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Compound Detail

CHEMBL56367

NIMESULIDE
💊 Approved Drug
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💊 Approved Drug
CS(=O)(=O)Nc1ccc([N+](=O)[O-])cc1Oc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL56367
Name NIMESULIDE
Phase Approved
Structure Type MOL
InChI Key HYWYRSMBCFDLJT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Aulin Nimesulida Nimesulide NSC-758412 R 805 R-805
14
Targets
44
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
5
Indications

Molecular Properties

308.3
MW (Da)
2.76
ALogP
5
HBA
1
HBD
98.5
PSA (Ų)
0.68
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C13H12N2O5S
MW 308.31
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -1.54

Indications

Arthralgia Myalgia Rheumatic Diseases Breast Neoplasms Pain

ATC Classification

M01AX17
nimesulide
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M02AA26
nimesulide
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN

Drug Warnings

Withdrawn
General Warning
Adverse health effects
Country: Nigeria; Bhutan; Ireland   Year: 2005
Withdrawn
hepatotoxicity
Hepatoxicity and neonatal renal failure
Country: Nigeria; Bhutan; Ireland   Year: 2005
Withdrawn
hepatotoxicity
Hepatoxicity and neonatal renal failure
Country: Nigeria; Bhutan; Ireland   Year: 2005
Withdrawn
hepatotoxicity
Liver damage
Country: Nigeria; Bhutan; Ireland   Year: 2005
Withdrawn
nephrotoxicity
Hepatoxicity and neonatal renal failure
Country: Nigeria; Bhutan; Ireland   Year: 2005
Withdrawn
hepatotoxicity
Liver damage
Country: Nigeria; Bhutan; Ireland   Year: 2005

Activity Summary

IC50 41 meas. best 7.82
Ki 3 meas. best 4.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 7.82 5.986 15.0 15
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 6.4 6.06 400.0 2
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 5.91 4.9991 1226.0 11
Myeloperoxidase
CHEMBL2439
 IC50 5.68 5.68 2100.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 5.21 5.21 6200.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 4.93 4.93 11826.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 4.83 4.83 14884.0 1
Unchecked
CHEMBL612545
 IC50 4.64 4.64 23000.0 1
Interstitial collagenase
CHEMBL332
 IC50 4.63 4.63 23345.0 1
Aromatase
CHEMBL1978
 IC50 4.57 4.57 27000.0 1
LNCaP
CHEMBL612518
 IC50 4.57 4.57 26690.0 1
HepG2
CHEMBL395
 IC50 4.45 4.45 35210.0 1
A549
CHEMBL392
 IC50 4.17 4.17 67810.0 1
Dipeptidyl peptidase 3
CHEMBL4105778
 Ki 4.16 4.16 70000.0 1
SK-BR-3
CHEMBL613834
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 15.0 nM 7.82 Inhibitory activity was evaluated against human Prostaglandin G/H synthase 2 was... 9871612
Prostaglandin G/H synthase 2 IC50 = 23.0 nM 7.64 Inhibition of purified COX2 assessed as formation of oxidized TMPD during reduct... 21542630
Prostaglandin G/H synthase 2 IC50 = 400.0 nM 6.4 Inhibition of ovine COX2 assessed as PGF2alpha level by EIA 21349729
Prostaglandin G/H synthase 2 IC50 = 600.0 nM 6.22 In vitro inhibition activity against cyclooxygenase 2 with the compound dissolve... 15993594
Prostaglandin G/H synthase 2 IC50 = 700.0 nM 6.16 Inhibition of COX2 in human whole blood assessed as inhibition of LPS-stimulated... 15615524
Prostaglandin G/H synthase 2 IC50 = 700.0 nM 6.16 Inhibition of COX2 in LPS-stimulated human whole blood assessed as PGE2 producti... 19791801
Prostaglandin G/H synthase 2 IC50 = 700.0 nM 6.16 Inhibition of COX2 21413808
Prostaglandin G/H synthase 2 IC50 = 700.0 nM 6.16 Inhibition of COX-2 in human whole blood assessed as PGE2 level in plasma after ... 24440378
Prostaglandin G/H synthase 1 IC50 = 1226.0 nM 5.91 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 1300.0 nM 5.89 The inhibitory activity against cyclooxygenase Prostaglandin G/H synthase 2 (COX... 12408728
Prostaglandin G/H synthase 2 IC50 = 1436.0 nM 5.84 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 1680.0 nM 5.78 Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate incubat... 35685617
Prostaglandin G/H synthase 2 IC50 = 1684.0 nM 5.77 Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate measure... 33071054
Prostaglandin G/H synthase 2 IC50 = 1920.0 nM 5.72 Inhibition of ovine COX-2 using arachidonic acid after 5 mins by colorimetric me... 26455657
Myeloperoxidase IC50 = 2100.0 nM 5.68 Inhibition of recombinant human myeloperoxidase 22793255
Prostaglandin G/H synthase 2 IC50 = 3500.0 nM 5.46 Inhibition of COX2 in LPS-stimulated human whole blood assessed as TXB2 producti... 19135376
Prostaglandin G/H synthase 1 IC50 = 3760.0 nM 5.42 Inhibition of COX1 in human whole blood assessed as inhibition of calcium ionoph... 15615524
Prostaglandin G/H synthase 1 IC50 = 3760.0 nM 5.42 Inhibition of COX1 in human whole blood assessed as TXB2 production by enzyme im... 19791801
Prostaglandin G/H synthase 1 IC50 = 3760.0 nM 5.42 Inhibition of COX1 21413808
Prostaglandin G/H synthase 1 IC50 = 3760.0 nM 5.42 Inhibition of COX-1 in human whole blood assessed as thromboxane B2 level in ser... 24440378

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1549
- 10.6019/CHEMBL3885881 Rattus norvegicus 458
26455657 10.1016/j.bmc.2015.10.007 Caco-2 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
33071054 10.1016/j.ejmech.2020.112918 Prostaglandin G/H synthase 2 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17845827 10.1016/j.ejmech.2007.06.023 Rattus norvegicus 7
- 10.1007/s00044-011-9774-2 Rattus norvegicus 6
24440378 10.1016/j.ejmech.2013.12.033 Rattus norvegicus 6
19791801 10.1021/jm900702b Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 Bile acid receptor 4
20171763 10.1016/j.ejmech.2010.01.059 Rattus norvegicus 4
28666860 10.1016/j.bmc.2017.06.009 MCF7 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
20133024 10.1016/j.ejmech.2010.01.029 Rattus norvegicus 4
17275312 10.1016/j.bmc.2007.01.013 Mus musculus 4
19172146 10.1038/nchembio.147 Danio rerio 4
27040659 10.1016/j.bmcl.2016.03.092 RAW264.7 3
26455657 10.1016/j.bmc.2015.10.007 No relevant target 3
15615524 10.1021/jm049480l Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine