sulfamethoxazole   Click here for help

GtoPdb Ligand ID: 10933

Synonyms: Gantanol® | RO 4-2130 | RO-42130 | SMX | STX-608
Approved drug PDB Ligand
sulfamethoxazole is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Sulfamethoxazole is a sulfonamide antibacterial that has bacteriostatic activity. It inhibits the bacterial dihydropteroate synthase pathway which generates the folic acid that is essential for bacterial growth. It is active against Gram-negative and Gram-positive bacteria including Listeria monocytogenes and E. coli.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 106.6
Molecular weight 253.05
XLogP 1.18
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES Nc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
Isomeric SMILES Nc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
InChI InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChI Key JLKIGFTWXXRPMT-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
Approved drug? Yes. FDA (1965)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
International Nonproprietary Names Click here for help
INN number INN
1386 sulfamethoxazole
Synonyms Click here for help
Gantanol® | RO 4-2130 | RO-42130 | SMX | STX-608
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sulfamethoxazole
Other databases
CAS Registry No. 723-46-6 (source: PubChem)
ChEMBL Ligand CHEMBL443
DrugBank Ligand DB01015
DrugCentral Ligand 2514
GtoPdb PubChem SID 405560374
PubChem CID 5329
RCSB PDB Ligand 08D
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UniChem Compound Search for chemical match using the InChIKey JLKIGFTWXXRPMT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JLKIGFTWXXRPMT-UHFFFAOYSA-N

Product suppliers

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MedChemExpress
Sulfamethoxazole (links to external site)
Cat. No. HY-B0322
Sulfamethoxazole (Standard) (links to external site)
Cat. No. HY-B0322R