Banner
targets (1) enzymes (4)
for drugs
Identification
Name Sulfadiazine
Accession Number DB00359 (APRD00190)
Type small molecule
Groups approved
Description

One of the short-acting sulfonamides used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
SDA
Sulfadiazene
Sulfadiazin
Sulfanilamidopyrimidine
Sulfapirimidin
Sulfapyrimidin
Sulfapyrimidine
Sulphadiazine
Salts Not Available
Brand names
Name Company
Adiazin
Adiazine
Coco-Diazine
Cocodiazine
Codiazine
Cremodiazine
Cremotres
Debenal
Deltazina
Diazin
Diazolone
Diazovit
Diazyl
Eskadiazine
Honey Diazine
Lantrisul
Lipo-Diazine
Lipo-Levazine
Liquadiazine
Metha-Meridiazine
Microsulfon
Neazine
Neotrizine
Palatrize
Pecta-Diazine
Piridisir
Pirimal
Pyrimal
Quadetts
Quadramoid
Sanodiazine
Spofadrizine
Sterazine
Sulfa-Triple #2
Sulfacombin
Sulfaloid
Sulfatryl
Sulfazine
Sulfolex
Sulfonamides Duplex
Sulfonsol
Sulfose
Terfonyl
Theradiazine
Tri-Sulfameth
Trifonamide
Triple Sulfas
Triple Sulfoid
Trisem
Truozine
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anti-Infective Agents
  • Anti-Infectives
  • Antiprotozoals
  • Antiprotozoal Agents
  • Coccidiostats
CAS number 68-35-9
Weight Average: 250.277
Monoisotopic: 250.052446274
Chemical Formula C10H10N4O2S
InChI Key InChIKey=SEEPANYCNGTZFQ-UHFFFAOYSA-N
InChI
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)
Plain Text
IUPAC Name
4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1
Plain Text
Mass Spec show (7.99 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzenesulfonamides
  • Sulfanilamides
Substructures
  • Sulfonyls
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Benzenesulfonamides
  • Pyrimidines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Sulfanilamides
  • Sulfonamides
  • Cyanamides
  • Anilines
Pharmacology
Indication For the treatment of rheumatic fever and meningococcal meningitis
Pharmacodynamics 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.
Mechanism of action 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Sulfadiazine is excreted largely in the urine.
Half life Not Available
Clearance Not Available
Toxicity Oral LD50 in mouse is 1500 mg/kg.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
  • Everylife
  • Impax laboratories inc
  • Lannett co inc
  • Lederle laboratories div american cyanamid co
  • Eli lilly and co
  • Sandoz inc
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Silver Sulfadiazine 1% Cream 400 gm Jar 36.48 USD jar
Silver Sulfadiazine 1% Cream 50 gm Jar 21.99 USD jar
Silver Sulfadiazine 1% Cream 85 gm Jar 19.99 USD jar
Silver Sulfadiazine 1% Cream 25 gm Jar 13.99 USD jar
Sulfadiazine 500 mg tablet 2.5 USD tablet
Sulfazine EC 500 mg Enteric Coated Tabs 0.42 USD tab
Sulfazine ec 500 mg tablet 0.38 USD tablet
Sulfazine 500 mg tablet 0.25 USD tablet
Sulfadiazine powder 0.13 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 255.5 dec °C PhysProp
water solubility 77 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -0.09 HANSCH,C ET AL. (1995)
logS -3.51 ADME Research, USCD
pKa 6.36 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 6.01e-01 g/l ALOGPS
logP 0.25 ALOGPS
logP 0.39 ChemAxon
logS -2.6 ALOGPS
pKa (strongest acidic) 6.99 ChemAxon
pKa (strongest basic) 2.01 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 97.97 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 64.2 ChemAxon
polarizability 24.39 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00587 Link_out
KEGG Compound C07658 Link_out
PubChem Compound 5215 Link_out
PubChem Substance 46506164 Link_out
ChemSpider 5026 Link_out
ChEBI 9328 Link_out
ChEMBL 9328 Link_out
Therapeutic Targets Database DAP001238 Link_out
PharmGKB PA451539 Link_out
Drugs.com http://www.drugs.com/cdi/sulfadiazine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Sulfadiazine Link_out
ATC Codes
  • D06BA01
  • J01EC02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (73.5 KB)
Interactions
Drug Interactions
Drug Interaction
Chlorpropamide Sulfonamide/sulfonylurea: possible hypoglycemia
Cyclosporine The sulfonamide decreases the effect of cyclosporine
Fosphenytoin The sulfonamide increases the effect of hydantoin
Methenamine mandelate Possible crystallization of urates with this combination
Methotrexate The sulfamide increases the toxicity of methotrexate
Phenytoin The sulfonamide increases the effect of hydantoin
Tamoxifen Sulfadiazine may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfadiazine is initiated, discontinued or dose changed.
Tolbutamide Tolbutamide and Sulfadiazine are strong CYP2C9 inhibitors and substrates. Decreased metabolism and clearance of both agents may occur during concomitant therapy. Consider alternate therpy or monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose(s) changed.
Torasemide Sulfadiazine, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Sulfadiazine is initiated, discontinued or dose changed.
Trimethoprim The strong CYP2C9 inhibitor, Sulfadiazine, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Sulfadiazine is initiated, discontinued or dose changed.
Warfarin Sulfadiazine, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if sulfadiazine is initiated, discontinued or dose changed.
Zafirlukast Sulfadiazine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if sulfadiazine is initiated, discontinued or dose changed.
Food Interactions Not Available
Targets

1. Dihydropteroate synthetase

Pharmacological action: yes
Actions: inhibitor
Organism class: parasitic
UniProt ID: Q27738 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA

References:
  1. de Araujo MV, Vieira EK, Silva Lazaro G, Conegero LS, Almeida LE, Barreto LS, da Costa NB Jr, Gimenez IF: Sulfadiazine/hydroxypropyl-beta-cyclodextrin host-guest system: Characterization, phase-solubility and molecular modeling. Bioorg Med Chem. 2008 May 15;16(10):5788-94. Epub 2008 Mar 27. Pubmed
  2. Iliades P, Meshnick SR, Macreadie IG: Mutations in the Pneumocystis jirovecii DHPS gene confer cross-resistance to sulfa drugs. Antimicrob Agents Chemother. 2005 Feb;49(2):741-8. Pubmed
  3. Prabhu V, Lui H, King J: Arabidopsis dihydropteroate synthase: general properties and inhibition by reaction product and sulfonamides. Phytochemistry. 1997 May;45(1):23-7. Pubmed
Enzymes

1. Cytochrome P450 2C9

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C8

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

UniProt ID: P10632 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2E1

Actions: substrate

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 3A4

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19