sulfamerazine   Click here for help

GtoPdb Ligand ID: 12640

Synonyms: 2-sulfanilamido-4-methylpyrimidine | sulfamethyldiazine | sulphamerazine
Approved drug
sulfamerazine is an approved drug (FDA (1949))
Compound class: Synthetic organic
Comment: Sulfamerazine is a sulfonamide antibacterial compound [4]. This class of compounds are competitive inhibitors of bacterial dihydropteroate synthase (DHPS), an enzyme in the pathway which generates the folic acid that is essential for bacterial growth.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 105.29
Molecular weight 264.31
XLogP -1.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC1=CC=NC(=N1)NS(=O)(=O)C2=CC=C(C=C2)N
Isomeric SMILES CC1=NC(=NC=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
InChI Key QPPBRPIAZZHUNT-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. Ovung A, Bhattacharyya J. (2021)
Sulfonamide drugs: structure, antibacterial property, toxicity, and biophysical interactions.
Biophys Rev, 13 (2): 259-272. [PMID:33936318]
4. Roblin RO, Williams JH, Winnek PS, English JP. (1940)
Chemotherapy. II. Some sulfanilamido heterocycles.
J. Am. Chem. Soc., 62: 2002-5. DOI: 10.1021/ja01865a027