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Compound Detail

CHEMBL1539

SULFADOXINE
💊 Approved Drug
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💊 Approved Drug
COc1ncnc(NS(=O)(=O)c2ccc(N)cc2)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1539
Name SULFADOXINE
Phase Approved
Structure Type MOL
InChI Key PJSFRIWCGOHTNF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Fanasulf J21.373J NSC-759319 RO 4-4393 RO-4-4393 RO-44393 Sulfadoxin Sulfadoxina Sulfadoxine Sulfadoxine component of fansidar Sulfadoxinum Sulforthamidine +3 more
2
Targets
6
Activities
2
Assay Types
0
PK Parameters
20
Publications
15
Known Names
8
Indications
1
Mechanisms

Molecular Properties

310.3
MW (Da)
0.88
ALogP
7
HBA
2
HBD
116.4
PSA (Ų)
0.79
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem sulfa-
USAN Year 1968

Extended Properties

Molecular Formula C12H14N4O4S
MW 310.34
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -1.08

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dihydropteroate synthetase inhibitor INHIBITOR Dihydropteroate synthetase ✓ ✓

Indications

Anemia HIV Infections Malaria Malaria, Falciparum Malaria, Vivax Pneumonia, Pneumocystis Pregnancy Premature Birth

Activity Summary

IC50 4 meas. best 7.4
EC50 2 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 EC50 7.52 7.52 30.0 1
Plasmodium falciparum
CHEMBL364
 IC50 7.4 5.465 40.0 4
SARS-CoV-2
CHEMBL4303835
 EC50 4.45 4.45 35370.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 30.0 nM 7.52 Antimalarial activity Plasmodium falciparum 3D7 20610151
Plasmodium falciparum IC50 = 40.0 nM 7.4 Antimalarial activity against chloroquine-resistant Plasmodium falciparum D6 by ... 19191586
Plasmodium falciparum IC50 = 6100.0 nM 5.21 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum W2 by ... 19191586
Plasmodium falciparum IC50 = 15000.0 nM 4.82 Antimalarial activity against chloroquine/sulfadoxine-resistant Plasmodium falci... 27485600
SARS-CoV-2 EC50 = 35370.0 nM 4.45 Antiviral efficacy against SARS-CoV-2 (strain BavPat1) in Vero E6 cells assessed... -
Plasmodium falciparum IC50 = 37000.0 nM 4.43 Antimicrobial activity against Plasmodium falciparum 20185316

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 430
17371812 10.1128/aac.01607-06 Plasmodium falciparum 10
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.1101/2020.04.03.023846 SARS-CoV-2 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
26190461 10.1016/j.bmc.2015.06.056 Plasmodium berghei 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
22931300 10.1021/tx300075j Liver microsomes 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
22633120 10.1016/j.bmc.2012.04.060 Mycobacterium tuberculosis 2
17574307 10.1016/j.ejmech.2007.04.009 No relevant target 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
19191586 10.1021/jm8008103 ADMET 2
19191586 10.1021/jm8008103 Plasmodium falciparum 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
22931300 10.1021/tx300075j Cytochrome P450 2C19 1

Data from ChEMBL 36 via Core Engine