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Compound Detail

CHEMBL437

SULFATHIAZOLE
💊 Approved Drug
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💊 Approved Drug
Nc1ccc(S(=O)(=O)Nc2nccs2)cc1

Basic Information

ChEMBL ID CHEMBL437
Name SULFATHIAZOLE
Phase Approved
Structure Type MOL
InChI Key JNMRHUJNCSQMMB-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

NSC-31812 NSC-683531 Sulfathiazol Sulfathiazole Sulfathiazole (triple sulfa) Sulfathiazole (triple sulfa) component of sultrin Sulfathiazole component of gyne-sulf Sulfathiazole component of sultrin Sulfathiazole component of trysul Sulfathiazole component of vagilia Sulfatiazol Thiazamide +1 more
8
Targets
15
Activities
2
Assay Types
0
PK Parameters
20
Publications
13
Known Names
1
Indications
1
Mechanisms

Molecular Properties

255.3
MW (Da)
1.53
ALogP
5
HBA
2
HBD
85.1
PSA (Ų)
0.81
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1945
Availability Withdrawn
Chirality Achiral

Routes of Administration

Topical

Flags

Withdrawn Natural Product
USAN Stem sulfa-

Extended Properties

Molecular Formula C9H9N3O2S2
MW 255.32
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -2.09

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial dihydropteroate synthase inhibitor INHIBITOR Dihydropteroate synthase

Indications

Bacterial Infections

ATC Classification

D06BA02
sulfathiazole
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
J01EB07
sulfathiazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Drug Warnings

Withdrawn
nephrotoxicity
renal complications, rash, fever, blood dyscrasias, and liver damage
Country: United States; Philippines; Dominican Republic   Year: 1970
Withdrawn
hepatotoxicity
renal complications, rash, fever, blood dyscrasias, and liver damage
Country: United States; Philippines; Dominican Republic   Year: 1970
Withdrawn
dermatological toxicity
renal complications, rash, fever, blood dyscrasias, and liver damage
Country: United States; Philippines; Dominican Republic   Year: 1970
Withdrawn
General Warning
crystalluria
Country: United States; Philippines; Dominican Republic   Year: 1970
Withdrawn
General Warning
serious side effects
Country: United States; Philippines; Dominican Republic   Year: 1970
Withdrawn
hematological toxicity
renal complications, rash, fever, blood dyscrasias, and liver damage
Country: United States; Philippines; Dominican Republic   Year: 1970
Withdrawn
hepatotoxicity
renal complications, rash, fever, blood dyscrasias, and liver damage
Country: United States; Philippines; Dominican Republic   Year: 1970

Activity Summary

IC50 13 meas. best 5.6
Ki 2 meas. best 4.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydropteroate synthase
CHEMBL4032
IC50 5.6 5.6 2500.0 1
Unchecked
CHEMBL612545
IC50 5.12 4.7433 7550.0 3
Escherichia coli
CHEMBL354
IC50 5.11 5.11 7800.0 1
Transcriptional activator protein LasR
CHEMBL1075207
IC50 5.05 5.05 9000.0 2
Unchecked
CHEMBL612545
Ki 4.85 4.85 14000.0 1
No relevant target
CHEMBL2362975
IC50 4.28 4.28 52095.0 1
Endothelin-1 receptor
CHEMBL252
IC50 4.16 4.16 69000.0 1
Endothelin-1 receptor
CHEMBL4566
IC50 4.16 4.16 69000.0 1
Protein arginine N-methyltransferase 6
CHEMBL1275221
IC50 3.37 3.37 430000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydropteroate synthase IC50 = 2500.0 nM 5.6 In vitro inhibition of dihydropteroate synthase from Escherichia coli. 3906132
Unchecked IC50 = 7550.0 nM 5.12 PUBCHEM_BIOASSAY: High Throughput Screening Assay used to Identify Novel Compoun... -
Escherichia coli IC50 = 7800.0 nM 5.11 Antibacterial activity against sensitive Escherichia coli ATCC 10536 assessed as... 137981
Transcriptional activator protein LasR IC50 = 9000.0 nM 5.05 Inhibition of LasR in Pseudomonas aeruginosa harboring GFP-fused quorum sensing ... 29999316
Transcriptional activator protein LasR IC50 = 9000.0 nM 5.05 Inhibition of LasR-mediated quorum sensing system in Pseudomonas aeruginosa PAO1... 38801798
Unchecked IC50 = 10260.0 nM 4.99 PUBCHEM_BIOASSAY: A High Throughput Confirmatory Assay used to Identify Novel Co... -
Unchecked Ki = 14000.0 nM 4.85 Enzymatic activity was determined 6317859
No relevant target IC50 = 52095.0 nM 4.28 PubChem BioAssay. Counterscreen for inhibitors of RecBCD: Absorbance-based cell-... -
Endothelin-1 receptor IC50 = 69000.0 nM 4.16 Inhibitory concentration against Endothelin A receptor 14998318
Endothelin-1 receptor IC50 = 69000.0 nM 4.16 Antagonism of [125 I]ET-1 binding to the rat endothelin receptor in vascular smo... 7731020
Unchecked IC50 = 75908.0 nM 4.12 PubChem BioAssay. Absorbance-based bacterial cell-based high throughput dose res... -
Protein arginine N-methyltransferase 6 IC50 = 430000.0 nM 3.37 Inhibition of N-terminal hexa-His tagged human PRMT6 expressed in Sf9 cells usin... 26824386

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 436
- 10.1007/s00044-012-0014-1 Mus musculus 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
36518695 10.1021/acsmedchemlett.2c00429 No relevant target 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18725450 10.1128/aac.00245-08 Pasteurella multocida 7
22365879 10.1016/j.ejmech.2012.01.060 Mycobacterium kansasii 6
34119615 10.1016/j.bmcl.2021.128198 Staphylococcus aureus 5
36623329 10.1016/j.ejmech.2023.115088 Staphylococcus aureus 4
22365879 10.1016/j.ejmech.2012.01.060 Staphylococcus aureus 4
22365879 10.1016/j.ejmech.2012.01.060 Unchecked 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
26833242 10.1016/j.bmc.2016.01.041 Staphylococcus aureus 4
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
36518695 10.1021/acsmedchemlett.2c00429 UDP-N-acetylglucosamine 1-carboxyvinyltransferase 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
26833242 10.1016/j.bmc.2016.01.041 Proteus sp. 3
22365879 10.1016/j.ejmech.2012.01.060 Mycobacterium tuberculosis 3
26833242 10.1016/j.bmc.2016.01.041 Escherichia coli 3
35314326 10.1016/j.bmcl.2022.128695 Staphylococcus aureus 3

Data from ChEMBL 36 via Core Engine