sulfanilamide   Click here for help

GtoPdb Ligand ID: 12631

Synonyms: AVC® | sulphanilamide
Approved drug PDB Ligand
sulfanilamide is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Sulfanilamide is sulfonamide antimicrobial compound. It was first synthesized in 1908, but it was not until the 1930s that its antibacterial activity was discovered [3-4].

sulfanilamide 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 1
Topological polar surface area 94.56
Molecular weight 172.21
XLogP -1.26
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 C1=C(C=CC(=C1)S(=O)(=O)N)N
Isomeric SMILES C1=CC(=CC=C1N)S(=O)(=O)N
InChI InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
InChI Key FDDDEECHVMSUSB-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/)
No information available.
Summary of Clinical Use Click here for help
Sulfanilamide is used as a topical formulation to treat vulvovaginitis caused by Candida albicans. It was marketed in the US (under the trade name AVC®:) but has been discontinued. The drug is not approved by the EMA, but individual European agencies have authorised its use.
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].
External links Click here for help
For extended ADME data see the following:

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