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.

sulfamethoxazole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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/)

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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)
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
Search Google for chemical match using the InChIKey JLKIGFTWXXRPMT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JLKIGFTWXXRPMT
Search PubMed clinical trials sulfamethoxazole
Search PubMed titles sulfamethoxazole
Search PubMed titles/abstracts sulfamethoxazole
UniChem Compound Search for chemical match using the InChIKey JLKIGFTWXXRPMT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JLKIGFTWXXRPMT-UHFFFAOYSA-N

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