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Details

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
Structure of SULFADIAZINE

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)

HIDE SMILES / InChI

Description

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

Targets

Primary TargetPharmacologyConditionPotency
21.0 µM [IC50]
41.2 µM [IC50]
4.2 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Sulfadiazine
Curative
Sulfadiazine
Curative
Sulfadiazine

Cmax

ValueDoseCo-administeredAnalytePopulation
84.9 μg/mL
2 g 2 times / day steady-state, oral
SULFADIAZINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.247 μg × h/mL
2 g 2 times / day steady-state, oral
SULFADIAZINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.9 h
2 g 2 times / day steady-state, oral
SULFADIAZINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Sulfadiazine inhibited Pseudomonas aeruginosa with MIC 256 ug/mL