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Compound Detail

CHEMBL956

SUPROFEN
💊 Approved Drug
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💊 Approved Drug
CC(C(=O)O)c1ccc(C(=O)c2cccs2)cc1

Basic Information

ChEMBL ID CHEMBL956
Name SUPROFEN
Phase Approved
Structure Type MOL
InChI Key MDKGKXOCJGEUJW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

NSC-303611 P-(2-thenoyl)hydratropic acid P-2-thenoylhydratropic acid Profenal R-25,061 R-25061 Racemic suprofen Srendam Sulproltin Suprofen Suprofene Suprofeno +3 more
3
Targets
4
Activities
2
Assay Types
11
PK Parameters
20
Publications
15
Known Names
1
Indications
1
Mechanisms

Molecular Properties

260.3
MW (Da)
3.17
ALogP
3
HBA
1
HBD
54.4
PSA (Ų)
0.86
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Withdrawn
Chirality Racemic

Routes of Administration

Topical

Flags

Withdrawn Natural Product
USAN Stem -profen
USAN Year 1974

Extended Properties

Molecular Formula C14H12O3S
MW 260.31
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.81

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase

Indications

Rheumatic Diseases

ATC Classification

M01AE07
suprofen
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Withdrawn
nephrotoxicity
Flank pain, decreased kidney function
Country: United States; United Kingdom; Spain   Year: 1987
Withdrawn
musculoskeletal toxicity
Flank pain, decreased kidney function
Country: United States; United Kingdom; Spain   Year: 1987
Withdrawn
nephrotoxicity
Flank pain, decreased kidney function
Country: United States; United Kingdom; Spain   Year: 1987
Withdrawn
musculoskeletal toxicity
Flank pain, decreased kidney function
Country: United States; United Kingdom; Spain   Year: 1987

Activity Summary

IC50 2 meas. best 6.25
Ki 2 meas. best 5.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
IC50 6.25 6.25 560.0 1
Prostaglandin G/H synthase 2
CHEMBL230
IC50 5.56 5.56 2750.0 1
Cytochrome P450 2C9
CHEMBL3397
Ki 5.43 4.89 3700.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 0.76 mL.min-1.kg-1 Homo sapiens
CL 0.7 mL.min-1.kg-1 Homo sapiens
CL 0.76 mL.min-1.kg-1 Homo sapiens
CL 0.76 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 9.77 uL.min-1.(10^6cells)-1 Homo sapiens
CL 16.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
Fu 0.006 - Homo sapiens
Fu 0.006 - Homo sapiens
MRT 0.88 hr Homo sapiens
T1/2 2.1 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
7913134 10.1021/jm00039a010 Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
16019946 10.1080/00498250400028197 ADMET 4
- 10.6019/CHEMBL3301361 ADMET 3
16248836 10.2174/138920005774330639 Cytochrome P450 2C9 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
19445515 10.1021/jm900403j Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
7913134 10.1021/jm00039a010 Rattus norvegicus 2

Data from ChEMBL 36 via Core Engine