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Compound Detail

CHEMBL704

MESALAMINE
💊 Approved Drug
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💊 Approved Drug
Nc1ccc(O)c(C(=O)O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL704
Name MESALAMINE
Phase Approved
Structure Type MOL
InChI Key KBOPZPXVLCULAV-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Apriso Asacol Asacol hd Benzoic acid, 5-amino-2-hydroxy- Canasa Coltec ec Delzicol Fisalamine Iialda Ipocol Lialda MAX-002 +12 more
8
Targets
15
Activities
1
Assay Types
5
PK Parameters
20
Publications
24
Known Names
19
Indications
3
Mechanisms

Molecular Properties

153.1
MW (Da)
0.67
ALogP
3
HBA
3
HBD
83.5
PSA (Ų)
0.41
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Topical

Flags

Natural Product
USAN Stem -sal-
USAN Year 1986

Extended Properties

Molecular Formula C7H7NO3
MW 153.14
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness 0.23

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Arachidonate 5-lipoxygenase inhibitor INHIBITOR Polyunsaturated fatty acid 5-lipoxygenase ✓ ✓
Peroxisome proliferator-activated receptor gamma agonist AGONIST Peroxisome proliferator-activated receptor gamma ✓ ✓
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase ✓ ✓

Indications

Colitis, Ulcerative Proctitis Colitis, Collagenous Colitis, Lymphocytic Crohn Disease Diverticular Diseases Diverticulitis Irritable Bowel Syndrome Adenoma Colitis Colorectal Neoplasms Colorectal Neoplasms, Hereditary Nonpolyposis Digestive System Diseases Diverticulum, Colon Eosinophilic Esophagitis Inflammatory Bowel Diseases Berylliosis HIV Infections Malnutrition

ATC Classification

A07EC02
mesalazine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS

Activity Summary

IC50 15 meas. best 6.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thiosulfate sulfurtransferase
CHEMBL4295835
 IC50 6.55 6.55 280.0 1
GroEL/GroES
CHEMBL4106139
 IC50 6.31 5.765 490.0 2
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 5.12 5.12 7530.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 5.11 5.11 7730.0 1
2-Hydroxyacid oxidase 1
CHEMBL4295985
 IC50 5.11 5.11 7800.0 1
Unchecked
CHEMBL612545
 IC50 5.08 5.08 8290.0 1
HSP60/HSP10
CHEMBL4106131
 IC50 4.92 4.92 12000.0 1
Tumor necrosis factor
CHEMBL1825
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 9.3 mL.min-1.kg-1 Homo sapiens
F 28.0 % Homo sapiens
Fu 0.39 - Homo sapiens
MRT 0.59 hr Homo sapiens
T1/2 0.61 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thiosulfate sulfurtransferase IC50 = 280.0 nM 6.55 Inhibition of native rhodanese (unknown origin) assessed as reduction in rhodane... 30852084
GroEL/GroES IC50 = 490.0 nM 6.31 Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Esch... 30852084
GroEL/GroES IC50 = 6000.0 nM 5.22 Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Esche... 30852084
Prostaglandin G/H synthase 2 IC50 = 7530.0 nM 5.12 Inhibition of recombinant human COX2 using arachidonic acid as substrate pretrea... 31301566
2-Hydroxyacid oxidase 1 IC50 = 7800.0 nM 5.11 Inhibition of mouse recombinant glycolate oxidase expressed in Escherichia coli ... 30028141
Prostaglandin G/H synthase 1 IC50 = 7730.0 nM 5.11 Inhibition of ovine COX1 using arachidonic acid as substrate pretreated for 5 mi... 31301566
Unchecked IC50 = 8290.0 nM 5.08 PUBCHEM_BIOASSAY: A biochemical assay using the ADP-Hunter methodology, purified... -
HSP60/HSP10 IC50 = 12000.0 nM 4.92 Inhibition of human N-terminal octa-His-tagged HSP60 expressed in Escherichia co... 30852084
Tumor necrosis factor IC50 = 20000.0 nM 4.7 Inhibition of TNFalpha (unknown origin)-induced adhesion of BCECF fluorescence-l... 30151084

Literature References

PubMed DOI Target Context # Activities
35442672 10.1021/acs.jmedchem.1c02198 Mus musculus 26
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
33839254 10.1016/j.bmcl.2021.128029 Rattus norvegicus 11
36053746 10.1021/acs.jmedchem.2c00390 Mus musculus 10
33556569 10.1016/j.bmcl.2021.127844 Mus musculus 8
27255176 10.1016/j.bmc.2016.05.047 Mus musculus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
21430235 10.1124/dmd.110.034991 Solute carrier organic anion transporter family member 1B1 8
21430235 10.1124/dmd.110.034991 ADMET 8
38913701 10.1021/acs.jmedchem.4c00202 Mus musculus 7
21430235 10.1124/dmd.110.034991 Solute carrier organic anion transporter family member 1B3 7
21430235 10.1124/dmd.110.034991 Solute carrier organic anion transporter family member 2B1 7
25937011 10.1016/j.bmcl.2015.04.023 Rattus norvegicus 6
32223194 10.1021/acs.jmedchem.9b01663 Mus musculus 5
6136612 10.1021/jm00363a015 Cavia porcellus 5
28646757 10.1016/j.ejmech.2017.06.018 HT-29 5
38687956 10.1021/acs.jmedchem.4c00222 Mus musculus 5
18070971 10.1128/aac.00678-07 Mycobacterium avium subsp. paratuberculosis 5

Data from ChEMBL 36 via Core Engine