Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H9N4O2S.Na |
Molecular Weight | 272.259 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=NC=CC=N2
InChI
InChIKey=JLDCNMJPBBKAHH-UHFFFAOYSA-N
InChI=1S/C10H9N4O2S.Na/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h1-7H,11H2;/q-1;+1
DescriptionSources: http://www.drugbank.ca/drugs/DB00359Curator's Comment: Description was created based on several sources, including https://www.drugs.com/dosage/sulfadiazine.html
Sources: http://www.drugbank.ca/drugs/DB00359
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/dosage/sulfadiazine.html
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4722 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18457385 |
21.0 µM [IC50] | ||
Target ID: CHEMBL612888 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18563892 |
41.2 µM [IC50] | ||
Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17719222 |
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Target ID: CHEMBL2013 Sources: http://www.drugbank.ca/drugs/DB00359 |
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Target ID: CHEMBL2364668 Sources: http://www.genome.jp/dbget-bin/www_bget?D00587 |
4.2 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Sulfadiazine Approved UseSulfadiazine tablets USP are indicated in the following conditions:
Chancroid
Trachoma
Inclusion conjunctivitis
Nocardiosis
Urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) in the absence of obstructive uropathy or foreign bodies, when these infections are caused by susceptible strains of the following organisms: Escherichia coli, Klebsiella species, Enterobacter species, Staphylococcus aureus, Proteus mirabilis and P. vulgaris. Sulfadiazine should be used for urinary tract infections only after use of more soluble sulfonamides has been unsuccessful.
Toxoplasmosis encephalitis in patients with and without acquired immunodeficiency syndrome, as adjunctive therapy with pyrimethamine.
Malaria due to chloroquine-resistant strains of Plasmodium falciparum, when used as adjunctive therapy.
Prophylaxis of meningococcal meningitis when sulfonamide-sensitive group A strains are known to prevail in family groups or larger closed populations (the prophylactic usefulness of sulfonamides when group B or C infections are prevalent is not proved and may be harmful in closed population groups).
Meningococcal meningitis, when the organism has been demonstrated to be susceptible.
Acute otitis media due to Haemophilusinfluenzae, when used concomitantly with adequate doses of penicillin.
Prophylaxis against recurrences of rheumatic fever, as an alternative to penicillin.
H. influenzae meningitis, as adjunctive therapy with parental streptomycin. Launch Date1994 |
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Curative | Sulfadiazine Approved UseSulfadiazine tablets USP are indicated in the following conditions:
Chancroid
Trachoma
Inclusion conjunctivitis
Nocardiosis
Urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) in the absence of obstructive uropathy or foreign bodies, when these infections are caused by susceptible strains of the following organisms: Escherichia coli, Klebsiella species, Enterobacter species, Staphylococcus aureus, Proteus mirabilis and P. vulgaris. Sulfadiazine should be used for urinary tract infections only after use of more soluble sulfonamides has been unsuccessful.
Toxoplasmosis encephalitis in patients with and without acquired immunodeficiency syndrome, as adjunctive therapy with pyrimethamine.
Malaria due to chloroquine-resistant strains of Plasmodium falciparum, when used as adjunctive therapy.
Prophylaxis of meningococcal meningitis when sulfonamide-sensitive group A strains are known to prevail in family groups or larger closed populations (the prophylactic usefulness of sulfonamides when group B or C infections are prevalent is not proved and may be harmful in closed population groups).
Meningococcal meningitis, when the organism has been demonstrated to be susceptible.
Acute otitis media due to Haemophilusinfluenzae, when used concomitantly with adequate doses of penicillin.
Prophylaxis against recurrences of rheumatic fever, as an alternative to penicillin.
H. influenzae meningitis, as adjunctive therapy with parental streptomycin. Launch Date1994 |
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Sources: https://www.drugs.com/pro/sulfadiazine.html |
Curative | Sulfadiazine Approved UseSulfadiazine tablets USP are indicated in the following conditions:
Chancroid
Trachoma
Inclusion conjunctivitis
Nocardiosis
Urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) in the absence of obstructive uropathy or foreign bodies, when these infections are caused by susceptible strains of the following organisms: Escherichia coli, Klebsiella species, Enterobacter species, Staphylococcus aureus, Proteus mirabilis and P. vulgaris. Sulfadiazine should be used for urinary tract infections only after use of more soluble sulfonamides has been unsuccessful.
Toxoplasmosis encephalitis in patients with and without acquired immunodeficiency syndrome, as adjunctive therapy with pyrimethamine.
Malaria due to chloroquine-resistant strains of Plasmodium falciparum, when used as adjunctive therapy.
