sulfapyridine   Click here for help

GtoPdb Ligand ID: 12698

Synonyms: Dagenan® | M&B 693 | sulphapyridine
Approved drug PDB Ligand
sulfapyridine is an approved drug (FDA (1939))
Compound class: Synthetic organic
Comment: Sulfapyridine is a sulfonamide compound that was used clinically as an antibacterial agent but is now used principally as an anti-inflammatory drug.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 92.93
Molecular weight 249.29
XLogP -0.61
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES C1=CC(=NC=C1)NS(=O)(=O)C2=CC=C(C=C2)N
Isomeric SMILES C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI InChI=1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14)
InChI Key GECHUMIMRBOMGK-UHFFFAOYSA-N
References
1. Achari A, Somers DO, Champness JN, Bryant PK, Rosemond J, Stammers DK. (1997)
Crystal structure of the anti-bacterial sulfonamide drug target dihydropteroate synthase.
Nat Struct Biol, 4 (6): 490-7. [PMID:9187658]
2. Bermingham A, Derrick JP. (2002)
The folic acid biosynthesis pathway in bacteria: evaluation of potential for antibacterial drug discovery.
Bioessays, 24 (7): 637-48. [PMID:12111724]
3. Fry L. (1995)
Dermatitis herpetiformis.
Baillieres Clin Gastroenterol, 9 (2): 371-93. [PMID:7549032]
4. Ovung A, Bhattacharyya J. (2021)
Sulfonamide drugs: structure, antibacterial property, toxicity, and biophysical interactions.
Biophys Rev, 13 (2): 259-272. [PMID:33936318]
5. Paniker U, Levine N. (2001)
Dapsone and sulfapyridine.
Dermatol Clin, 19 (1): 79-86, viii. [PMID:11155588]
6. Tredway JB, Sadusk JF. (1941)
Observations on the Response in Vitro of the Pneumococcus, Staphylococcus, Alpha Hemolytic Streptococcus, and Friedlander's Bacillus to the Sulfonamide Drugs.
Yale J Biol Med, 14 (2): 143-154.1. [PMID:21434003]
7. Whitby LEH. (1938)
CHEMOTHERAPY OF PNEUMOCOCCAL AND OTHER INFECTIONS: WITH 2-(p-AMINOBENZENESULPHONAMIDO) PYRIDINE.
The Lancet, 231 (5987): 1210-1212. DOI: 10.1016/S0140-6736(00)89787-1