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Compound Detail

CHEMBL898

DIFLUNISAL
💊 Approved Drug
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💊 Approved Drug
O=C(O)c1cc(-c2ccc(F)cc2F)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL898
Name DIFLUNISAL
Phase Approved
Structure Type MOL
InChI Key HUPFGZXOMWLGNK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Diflunisal Dolobid Dolobid 500 NSC-756728
10
Targets
36
Activities
4
Assay Types
10
PK Parameters
20
Publications
4
Known Names
6
Indications
1
Mechanisms

Molecular Properties

250.2
MW (Da)
3.04
ALogP
2
HBA
2
HBD
57.5
PSA (Ų)
0.86
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -sal
USAN Year 1975

Extended Properties

Molecular Formula C13H8F2O3
MW 250.20
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.57

Mechanism of Action

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

Indications

Arthritis, Rheumatoid Fever Osteoarthritis Pain Amyloid Neuropathies, Familial Diabetes Mellitus, Type 2

ATC Classification

N02BA11
diflunisal
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Drug Warnings

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

Activity Summary

IC50 15 meas. best 6.07
Kd 14 meas. best 7.12
Ki 6 meas. best 5.68
EC50 1 meas. best 5.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transthyretin
CHEMBL3194
 Kd 7.12 6.0443 75.0 7
Solute carrier family 22 member 6
CHEMBL1641347
 IC50 6.07 6.07 850.0 1
Unchecked
CHEMBL612545
 Kd 5.94 5.94 1160.0 1
Albumin
CHEMBL3253
 Kd 5.91 5.715 1230.3 2
Transthyretin
CHEMBL3194
 Ki 5.68 5.68 2100.0 1
2-amino-3-carboxymuconate-6-semialdehyde decarboxylase
CHEMBL4105941
 Ki 5.59 5.59 2560.0 1
Carbonic anhydrase 2
CHEMBL205
 IC50 5.57 5.57 2700.0 1
Carbonic anhydrase 1
CHEMBL261
 IC50 5.47 5.47 3380.0 1
Transthyretin
CHEMBL3194
 IC50 5.46 5.072 3500.0 5
Transthyretin
CHEMBL3194
 EC50 5.25 5.25 5600.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 5.07 5.07 8450.0 1
Carbonic anhydrase 2
CHEMBL205
 Ki 5.03 5.03 9370.0 1
2-amino-3-carboxymuconate-6-semialdehyde decarboxylase
CHEMBL4105941
 IC50 4.87 4.87 13500.0 1
Unchecked
CHEMBL612545
 IC50 4.75 4.75 18000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.53 4.41 29800.0 2
Dihydrofolate reductase
CHEMBL202
 Ki 4.47 4.47 34000.0 1
Macrophage cell line
CHEMBL613891
 IC50 4.28 4.28 53000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.18 mL.min-1.kg-1 Homo sapiens
CL 0.1 mL.min-1.kg-1 Homo sapiens
CL 6.31 uL.min-1.(10^6cells)-1 Homo sapiens
CL 10.23 uL.min-1.(10^6cells)-1 Rattus norvegicus
Cmax 200000.0 nM Homo sapiens
F 80.0 % Homo sapiens
F 100.0 % Homo sapiens
Fu 0.0016 - Homo sapiens
MRT 14.0 hr Homo sapiens
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transthyretin Kd = 75.0 nM 7.12 Binding affinity to wild type TTR (unknown origin) expressed in Escherichia coli... 32914975
Transthyretin Kd = 407.0 nM 6.39 Binding affinity to transthyretin (unknown origin) by ITC method 30133284
Transthyretin Kd = 580.0 nM 6.24 Binding affinity to TTR (unknown origin) by isothermal titration calorimetric an... 26214366
Solute carrier family 22 member 6 IC50 = 850.0 nM 6.07 TP_TRANSPORTER: inhibition of Adefovir uptake in OAT1-expressing CHO cells 10991954
Unchecked Kd = 1160.0 nM 5.94 Binding affinity to human recombinant TTR Y78F mutant after 5 mins by isothermal... 24147937
Albumin Kd = 1230.27 nM 5.91 Binding affinity to human serum albumin by PAMPA method 18348514
Transthyretin Kd = 1300.0 nM 5.89 Binding affinity to TTR V30M mutant (unknown origin) by isothermal titration cal... 34547896
Transthyretin Kd = 1400.0 nM 5.85 Binding affinity to N-terminal hexa-histidine tagged TTR V30M mutant (unknown or... 37910439
Transthyretin Ki = 2100.0 nM 5.68 Inhibition of recombinant N-terminal hexa-histidine tagged TTR V30M mutant (unkn... 37910439
2-amino-3-carboxymuconate-6-semialdehyde decarboxylase Ki = 2560.0 nM 5.59 Competitive inhibition of human ACMSD using ACMS substrate by spectrometry 33369426
Transthyretin Kd = 2700.0 nM 5.57 Stabilization of wild type human transthyretin expressed in Escherichia coli BL2... 32124607
Carbonic anhydrase 2 IC50 = 2700.0 nM 5.57 Inhibition of human carbonic anhydrase 2 esterase activity by spectrophotometry 18819808
Albumin Kd = 3000.0 nM 5.52 Binding affinity to human serum albumin 28771355
Carbonic anhydrase 1 IC50 = 3380.0 nM 5.47 Inhibition of human carbonic anhydrase 1 esterase activity by spectrophotometry 18819808
Transthyretin IC50 = 3500.0 nM 5.46 Stabilization of TTR V30M mutant (unknown origin) assessed as acid-mediated prot... 34547896
Transthyretin Kd = 5600.0 nM 5.25 Stabilization of TTR V30M mutant (unknown origin) assessed as inhibition of prot... 32914975
Transthyretin EC50 = 5600.0 nM 5.25 Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli ass... 25314129
Transthyretin IC50 = 6300.0 nM 5.2 Inhibition of transthyretin V30M mutant (unknown origin) expressed in Escherichi... 24422526
Transthyretin IC50 = 6600.0 nM 5.18 Inhibition of acid-mediated aggregation of TTR V30M mutant (unknown origin) expr... 34225167
Carbonic anhydrase 1 Ki = 8450.0 nM 5.07 Inhibition of human carbonic anhydrase 1 esterase activity by noncompetitive Lin... 18819808

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 326
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
30108991 10.1039/C8MD00139A Macrophage cell line 9
30133284 10.1021/acs.jmedchem.8b00817 Transthyretin 9
34547896 10.1021/acs.jmedchem.1c00823 Transthyretin 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37910439 10.1021/acs.jmedchem.3c01698 Transthyretin 7
30108991 10.1039/C8MD00139A Streptococcus pyogenes 6
35074589 10.1016/j.ejmech.2022.114102 Unchecked 6
30108991 10.1039/C8MD00139A Staphylococcus aureus 6
30108991 10.1039/C8MD00139A Escherichia coli 6
30108991 10.1039/C8MD00139A Pseudomonas aeruginosa 6
30688456 10.1021/acs.jmedchem.8b01700 Transthyretin 6
30108991 10.1039/C8MD00139A Enterococcus faecium 6
30108991 10.1039/C8MD00139A Klebsiella pneumoniae 6
309947 10.1021/jm00209a001 Rattus norvegicus 6
26695731 10.1016/j.ejmech.2015.10.041 NON-PROTEIN TARGET 5
14711308 10.1021/jm030347n Transthyretin 5

Data from ChEMBL 36 via Core Engine