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].
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 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
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 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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
Prodrug prontosil
IUPAC Name Click here for help
4-Aminobenzenesulfonamide
International Nonproprietary Names Click here for help
INN number INN
426 sulfanilamide
Synonyms Click here for help
AVC® | sulphanilamide
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sulfanilamide
Other databases
CAS Registry No. 63-74-1 (source: Scifinder)
ChEBI CHEBI:45373
ChEMBL Ligand CHEMBL21
DrugBank Ligand DB00259
DrugCentral Ligand 2521
GtoPdb PubChem SID 479821421
PubChem CID 5333
RCSB PDB Ligand SAN
Search Google for chemical match using the InChIKey FDDDEECHVMSUSB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone FDDDEECHVMSUSB
Search PubMed clinical trials sulfanilamide
Search PubMed titles sulfanilamide
Search PubMed titles/abstracts sulfanilamide
UniChem Compound Search for chemical match using the InChIKey FDDDEECHVMSUSB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey FDDDEECHVMSUSB-UHFFFAOYSA-N
Wikipedia Sulfanilamide