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Compound Detail

CHEMBL443

SULFAMETHOXAZOLE
💊 Approved Drug
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💊 Approved Drug
Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL443
Name SULFAMETHOXAZOLE
Phase Approved
Structure Type MOL
InChI Key JLKIGFTWXXRPMT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acetylsulfamethoxazole Gantanol Gantanol-ds NSC-147832 RO 4-2130 RO-4-2130 Sinomin STX-608 Sulfamethoxazole Sulfamethoxazole component of azo gantanol Sulfamethoxazole component of bactrim Sulfamethoxazole component of bactrim ds +15 more
6
Targets
14
Activities
3
Assay Types
21
PK Parameters
20
Publications
27
Known Names
20
Indications
1
Mechanisms

Molecular Properties

253.3
MW (Da)
1.37
ALogP
5
HBA
2
HBD
98.2
PSA (Ų)
0.80
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1973
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem sulfa-
USAN Year 1962

Extended Properties

Molecular Formula C10H11N3O3S
MW 253.28
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -2.12

Mechanism of Action

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

Indications

Bacterial Infections Infections Pneumonia, Pneumocystis Urinary Tract Infections Abscess HIV Infections Idiopathic Pulmonary Fibrosis Malaria Measles Pneumonia Pyelonephritis Sepsis Staphylococcal Infections Toxoplasmosis, Ocular Tuberculosis Cystic Fibrosis Dermatitis Diabetes Mellitus, Type 1 Eczema Lymphoma, AIDS-Related

ATC Classification

J01EC01
sulfamethoxazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 12 meas. best 7.0
Kd 1 meas. best 6.24
Ki 1 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 8.0 8.0 10.1 1
Dihydrofolate reductase
CHEMBL1926
 IC50 7.0 7.0 100.0 1
Human immunodeficiency virus type 1 protease
CHEMBL243
 Kd 6.24 6.24 577.0 1
Endothelin-1 receptor
CHEMBL4566
 IC50 5.4 5.4 4000.0 2
Dihydropteroate synthase
CHEMBL4032
 IC50 5.33 5.33 4700.0 1
Unchecked
CHEMBL612545
 IC50 4.54 4.3367 29167.0 3
No relevant target
CHEMBL2362975
 IC50 4.27 4.27 54149.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.36 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.36 mL.min-1.kg-1 Homo sapiens
CL 0.36 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 0.000213 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 0.213 uL/min Homo sapiens
Cmax 157927.98 nM Homo sapiens
Compound Recovery 84.5 % Homo sapiens
Css 68.0 mcg/mL Homo sapiens
Css 68.0 mcg/mL Homo sapiens
Css min 57.4 mcg/mL Homo sapiens
F 80.0 % Homo sapiens
Fu 0.23 - Homo sapiens
Fu 0.23 - Homo sapiens
MRT 14.0 hr Homo sapiens
T1/2 9.8 hr Homo sapiens
T1/2 10.0 hr Homo sapiens
Tmax 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus type 1 protease Ki = 10.1 nM 8.0 Inhibition constant for human immunodeficiency virus type 1 protease 15537350
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Inhibitory activity against dihydrofolate reductase in Pneumocystis carinii in t... 7490723
Human immunodeficiency virus type 1 protease Kd = 577.0 nM 6.24 Binding affinity for human immunodeficiency virus type 1 protease 15537350
Endothelin-1 receptor IC50 = 4000.0 nM 5.4 Antagonism of [125 I]ET-1 binding to the rat endothelin receptor in vascular smo... 7731020
Endothelin-1 receptor IC50 = 4000.0 nM 5.4 Inhibition of [125I]endothelin-l binding to endothelin A receptor of rat thoraci... 7861414
Dihydropteroate synthase IC50 = 4700.0 nM 5.33 In vitro inhibition of dihydropteroate synthase from Escherichia coli. 3906132
Unchecked IC50 = 29167.0 nM 4.54 PUBCHEM_BIOASSAY: Counterscreen for AddAB inhibitors: absorbance-based bacterial... -
Unchecked IC50 = 36211.0 nM 4.44 PUBCHEM_BIOASSAY: Absorbance-based bacterial cell-based high throughput dose res... -
No relevant target IC50 = 54149.0 nM 4.27 PubChem BioAssay. Counterscreen for inhibitors of RecBCD: Absorbance-based cell-... -
Unchecked IC50 = 94317.0 nM 4.03 PubChem BioAssay. Absorbance-based bacterial cell-based high throughput dose res... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
29784273 10.1016/j.bmc.2018.05.019 Staphylococcus aureus 27
18809939 10.1128/aac.00830-08 Enterobacter cloacae 14
20585113 10.1128/aac.01783-09 Escherichia coli 14
19528282 10.1128/aac.01522-08 Pasteurella multocida 14
18809939 10.1128/aac.00830-08 Klebsiella pneumoniae 12
18809939 10.1128/aac.00830-08 Citrobacter freundii 10
18070962 10.1128/aac.00375-07 Escherichia coli 9
18936192 10.1128/aac.00886-08 Escherichia coli 8
20070106 10.1021/jm901371v Homo sapiens 8
1560438 10.1021/jm00085a012 Rattus norvegicus 7
17724159 10.1128/aac.00616-07 Escherichia coli 7
38466654 10.1021/acs.jmedchem.3c02355 Staphylococcus aureus 6
22365879 10.1016/j.ejmech.2012.01.060 Mycobacterium kansasii 6
18644958 10.1128/aac.00638-08 Escherichia coli 6
18809939 10.1128/aac.00830-08 Escherichia coli 5
19901088 10.1128/aac.00310-09 Escherichia coli 5
19687243 10.1128/aac.00688-09 Escherichia coli 5
32298876 10.1016/j.ejmech.2020.112268 Pseudomonas aeruginosa 5
15537350 10.1021/jm0499110 Human immunodeficiency virus type 1 protease 4

Data from ChEMBL 36 via Core Engine