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
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
PubMed
Title | Date | PubMed |
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[New trends in ocular toxoplasmosis--the review]. | 2001 |
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A case of vaginal argyrosis: all that glistens isn't gold. | 2001 Aug |
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Two episodes of life-threatening anaphylaxis in the same patient to a chlorhexidine-sulphadiazine-coated central venous catheter. | 2001 Aug |
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Flamazine is not a debriding agent. | 2001 Aug 9-Sep 12 |
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[Drug hypersensitivity syndrome rapidly resolving after human immunoglobulin infusion]. | 2001 Dec |
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Bullous eruptions caused by extravasation of mannitol--a case report. | 2001 Dec |
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Enhanced anti-Shigella activity of erythromycin supplemented with sulfadiazine. | 2001 Dec |
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Pentadecapeptide BPC 157 cream improves burn-wound healing and attenuates burn-gastric lesions in mice. | 2001 Dec |
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Development of an artificial dermis preparation capable of silver sulfadiazine release. | 2001 Dec 5 |
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Matrix solid-phase dispersion extraction and high-performance liquid chromatographic determination of residual sulfonamides in chicken. | 2001 Dec 7 |
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Inhibition of aerobic growth and nitrification of bacteria in sewage sludge by antibacterial agents. | 2001 May |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Management of pressure ulcers. | 2001 Nov |
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Clinical microbiological case: visual problems in an HIV-positive patient. | 2001 Nov |
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Winston Churchill and M & B. | 2001 Nov |
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Myelitis and ascending flaccid paralysis due to congenital toxoplasmosis. | 2001 Nov 15 |
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Safety and efficacy of an improved antiseptic catheter impregnated intraluminally with chlorhexidine. | 2001 Nov-Dec |
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A novel kind of antitumour drugs using sulfonamide as parent compound. | 2001 Nov-Dec |
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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 |
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Myth: silver sulfadiazine is the best treatment for minor burns. | 2001 Sep |
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Suspected protozoal myeloencephalitis in a two-month-old colt. | 2001 Sep 1 |
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Phase II study assessing the effectiveness of Biafine cream as a prophylactic agent for radiation-induced acute skin toxicity to the breast in women undergoing radiotherapy with concomitant CMF chemotherapy. | 2001 Sep 1 |
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The beneficial toxicity paradox of antimicrobials in leg ulcer healing impaired by a polymicrobial flora: a proof-of-concept study. | 2002 |
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Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry. | 2002 |
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[A case of primary pyoderma-like aspergillosis occurring in a patient with a cervical spinal cord injury]. | 2002 |
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Submaxillary adenopathy as sole manifestation of toxoplasmosis: case report and literature review. | 2002 Apr |
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Prevalence of moderate penicillin resistant invasive Neisseria meningitidis infection in Scotland, 1994-9. | 2002 Apr |
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Transfer and distribution profiles of dietary sulphonamides in the tissues of the laying hen. | 2002 Apr |
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New simple liquid chromatographic method for the determination of trimethoprim, sulfadiazine and N4-acetylsulfadiazine in plasma of broilers. | 2002 Apr 5 |
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[Increased serum and urinary levels of silver during treatment with topical silver sulfadiazine]. | 2002 Feb |
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[Congenital toxoplasmosis: prevention in the pregnant woman and management of the neonate]. | 2002 Feb |
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Comparison of propolis skin cream to silver sulfadiazine: a naturopathic alternative to antibiotics in treatment of minor burns. | 2002 Feb |
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Deep partial thickness burn after contact with a Meal Ready-To-Eat heater. | 2002 Feb |
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Effect of sulphadiazine and trimethoprim on the immune response of rainbow trout (Oncorhynchus mykiss). | 2002 Feb |
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[Treatment of subclinical congenital toxoplasmosis by sulfadiazine and pyrimethamine continuously during 1 year: apropos of 46 cases]. | 2002 Jan |
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Effects of silver sulphadiazine on the production of exoproteins by Staphylococcus aureus. | 2002 Jan |
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Antimicrobial-impregnated central venous catheters. | 2002 Jan |
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Evaluation of an antimicrobial-impregnated continuous ambulatory peritoneal dialysis catheter for infection control in rats. | 2002 Jan |
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Atypical anterior optic neuropathy caused by toxoplasmosis. | 2002 Jan |
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The effectiveness of processed grapefruit-seed extract as an antibacterial agent: I. An in vitro agar assay. | 2002 Jun |
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Anal canal amputation and necrosis of the anal sphinchter due to electric current injury. | 2002 Jun |
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Silver-coated endotracheal tubes associated with reduced bacterial burden in the lungs of mechanically ventilated dogs. | 2002 Mar |
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Is a silver coating a silver lining? | 2002 Mar |
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Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives. | 2002 Mar |
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Control of wound infections using a bilayer chitosan wound dressing with sustainable antibiotic delivery. | 2002 Mar 5 |
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[Topical agents used in the treatment of burns]. | 2002 Mar-Apr |
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[Glanders--a potential disease for biological warfare in humans and animals]. | 2002 May |
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Folate deficiency during treatment with orally administered folic acid, sulphadiazine and pyrimethamine in a horse with suspected equine protozoal myeloencephalitis (EPM). | 2002 May |
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Confocal laser microscopic observation of glycocalyx production by Staphylococcus aureus in vitro. | 2002 May |
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Unsuspected Toxoplasma gondii empyema in a bone marrow transplant recipient. | 2002 May 1 |
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
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QJ01EW10
Created by
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LIVERTOX |
906
Created by
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Code System | Code | Type | Description | ||
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M10305
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PRIMARY | Merck Index | ||
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D013411
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SULFADIAZINE
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CHEMBL439
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SUB10695MIG
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68-35-9
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5215
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PRIMARY | |||
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C29468
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421
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200-685-8
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10171
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68-35-9
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DB00359
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)