mafenide   Click here for help

GtoPdb Ligand ID: 12697

Synonyms: homosulfanilamide | Sulfamylon®
Approved drug PDB Ligand
mafenide is an approved drug (FDA (1969))
Compound class: Synthetic organic
Comment: Mafenide is a topically applied sulfonamide antibacterial compound, used in the treatment of severe burn wounds [1-2].
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 2
Topological polar surface area 94.56
Molecular weight 186.23
XLogP -1.69
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)CN
Isomeric SMILES C1=CC(=CC=C1CN)S(=O)(=O)N
InChI InChI=1S/C7H10N2O2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,5,8H2,(H2,9,10,11)
InChI Key TYMRLRRVMHJFTF-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 (1969)
IUPAC Name Click here for help
4-(Aminomethyl)benzenesulfonamide
International Nonproprietary Names Click here for help
INN number INN
2393 mafenide
Synonyms Click here for help
homosulfanilamide | Sulfamylon®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Mafenide
Other databases
BindingDB Ligand 10860
CAS Registry No. 138-39-6 (source: Scifinder)
ChEBI CHEBI:6633
ChEMBL Ligand CHEMBL419
DrugBank Ligand DB06795
DrugCentral Ligand 1624
GtoPdb PubChem SID 483123245
PubChem CID 3998
RCSB PDB Ligand 6LH
Search Google for chemical match using the InChIKey TYMRLRRVMHJFTF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone TYMRLRRVMHJFTF
Search PubMed clinical trials mafenide
Search PubMed titles mafenide
Search PubMed titles/abstracts mafenide
UniChem Compound Search for chemical match using the InChIKey TYMRLRRVMHJFTF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey TYMRLRRVMHJFTF-UHFFFAOYSA-N