sulfadimethoxine   Click here for help

GtoPdb Ligand ID: 12638

Synonyms: Albon® (veterinary) | sulfadimethoxydiazine | sulphadimethoxine
Approved drug
sulfadimethoxine is an approved drug (FDA (1958))
Compound class: Synthetic organic
Comment: Sulfadimethoxine 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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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 8
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 123.75
Molecular weight 310.33
XLogP -0.83
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=CC(=NC(=N1)OC)NS(=O)(=O)C2=CC=C(C=C2)N
Isomeric SMILES COC1=NC(=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N)OC
InChI InChI=1S/C12H14N4O4S/c1-19-11-7-10(14-12(15-11)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
InChI Key ZZORFUFYDOWNEF-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
The US FDA has withdrawn all drug products containing sulfadimethoxine from the market for reasons of safety or effectiveness [3]. There is no information regarding approval for clinical use of this drug on the European Medicines Agency website but it may still be approved for use in other countries.
Principal use is in veterinary practice, where it is used to treat a wide range of sulfadimethoxine-sensitive bacterial infections and bacterial enteritis associated with coccidiosis.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Sulfonamides are structural analogues of 4-aminobenzoic acid (pABA) an intermediate in the de novo synthesis of folate by some prokaryotes, lower eukaryotes and plants [2]. The antibacterial MMOA is competitive inhibition of bacterial dihydropteroate synthase (DHPS) resulting in a block of folate biosynthesis [1].