sulfadimidine   Click here for help

GtoPdb Ligand ID: 12642

Synonyms: sulfamethazine
Approved drug
sulfadimidine is an approved drug (FDA (1949))
Compound class: Synthetic organic
Comment: Sulfadimidine (sulfamethazine) 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.

sulfadimidine 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 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 105.29
Molecular weight 278.33
XLogP -0.73
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 CC1=NC(=NC(=C1)C)NS(=O)(=O)C2=CC=C(C=C2)N
Isomeric SMILES CC1=CC(=NC(=N1)NS(=O)(=O)C2=CC=C(C=C2)N)C
InChI InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
InChI Key ASWVTGNCAZCNNR-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 (1949)
IUPAC Name Click here for help
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
International Nonproprietary Names Click here for help
INN number INN
1068 sulfadimidine
Synonyms Click here for help
sulfamethazine
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sulfamethazine
Other databases
CAS Registry No. 57-68-1 (source: Scifinder)
ChEBI CHEBI:102265
ChEMBL Ligand CHEMBL446
DrugBank Ligand DB01582
DrugCentral Ligand 2502
GtoPdb PubChem SID 479821432
PubChem CID 5327
Search Google for chemical match using the InChIKey ASWVTGNCAZCNNR-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ASWVTGNCAZCNNR
Search PubMed clinical trials sulfadimidine
Search PubMed titles sulfadimidine
Search PubMed titles/abstracts sulfadimidine
UniChem Compound Search for chemical match using the InChIKey ASWVTGNCAZCNNR-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ASWVTGNCAZCNNR-UHFFFAOYSA-N

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MedChemExpress
Sulfamethazine (links to external site)
Cat. No. HY-B0035
Sulfamethazine (Standard) (links to external site)
Cat. No. HY-B0035R