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Details

Stereochemistry ACHIRAL
Molecular Formula C10H10N4O2S
Molecular Weight 250.277
Optical Activity UNSPECIFIED
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

PubMed

PubMed

TitleDatePubMed
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Patents

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
Name Type Language
SULFADIAZINE
EP   GREEN BOOK   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
SULFADIAZINE [ORANGE BOOK]
Common Name English
SDZ
Common Name English
SULFADIAZINE [EP]
Common Name English
SULFADIAZINE COMPONENT OF SULFONAMIDES DUPLEX
Common Name English
SULFADIAZINE [INN]
Common Name English
SULFADIAZINE [USP]
Common Name English
NEOTRIZINE COMPONENT SULFADIAZINE
Common Name English
SULFACOMBIN
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-PYRIMIDINYL-
Systematic Name English
N(SUP 1)-2-PYRIMIDINYLSULFANILAMIDE
Systematic Name English
SULFADIAZINE COMPONENT OF LANTRISUL
Common Name English
SULFADIAZINE [GREEN BOOK]
Common Name English
SULFADIAZINE COMPONENT OF NEOTRIZINE
Common Name English
SULFADIAZINE [JAN]
Common Name English
SULFADIAZINE COMPONENT OF TRIPLE SULFOID
Common Name English
TRIPLE SULFOID COMPONENT SULFADIAZINE
Common Name English
SULFADIAZINE [WHO-DD]
Common Name English
TERFONYL COMPONENT SULFADIAZINE
Common Name English
COCO-DIAZINE
Brand Name English
SULFADIAZINE COMPONENT OF TERFONYL
Common Name English
SULFALOID COMPONENT SULFADIAZINE
Common Name English
SULFONAMIDES DUPLEX COMPONENT SULFADIAZINE
Common Name English
SULFOSE COMPONENT SULFADIAZINE
Common Name English
SULPHADIAZINE
Common Name English
LANTRISUL COMPONENT SULFADIAZINE
Common Name English
SULFADIAZINE COMPONENT OF SULFOSE
Common Name English
SULFADIAZINE [VANDF]
Common Name English
NSC-35600
Code English
SULFADIAZINE COMPONENT OF SULFALOID
Common Name English
SULFADIAZINE [MART.]
Common Name English
SULFADIMIDINE IMPURITY B [EP]
Common Name English
SULFADIAZINE [USP-RS]
Common Name English
SULFADIAZINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01EW10
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
LIVERTOX 906
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
WHO-ATC J01EC02
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
CFR 21 CFR 520.2611
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
WHO-ATC J01EE06
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
CFR 21 CFR 520.2610
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
WHO-VATC QJ01EQ10
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
CFR 21 CFR 520.2215
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
CFR 21 CFR 520.2613
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
CFR 21 CFR 520.2612
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
FDA ORPHAN DRUG 78093
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
WHO-ATC J01EE02
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
WHO-VATC QJ51RE01
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.5.4
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
CFR 21 CFR 522.2610
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
NDF-RT N0000175503
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
NCI_THESAURUS C29739
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
Code System Code Type Description
MERCK INDEX
M10305
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY Merck Index
MESH
D013411
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
WIKIPEDIA
SULFADIAZINE
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
ChEMBL
CHEMBL439
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
EVMPD
SUB10695MIG
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
CAS
68-35-9
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
PUBCHEM
5215
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
NCI_THESAURUS
C29468
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
INN
421
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-685-8
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
RXCUI
10171
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY RxNorm
EPA CompTox
68-35-9
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY
DRUG BANK
DB00359
Created by admin on Mon Oct 21 19:46:51 UTC 2019 , Edited by admin on Mon Oct 21 19:46:51 UTC 2019
PRIMARY