sulfametoxydiazine   Click here for help

GtoPdb Ligand ID: 12641

Synonyms: sulfameter | sulfamethoxydiazine | Sulla®
Approved drug
sulfametoxydiazine is an approved drug (FDA (1966))
Compound class: Synthetic organic
Comment: Sulfametoxydiazine (USAN: sulfameter) is a sulfonamide antibacterial compound. This class of compounds are competitive inhibitors of bacterial dihydropteroate synthase (DHPS), an enzyme in the pathway which generates the folic acid that is essential for bacterial growth.
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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Click here for structure editor
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 CDK toolkit. 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 7
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 114.52
Molecular weight 280.3
XLogP -1.23
No. Lipinski's rules broken 0
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.

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Canonical SMILES COC1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
Isomeric SMILES COC1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI InChI=1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
InChI Key GPTONYMQFTZPKC-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1966))
IUPAC Name Click here for help
4-amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide
International Nonproprietary Names Click here for help
INN number INN
1335 sulfametoxydiazine
Synonyms Click here for help
sulfameter | sulfamethoxydiazine | Sulla®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sulfameter, Sulfamethoxydiazine
Other databases
CAS Registry No. 651-06-9 (source: Scifinder)
ChEBI CHEBI:53727
ChEMBL Ligand CHEMBL1200359
DrugBank Ligand DB06821
DrugCentral Ligand 2511
GtoPdb PubChem SID 479821431
PubChem CID 5326
Search Google for chemical match using the InChIKey GPTONYMQFTZPKC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GPTONYMQFTZPKC
Search PubMed clinical trials sulfametoxydiazine
Search PubMed titles sulfametoxydiazine
Search PubMed titles/abstracts sulfametoxydiazine
UniChem Compound Search for chemical match using the InChIKey GPTONYMQFTZPKC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GPTONYMQFTZPKC-UHFFFAOYSA-N