prontosil   Click here for help

GtoPdb Ligand ID: 12743

Synonyms: prontosil red | prontosil rubrum | sulfamidochrysoidine
Compound class: Synthetic organic
Comment: Prontosil is a sulfonamide antibacterial compound and the first drug available commercially for the treatment of bacterial infections. It is a prodrug of sulfanilamide. The antibacterial properties of prontosil were first identified by Gerhard Domagk (Bayer Laboratories) in the early 1930s, leading to him being awarded the 1939 Nobel Prize in Physiology or Medicine [5].
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 7
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 145.3
Molecular weight 291.33
XLogP -0.19
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=C(C(=C1)N=NC2=CC=C(C=C2)S(=O)(=O)N)N)N
Isomeric SMILES C1=CC(=CC=C1N=NC2=C(C=C(C=C2)N)N)S(=O)(=O)N
InChI InChI=1S/C12H13N5O2S/c13-8-1-6-12(11(14)7-8)17-16-9-2-4-10(5-3-9)20(15,18)19/h1-7H,13-14H2,(H2,15,18,19)
InChI Key ABBQGOCHXSPKHJ-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.
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].