080/00498250400028197 ADMET 4
18395299 10.1016/j.ejmech.2008.01.039 Rattus norvegicus 4

Data from ChEMBL 36 via Core Engine