Prophylaxis of meningococcal meningitis when sulfonamide-sensitive group A strains are known to prevail in family groups or larger closed populations (the prophylactic usefulness of sulfonamides when group B or C infections are prevalent is not proved and may be harmful in closed population groups).
Meningococcal meningitis, when the organism has been demonstrated to be susceptible.
Acute otitis media due to Haemophilusinfluenzae, when used concomitantly with adequate doses of penicillin.
Prophylaxis against recurrences of rheumatic fever, as an alternative to penicillin.
H. influenzae meningitis, as adjunctive therapy with parental streptomycin. Launch Date1994 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
84.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14742225/ |
2 g 2 times / day steady-state, oral dose: 2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
SULFADIAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.247 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14742225/ |
2 g 2 times / day steady-state, oral dose: 2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
SULFADIAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14742225/ |
2 g 2 times / day steady-state, oral dose: 2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
SULFADIAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Disc. AE: Stenocardia, Distress gastrointestinal... Other AEs: Thrombopenia, Creatinine serum increased... AEs leading to discontinuation/dose reduction: Stenocardia (grade 3, 5%) Other AEs:Distress gastrointestinal (grade 3, 5%) Skin rash (grade 3, 5%) Thrombopenia (9%) Sources: Page: p.36, 38Creatinine serum increased (5%) Elevated liver enzyme levels (5%) Malaise (23%) Diarrhea (5%) |
1 g 4 times / day steady, oral Recommended Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.4 |
unhealthy, 29.81 n = 16 Health Status: unhealthy Condition: Cerebral toxoplasmosis Age Group: 29.81 Sex: M+F Population Size: 16 Sources: Page: p.4 |
Disc. AE: Stevens Johnson syndrome, Thrombocytopenia... Other AEs: Skin rash, Neutropenia... AEs leading to discontinuation/dose reduction: Stevens Johnson syndrome (grade 3, 1.16%) Other AEs:Thrombocytopenia (grade 4, 25%) Major bleed (grade 4, 25%) Skin rash (1.16%) Sources: Page: p.4Neutropenia (18.75%) Febrile neutropenia (1.16%) |
6 g 1 times / day steady, oral (max) Recommended Dose: 6 g, 1 times / day Route: oral Route: steady Dose: 6 g, 1 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.476 |
unhealthy, 33.8 n = 29 Health Status: unhealthy Condition: Central nervous system toxoplasmosis Age Group: 33.8 Sex: M+F Population Size: 29 Sources: Page: p.476 |
Disc. AE: Skin rash, Neutropenia... AEs leading to discontinuation/dose reduction: Skin rash (grade 3, 17.24%) Sources: Page: p.476Neutropenia (grade 3, 3.45%) Acute renal failure (grade 3, 6.9%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Malaise | 23% | 4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Creatinine serum increased | 5% | 4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Diarrhea | 5% | 4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Elevated liver enzyme levels | 5% | 4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Thrombopenia | 9% | 4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Distress gastrointestinal | grade 3, 5% Disc. AE |
4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Skin rash | grade 3, 5% Disc. AE |
4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Stenocardia | grade 3, 5% Disc. AE |
4 g 1 times / day steady, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Co-administed with:: pyrimethamine(50 mg oral; 1/day) Sources: Page: p.36, 38folinic acid(15 mg oral; 1/day) |
unhealthy, 16 - 80 n = 22 Health Status: unhealthy Condition: Ocular toxoplasmosis Age Group: 16 - 80 Sex: M+F Population Size: 22 Sources: Page: p.36, 38 |
Febrile neutropenia | 1.16% | 1 g 4 times / day steady, oral Recommended Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.4 |
unhealthy, 29.81 n = 16 Health Status: unhealthy Condition: Cerebral toxoplasmosis Age Group: 29.81 Sex: M+F Population Size: 16 Sources: Page: p.4 |
Skin rash | 1.16% | 1 g 4 times / day steady, oral Recommended Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.4 |
unhealthy, 29.81 n = 16 Health Status: unhealthy Condition: Cerebral toxoplasmosis Age Group: 29.81 Sex: M+F Population Size: 16 Sources: Page: p.4 |
Neutropenia | 18.75% | 1 g 4 times / day steady, oral Recommended Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.4 |
unhealthy, 29.81 n = 16 Health Status: unhealthy Condition: Cerebral toxoplasmosis Age Group: 29.81 Sex: M+F Population Size: 16 Sources: Page: p.4 |
Stevens Johnson syndrome | grade 3, 1.16% Disc. AE |
1 g 4 times / day steady, oral Recommended Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.4 |
unhealthy, 29.81 n = 16 Health Status: unhealthy Condition: Cerebral toxoplasmosis Age Group: 29.81 Sex: M+F Population Size: 16 Sources: Page: p.4 |
Major bleed | grade 4, 25% Disc. AE |
1 g 4 times / day steady, oral Recommended Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.4 |
unhealthy, 29.81 n = 16 Health Status: unhealthy Condition: Cerebral toxoplasmosis Age Group: 29.81 Sex: M+F Population Size: 16 Sources: Page: p.4 |
Thrombocytopenia | grade 4, 25% Disc. AE |
