U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C10H10N4O2S
Molecular Weight 250.277
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[New trends in ocular toxoplasmosis--the review].
2001
Flamazine is not a debriding agent.
2001 Aug 9-Sep 12
[Drug hypersensitivity syndrome rapidly resolving after human immunoglobulin infusion].
2001 Dec
Bullous eruptions caused by extravasation of mannitol--a case report.
2001 Dec
Efficacy of antiadhesive, antibiotic and antiseptic coatings in preventing catheter-related infections: review.
2001 Dec
Matrix solid-phase dispersion extraction and high-performance liquid chromatographic determination of residual sulfonamides in chicken.
2001 Dec 7
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Management of pressure ulcers.
2001 Nov
Safety and efficacy of an improved antiseptic catheter impregnated intraluminally with chlorhexidine.
2001 Nov-Dec
A novel kind of antitumour drugs using sulfonamide as parent compound.
2001 Nov-Dec
In vitro and in vivo efficacy of catheters impregnated with antiseptics or antibiotics: evaluation of the risk of bacterial resistance to the antimicrobials in the catheters.
2001 Oct
The beneficial toxicity paradox of antimicrobials in leg ulcer healing impaired by a polymicrobial flora: a proof-of-concept study.
2002
Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.
2002
[A case of primary pyoderma-like aspergillosis occurring in a patient with a cervical spinal cord injury].
2002
Submaxillary adenopathy as sole manifestation of toxoplasmosis: case report and literature review.
2002 Apr
Prevalence of moderate penicillin resistant invasive Neisseria meningitidis infection in Scotland, 1994-9.
2002 Apr
Transfer and distribution profiles of dietary sulphonamides in the tissues of the laying hen.
2002 Apr
Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry.
2002 Apr 5
New simple liquid chromatographic method for the determination of trimethoprim, sulfadiazine and N4-acetylsulfadiazine in plasma of broilers.
2002 Apr 5
Outbreak of serogroup W135 meningococcal disease after the Hajj pilgrimage, Europe, 2000.
2002 Aug
[Increased serum and urinary levels of silver during treatment with topical silver sulfadiazine].
2002 Feb
[Congenital toxoplasmosis: prevention in the pregnant woman and management of the neonate].
2002 Feb
Comparison of propolis skin cream to silver sulfadiazine: a naturopathic alternative to antibiotics in treatment of minor burns.
2002 Feb
Deep partial thickness burn after contact with a Meal Ready-To-Eat heater.
2002 Feb
Effect of sulphadiazine and trimethoprim on the immune response of rainbow trout (Oncorhynchus mykiss).
2002 Feb
[Treatment of subclinical congenital toxoplasmosis by sulfadiazine and pyrimethamine continuously during 1 year: apropos of 46 cases].
2002 Jan
Effects of silver sulphadiazine on the production of exoproteins by Staphylococcus aureus.
2002 Jan
Antimicrobial-impregnated central venous catheters.
2002 Jan
Evaluation of an antimicrobial-impregnated continuous ambulatory peritoneal dialysis catheter for infection control in rats.
2002 Jan
Atypical anterior optic neuropathy caused by toxoplasmosis.
2002 Jan
Complete osseous regeneration of a large skull defect in a patient with cutis aplasia: a conservative approach.
2002 Jul
An update on current practices in the management of ocular toxoplasmosis.
2002 Jul
A prospective, randomized trial of pyrimethamine and azithromycin vs pyrimethamine and sulfadiazine for the treatment of ocular toxoplasmosis.
2002 Jul
An infection-preventing bilayered collagen membrane containing antibiotic-loaded hyaluronan microparticles: physical and biological properties.
2002 Jul
The effectiveness of processed grapefruit-seed extract as an antibacterial agent: I. An in vitro agar assay.
2002 Jun
Anal canal amputation and necrosis of the anal sphinchter due to electric current injury.
2002 Jun
Laminin modified infection-preventing collagen membrane containing silver sulfadiazine-hyaluronan microparticles.
2002 Jun
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.
2002 Jun
Silver-coated endotracheal tubes associated with reduced bacterial burden in the lungs of mechanically ventilated dogs.
2002 Mar
Is a silver coating a silver lining?
2002 Mar
Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.
2002 Mar
Control of wound infections using a bilayer chitosan wound dressing with sustainable antibiotic delivery.
2002 Mar 5
[Topical agents used in the treatment of burns].
2002 Mar-Apr
[Glanders--a potential disease for biological warfare in humans and animals].
2002 May
Folate deficiency during treatment with orally administered folic acid, sulphadiazine and pyrimethamine in a horse with suspected equine protozoal myeloencephalitis (EPM).
2002 May
Silver. 2: Toxicity in mammals and how its products aid wound repair.
2002 May
Confocal laser microscopic observation of glycocalyx production by Staphylococcus aureus in vitro.
2002 May
Unsuspected Toxoplasma gondii empyema in a bone marrow transplant recipient.
2002 May 1
Randomized phase II trial of atovaquone with pyrimethamine or sulfadiazine for treatment of toxoplasmic encephalitis in patients with acquired immunodeficiency syndrome: ACTG 237/ANRS 039 Study. AIDS Clinical Trials Group 237/Agence Nationale de Recherche sur le SIDA, Essai 039.
2002 May 1
Effect of sulfadiazine and pyrimethamine on selected physiologic and performance parameters in athletically conditioned thoroughbred horses during an incremental exercise stress test.
2002 Spring
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
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:46:51 UTC 2019
Edited
by admin
on Mon Oct 21 19:46:51 UTC 2019
Record UNII
0N7609K889
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY