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Compound Detail

CHEMBL453

SULFISOXAZOLE
💊 Approved Drug
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💊 Approved Drug
Cc1noc(NS(=O)(=O)c2ccc(N)cc2)c1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL453
Name SULFISOXAZOLE
Phase Approved
Structure Type MOL
InChI Key NHUHCSRWZMLRLA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Entusil Eryzole Gantrisin Neazolin NSC-13120 NSC-683536 Pediazole Sosol Soxazole Sulfafurazol Sulfafurazole Sulfalar +4 more
4
Targets
11
Activities
2
Assay Types
11
PK Parameters
20
Publications
16
Known Names
3
Indications
1
Mechanisms

Molecular Properties

267.3
MW (Da)
1.67
ALogP
5
HBA
2
HBD
98.2
PSA (Ų)
0.82
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1971
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Year 1966

Extended Properties

Molecular Formula C11H13N3O3S
MW 267.31
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -1.82

Mechanism of Action

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

Indications

Bacterial Infections Eye Infections Osteomyelitis

ATC Classification

J01EB05
sulfafurazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AB02
sulfafurazole
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 9 meas. best 6.11
Ki 2 meas. best 4.87

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Endothelin-1 receptor
CHEMBL252
 IC50 6.11 5.7375 780.0 4
Endothelin-1 receptor
CHEMBL4566
 IC50 6.11 5.7533 780.0 3
Endothelin-1 receptor
CHEMBL252
 Ki 4.87 4.87 13465.0 1
Endothelin receptor type B
CHEMBL1785
 IC50 4.62 4.62 24000.0 1
Rattus norvegicus
CHEMBL376
 IC50 4.4 4.4 40000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 mL.min-1.g-1 Homo sapiens
F 80.0 % Homo sapiens
Fu 0.079 - Homo sapiens
Fu 0.079 - Homo sapiens
MRT 9.4 hr Homo sapiens
T1/2 7.4 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Endothelin-1 receptor IC50 = 780.0 nM 6.11 Inhibitory concentration against Endothelin A receptor 14998318
Endothelin-1 receptor IC50 = 780.0 nM 6.11 Antagonism of [125 I]ET-1 binding to the rat endothelin receptor in vascular smo... 7731020
Endothelin-1 receptor IC50 = 780.0 nM 6.11 Ability to inhibit [125I]ET1 binding to vascular smooth muscle (vsm)- A10 cells 8308857
Endothelin-1 receptor IC50 = 800.0 nM 6.1 Inhibition of [125I]endothelin-l binding to endothelin A receptor of rat thoraci... 7861414
Endothelin-1 receptor IC50 = 850.0 nM 6.07 Binding affinity against human Endothelin A receptor in TE 671(ATCC# HTB 139) ce... -
Endothelin-1 receptor IC50 = 9000.0 nM 5.05 Displacement of [125 I] ET-1 from rat aortic smooth muscle A7r5 cells transfecte... 10969989
Endothelin-1 receptor Ki = 13465.0 nM 4.87 DRUGMATRIX: Endothelin ETA radioligand binding (ligand: [125I] Endothelin-1) -
Endothelin-1 receptor IC50 = 21880.0 nM 4.66 DRUGMATRIX: Endothelin ETA radioligand binding (ligand: [125I] Endothelin-1) -
Endothelin receptor type B IC50 = 24000.0 nM 4.62 Binding affinity against human Endothelin B receptor in transfected COS 7 cell m... -
Rattus norvegicus IC50 = 40000.0 nM 4.4 Tested for antagonistic activity against ET-1 induced increase in intracellular ... 7731020

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
32220521 10.1016/j.bmc.2020.115444 Unchecked 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL3301361 ADMET 5
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
35314326 10.1016/j.bmcl.2022.128695 Staphylococcus aureus 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
10891117 10.1021/jm0000564 ADMET 2
8308857 10.1021/jm00029a001 Endothelin-1 receptor 2
6864729 10.1021/jm00361a014 Escherichia coli 2
6864729 10.1021/jm00361a014 No relevant target 2
25050881 10.1016/j.ejmech.2014.07.052 Klebsiella pneumoniae 2
25050881 10.1016/j.ejmech.2014.07.052 Aspergillus fumigatus 2
25050881 10.1016/j.ejmech.2014.07.052 Escherichia coli 2
25050881 10.1016/j.ejmech.2014.07.052 Syncephalastrum racemosum 2

Data from ChEMBL 36 via Core Engine