1 g 4 times / day steady, oral Recommended Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.4 |
unhealthy, 29.81 n = 16 Health Status: unhealthy Condition: Cerebral toxoplasmosis Age Group: 29.81 Sex: M+F Population Size: 16 Sources: Page: p.4 |
Skin rash | grade 3, 17.24% Disc. AE |
6 g 1 times / day steady, oral (max) Recommended Dose: 6 g, 1 times / day Route: oral Route: steady Dose: 6 g, 1 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.476 |
unhealthy, 33.8 n = 29 Health Status: unhealthy Condition: Central nervous system toxoplasmosis Age Group: 33.8 Sex: M+F Population Size: 29 Sources: Page: p.476 |
Neutropenia | grade 3, 3.45% Disc. AE |
6 g 1 times / day steady, oral (max) Recommended Dose: 6 g, 1 times / day Route: oral Route: steady Dose: 6 g, 1 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.476 |
unhealthy, 33.8 n = 29 Health Status: unhealthy Condition: Central nervous system toxoplasmosis Age Group: 33.8 Sex: M+F Population Size: 29 Sources: Page: p.476 |
Acute renal failure | grade 3, 6.9% Disc. AE |
6 g 1 times / day steady, oral (max) Recommended Dose: 6 g, 1 times / day Route: oral Route: steady Dose: 6 g, 1 times / day Co-administed with:: pyrimethamine(50-75 mg oral; 1/day) Sources: Page: p.476 |
unhealthy, 33.8 n = 29 Health Status: unhealthy Condition: Central nervous system toxoplasmosis Age Group: 33.8 Sex: M+F Population Size: 29 Sources: Page: p.476 |
PubMed
Title | Date | PubMed |
---|---|---|
Systematic review of the use of honey as a wound dressing. | 2001 |
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Depletion study of trimethoprim and sulphadiazine in milk and its relationship with mastitis pathogenic bacteria strains minimum inhibitory concentrations (MICs) in dairy cows. | 2001 Apr |
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In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents. | 2001 Feb 26 |
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Preparation of collagen modified hyaluronan microparticles as antibiotics carrier. | 2001 Jun |
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Wound healing activity of the aqueous extract of Thespesia populnea fruit. | 2001 Jun |
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Characterization of class 1 integrons associated with R-plasmids in clinical Aeromonas salmonicida isolates from various geographical areas. | 2001 Jun |
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Exposure to liquid sulfur mustard. | 2001 Jun |
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Resolution of microsporidial keratoconjunctivitis in an AIDS patient treated with highly active antiretroviral therapy. | 2001 Mar |
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Pitfalls in imaging Hodgkin's disease with computed tomography and positron emission tomography using fluorine-18-fluorodeoxyglucose. | 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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Clinical microbiological case: visual problems in an HIV-positive patient. | 2001 Nov |
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Myelitis and ascending flaccid paralysis due to congenital toxoplasmosis. | 2001 Nov 15 |
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Crystalluria with sulphadiazine. | 2001 Oct |
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Suspected protozoal myeloencephalitis in a two-month-old colt. | 2001 Sep 1 |
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Transfer and distribution profiles of dietary sulphonamides in the tissues of the laying hen. | 2002 Apr |
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Outbreak of serogroup W135 meningococcal disease after the Hajj pilgrimage, Europe, 2000. | 2002 Aug |
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Effect of sulphadiazine and trimethoprim on the immune response of rainbow trout (Oncorhynchus mykiss). | 2002 Feb |
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Complete osseous regeneration of a large skull defect in a patient with cutis aplasia: a conservative approach. | 2002 Jul |
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An update on current practices in the management of ocular toxoplasmosis. | 2002 Jul |
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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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[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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/sulfadiazine.html
Curator's Comment: Can also be used topically http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Set_Current_Drug&ApplNo=018810&DrugName=THERMAZENE&ActiveIngred=SILVER%20SULFADIAZINE&SponsorApplicant=THEPHARMANETWORK%20LLC&ProductMktStatus=1&goto=Search.DrugDetails
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20182664
Sulfadiazine inhibited Pseudomonas aeruginosa with MIC 256 ug/mL
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C29739
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SUB10696MIG
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CHEMBL439
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547-32-0
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C66566
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117870
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ACTIVE MOIETY
SUBSTANCE RECORD