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Compound Detail

CHEMBL1043

DAPSONE
💊 Approved Drug
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💊 Approved Drug
Nc1ccc(S(=O)(=O)c2ccc(N)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1043
Name DAPSONE
Phase Approved
Structure Type MOL
InChI Key MQJKPEGWNLWLTK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Aczone Dapsona Dapsone Dapsonum Diaminodiphenylsulfone Diaphenylsulfone J04BA02 Novophone NSC-6091 NSC-6091D Servidapson
8
Targets
19
Activities
2
Assay Types
17
PK Parameters
20
Publications
11
Known Names
18
Indications
1
Mechanisms

Molecular Properties

248.3
MW (Da)
1.68
ALogP
4
HBA
2
HBD
86.2
PSA (Ų)
0.79
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1979
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Topical

Flags

Natural Product
USAN Year 1963

Extended Properties

Molecular Formula C12H12N2O2S
MW 248.31
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -0.74

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dihydropteroate synthase 1 inhibitor INHIBITOR Dihydropteroate synthase ✓ ✓

Indications

Acne Vulgaris Dermatitis Herpetiformis Leprosy Fever HIV Infections Malaria Malaria, Falciparum Malaria, Vivax Pneumonia, Pneumocystis Severe Acute Respiratory Syndrome Carcinoma, Non-Small-Cell Lung Lung Diseases Pemphigoid, Benign Mucous Membrane Pemphigus Pulmonary Fibrosis Rosacea Sarcoidosis Stroke

ATC Classification

D10AX05
dapsone
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
J04BA02
dapsone
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOBACTERIALS

Activity Summary

IC50 17 meas. best 6.38
Ki 2 meas. best 6.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 6.74 6.74 183.0 1
Myeloperoxidase
CHEMBL2439
 IC50 6.38 6.38 420.0 1
Unchecked
CHEMBL612545
 IC50 5.93 5.515 1180.0 4
Dihydrofolate reductase
CHEMBL1926
 IC50 5.82 5.82 1500.0 1
Plasmodium vivax
CHEMBL613013
 IC50 5.79 5.79 1625.0 1
Dihydropteroate synthetase, putative
CHEMBL1741265
 IC50 4.91 4.91 12410.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.75 4.75 18000.0 1
Lacticaseibacillus casei
CHEMBL613075
 IC50 4.12 4.12 75000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.48 mL.min-1.kg-1 Homo sapiens
CL 0.4 mL.min-1.kg-1 Homo sapiens
CL 0.48 mL.min-1.kg-1 Homo sapiens
CL 0.48 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 2.1 mL.min-1.kg-1 Mus musculus
CL 2.3 uL.min-1.(10^6cells)-1 Homo sapiens
CL 0.48 mL.min-1.kg-1 Homo sapiens
F 93.0 % Homo sapiens
Fu 0.25 - Homo sapiens
Fu 0.25 - Homo sapiens
Fu 0.25 - Homo sapiens
MRT 29.0 hr Homo sapiens
T1/2 22.0 hr Homo sapiens
T1/2 4.5 hr Mus musculus
T1/2 22.0 hr Homo sapiens
T1/2 216.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 6 Ki = 183.0 nM 6.74 Antagonist activity at recombinant human 5-HT6 receptor expressed in HEK293 cell... 23787290
Myeloperoxidase IC50 = 420.0 nM 6.38 Inhibition of MPO (unknown origin) 30466896
Unchecked IC50 = 1180.0 nM 5.93 Inhibitory activity against dihydropteroic acid synthase (SYN) from Mycobacteriu... 14695838
Unchecked IC50 = 1200.0 nM 5.92 Inhibitory activity against dihydropteroic acid synthase (SYN) from Mycobacteriu... 14695838
Dihydrofolate reductase IC50 = 1500.0 nM 5.82 Inhibitory activity was determined against dihydrofolate reductase in Pneumocyst... 7490723
Plasmodium vivax IC50 = 1625.0 nM 5.79 Antimalarial activity against Plasmodium vivax infected in human blood incubated... 31911292
Unchecked IC50 = 1780.0 nM 5.75 Inhibitory activity against dihydropteroic acid synthase (SYN) from candida albi... 14695838
Dihydropteroate synthetase, putative IC50 = 12410.0 nM 4.91 Inhibitory activity against dihydropteroic acid synthase (SYN) from Plasmodium b... 14695838
Plasmodium falciparum IC50 = 18000.0 nM 4.75 Antimicrobial activity against Plasmodium falciparum 20185316
Unchecked IC50 = 34360.0 nM 4.46 Inhibitory activity against dihydropteroic acid synthase (SYN) from Escherichia ... 14695838
Lacticaseibacillus casei IC50 = 75000.0 nM 4.12 Antibacterial activity against chlorguanide triazine-resistant Lactobacillus cas... 137981

Literature References

PubMed DOI Target Context # Activities
31103404 10.1016/j.bmc.2019.04.032 Mycobacterium leprae 20
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
17371812 10.1128/aac.01607-06 Plasmodium falciparum 10
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
9871632 10.1016/s0960-894x(97)10192-5 Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
14695838 10.1021/jm030931w Unchecked 4
137981 10.1021/jm00212a010 Lacticaseibacillus casei 4
9873564 10.1016/s0960-894x(98)00404-1 Mus musculus 3
137981 10.1021/jm00212a010 NON-PROTEIN TARGET 3
31103404 10.1016/j.bmc.2019.04.032 ADMET 3
20014752 10.1021/tx900326k Hepatotoxicity 3
3546688 10.1021/jm00386a004 Dihydropteroate synthase 2
17311370 10.1021/jm060706p Cytochrome P450 2C9 2
137981 10.1021/jm00212a010 Enterococcus faecium 2
2677378 10.1021/jm00130a028 Unchecked 2
19445515 10.1021/jm900403j Homo sapiens 2
137981 10.1021/jm00212a010 Escherichia coli 2

Data from ChEMBL 36 via Core Engine