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Details

Stereochemistry ACHIRAL
Molecular Formula 2C10H9N4O2S.Zn
Molecular Weight 563.947
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFADIAZINE ZINC

SMILES

[Zn++].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=NC=CC=N2.NC3=CC=C(C=C3)S(=O)(=O)[N-]C4=NC=CC=N4

InChI

InChIKey=RXXROIWDLGTUIN-UHFFFAOYSA-N
InChI=1S/2C10H9N4O2S.Zn/c2*11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h2*1-7H,11H2;/q2*-1;+2

HIDE SMILES / InChI

Molecular Formula Zn
Molecular Weight 65.409
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Pharmacokinetics and bioavailability of sulfadiazine and trimethoprim (trimazin 30%) after oral administration in non-fasted young pigs.
2001 Aug
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
Enhanced anti-Shigella activity of erythromycin supplemented with sulfadiazine.
2001 Dec
Pentadecapeptide BPC 157 cream improves burn-wound healing and attenuates burn-gastric lesions in mice.
2001 Dec
Development of an artificial dermis preparation capable of silver sulfadiazine release.
2001 Dec 5
Inhibition of aerobic growth and nitrification of bacteria in sewage sludge by antibacterial agents.
2001 May
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Management of pressure ulcers.
2001 Nov
Clinical microbiological case: visual problems in an HIV-positive patient.
2001 Nov
Winston Churchill and M & B.
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
Crystalluria with sulphadiazine.
2001 Oct
Myth: silver sulfadiazine is the best treatment for minor burns.
2001 Sep
Suspected protozoal myeloencephalitis in a two-month-old colt.
2001 Sep 1
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
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
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
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
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
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
[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
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
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 Tue Oct 22 00:40:54 UTC 2019
Edited
by admin
on Tue Oct 22 00:40:54 UTC 2019
Record UNII
5FE7HP0JMG
Record Status Validated (UNII)
Record Version
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Name Type Language
SULFADIAZINE ZINC
Common Name English
ZINC SULFADIAZINE [WHO-DD]
Common Name English
ZINC SULFADIAZINE
WHO-DD  
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-PYRIMIDINYL-, ZINC SALT (2:1)
Common Name English
Code System Code Type Description
PUBCHEM
152849
Created by admin on Tue Oct 22 00:40:54 UTC 2019 , Edited by admin on Tue Oct 22 00:40:54 UTC 2019
PRIMARY
CAS
69858-60-2
Created by admin on Tue Oct 22 00:40:54 UTC 2019 , Edited by admin on Tue Oct 22 00:40:54 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY