Stereochemistry | ACHIRAL |
Molecular Formula | C10H10N4O2S |
Molecular Weight | 250.277 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC2=NC=CC=N2
InChI
InChIKey=SEEPANYCNGTZFQ-UHFFFAOYSA-N
InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
Sulfadiazine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus. Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid. Used for the treatment of rheumatic fever and meningococcal meningitis.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as perpetrator
Drug as victim
Sourcing
PubMed
Patents
Sample Use Guides
Usual Adult Dose for Toxoplasmosis
Toxoplasmic encephalitis:
Initial dose: Pyrimethamine 200 mg orally once
Maintenance dose:
<60 kg: Sulfadiazine 1 g orally every 6 hours plus pyrimethamine 50 mg orally once a day.
>=60 kg: Sulfadiazine 1500 mg orally every 6 hours plus pyrimethamine 75 mg orally once a day.
In addition, leucovorin 10 to 20 mg/day orally (may increase up to 50 mg/day).
Route of Administration:
Oral