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Compound Detail

CHEMBL1020

TOLMETIN
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(C(=O)c2ccc(CC(=O)O)n2C)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1020
Name TOLMETIN
Phase Approved
Structure Type MOL
InChI Key UPSPUYADGBWSHF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

MCN-2559 Tolmetin Tolmetina Tolmetine
6
Targets
10
Activities
2
Assay Types
6
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

257.3
MW (Da)
2.19
ALogP
3
HBA
1
HBD
59.3
PSA (Ų)
0.85
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1976
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1971

Extended Properties

Molecular Formula C15H15NO3
MW 257.29
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.60

Indications

Arthralgia Myalgia Rheumatic Diseases

ATC Classification

M01AB03
tolmetin
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M02AA21
tolmetin
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN

Activity Summary

IC50 6 meas. best 7.39
Ki 4 meas. best 4.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 7.39 6.925 41.0 2
Interleukin-8
CHEMBL2157
 IC50 7.05 7.05 90.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.09 6.09 820.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 5.67 5.67 2153.0 1
Aldo-keto reductase family 1 member B1
CHEMBL1900
 IC50 5.62 5.62 2390.0 1
Lactoylglutathione lyase
CHEMBL2424
 Ki 4.06 4.06 87800.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 4.0 mL.min-1.g-1 Homo sapiens
CL 7.33 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 9.12 uL.min-1.(10^6cells)-1 Homo sapiens
F 80.0 % Homo sapiens
T1/2 19.0 hr Homo sapiens
T1/2 0.2233 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 1 IC50 = 41.0 nM 7.39 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Interleukin-8 IC50 = 90.0 nM 7.05 Inhibition of CXCL8-induced chemotaxis in human polymorphonuclear leukocyte pret... 19560921
Prostaglandin G/H synthase 1 IC50 = 350.0 nM 6.46 Inhibition of COX-1 in human whole blood preincubated for 60 mins followed by ca... 37148849
Prostaglandin G/H synthase 2 IC50 = 820.0 nM 6.09 Inhibition of COX-2 in human whole blood incubated for 18 hrs by radioimmunoassa... 37148849
Aldo-keto reductase family 1 member B1 IC50 = 2153.0 nM 5.67 DRUGMATRIX: Aldose Reductase enzyme inhibition (substrate: DL-Glyceraldehyde) -
Aldo-keto reductase family 1 member B1 IC50 = 2390.0 nM 5.62 Inhibition of Homo sapiens (human) aldose reductase -
Lactoylglutathione lyase Ki = 87800.0 nM 4.06 Inhibition of glyoxalase 1 21237663
Lactoylglutathione lyase Ki = 87800.0 nM 4.06 Inhibition of human glyoxalase 1 21689932

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
6972450 10.1021/jm00137a022 Mus musculus 6
- 10.6019/CHEMBL3301361 ADMET 6
6827541 10.1021/jm00356a020 Homo sapiens 4
21601448 10.1016/j.bmcl.2011.04.133 No relevant target 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
24249037 10.1007/s11095-013-1232-z No relevant target 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
21237663 10.1016/j.bmc.2010.12.039 Lactoylglutathione lyase 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
33369426 10.1021/acs.jmedchem.0c01762 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase 2
15801837 10.1021/jm049227l Albumin 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2
3820215 10.1021/jm00386a001 Homo sapiens 2

Data from ChEMBL 36 via Core Engine