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Identification
NameSulfadiazine
Accession NumberDB00359  (APRD00190)
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
2-sulfanilamidopyrimidineNot AvailableNot Available
2-sulfanilylaminopyrimidineNot AvailableNot Available
4-amino-N-2-pyrimidinylbenzenesulfonamideNot AvailableNot Available
N(1)-2-PyrimidinylsulfanilamideNot AvailableNot Available
N(1)-2-PyrimidylsulfanilamideNot AvailableNot Available
N1-2-pyrimidinylsulfanilamideNot AvailableNot Available
N1-2-pyrimidylsulfanilamideNot AvailableNot Available
SulfadiazinaNot AvailableNot Available
SulfadiazineNot AvailableNot Available
SulfadiazinumNot AvailableNot Available
SulfapyrimidineNot AvailableNot Available
SulphadiazineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sulfadiazinetablet500 mgoralEon Labs, Inc.1994-07-29Not AvailableUs
Sulfadiazinetablet500 mgoralREMEDYREPACK INC.2013-02-11Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
AdiazineNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number68-35-9
WeightAverage: 250.277
Monoisotopic: 250.052446274
Chemical FormulaC10H10N4O2S
InChI KeySEEPANYCNGTZFQ-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)
IUPAC Name
4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Sulfonylaniline
  • Substituted aniline
  • Aniline
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of rheumatic fever and meningococcal meningitis
PharmacodynamicsSulfadiazine 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 actionSulfadiazine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationSulfadiazine is excreted largely in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityOral LD50 in mouse is 1500 mg/kg.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9877
Blood Brain Barrier+0.9383
Caco-2 permeable+0.6988
P-glycoprotein substrateNon-substrate0.9012
P-glycoprotein inhibitor INon-inhibitor0.913
P-glycoprotein inhibitor IINon-inhibitor0.9156
Renal organic cation transporterNon-inhibitor0.8437
CYP450 2C9 substrateNon-substrate0.8031
CYP450 2D6 substrateNon-substrate0.915
CYP450 3A4 substrateNon-substrate0.7671
CYP450 1A2 substrateNon-inhibitor0.9574
CYP450 2C9 substrateNon-inhibitor0.922
CYP450 2D6 substrateNon-inhibitor0.9548
CYP450 2C19 substrateNon-inhibitor0.9693
CYP450 3A4 substrateNon-inhibitor0.902
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8569
Ames testNon AMES toxic0.9206
CarcinogenicityNon-carcinogens0.9393
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity1.8353 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9383
hERG inhibition (predictor II)Non-inhibitor0.8673
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
FormRouteStrength
Tabletoral500 mg
Prices
Unit descriptionCostUnit
Silver Sulfadiazine 1% Cream 400 gm Jar36.48USD jar
Silver Sulfadiazine 1% Cream 50 gm Jar21.99USD jar
Silver Sulfadiazine 1% Cream 85 gm Jar19.99USD jar
Silver Sulfadiazine 1% Cream 25 gm Jar13.99USD jar
Sulfadiazine 500 mg tablet2.5USD tablet
Sulfazine EC 500 mg Enteric Coated Tabs0.42USD tab
Sulfazine ec 500 mg tablet0.38USD tablet
Sulfazine 500 mg tablet0.25USD tablet
Sulfadiazine powder0.13USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point255.5 dec °CPhysProp
water solubility77 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.09HANSCH,C ET AL. (1995)
logS-3.51ADME Research, USCD
pKa6.36SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.601 mg/mLALOGPS
logP0.25ALOGPS
logP0.39ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)2.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.2 m3·mol-1ChemAxon
Polarizability24.39 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.99 KB)
SpectraNot Available
References
Synthesis Reference

Charles L. Fox, Jr., Shanta M. Modak, Paul Fox, “Wound dressing comprising silver sulfadiazine incorporated in animal tissue and method of preparation.” U.S. Patent US4599226, issued September, 1977.

US4599226
General ReferenceNot Available
External Links
ATC CodesJ01EC02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.5 KB)
Interactions
Drug Interactions
Drug
ChlorpropamideSulfonamide/sulfonylurea: possible hypoglycemia
CyclosporineThe sulfonamide decreases the effect of cyclosporine
FosphenytoinThe sulfonamide increases the effect of hydantoin
Methenamine mandelatePossible crystallization of urates with this combination
MethotrexateThe sulfamide increases the toxicity of methotrexate
PhenytoinThe sulfonamide increases the effect of hydantoin
TamoxifenSulfadiazine may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfadiazine is initiated, discontinued or dose changed.
TolbutamideTolbutamide 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.
TorasemideSulfadiazine, 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.
TrimethoprimThe 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.
WarfarinSulfadiazine, 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.
ZafirlukastSulfadiazine, 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 InteractionsNot Available

Targets

1. Dihydropteroate synthetase

Kind: protein

Organism: Plasmodium falciparum

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Dihydropteroate synthetase Q27738 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10