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Identification
NameSulfadiazine
Accession NumberDB00359  (APRD00190)
TypeSmall Molecule
GroupsApproved, Vet 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
Synonyms
2-sulfanilamidopyrimidine
2-sulfanilylaminopyrimidine
4-amino-N-2-pyrimidinylbenzenesulfonamide
N(1)-2-Pyrimidinylsulfanilamide
N(1)-2-Pyrimidylsulfanilamide
N1-2-pyrimidinylsulfanilamide
N1-2-pyrimidylsulfanilamide
Sulfadiazina
Sulfadiazine
Sulfadiazinum
Sulfapyrimidine
Sulphadiazine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sulfadiazine Tab 7.7grtablet500.5 mgoralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312001-07-20Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sulfadiazinetablet500 mg/1oralEon Labs, Inc.1994-07-29Not applicableUs
Sulfadiazinetablet500 mg/1oralREMEDYREPACK INC.2013-02-11Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdiazineNot Available
Brand mixtures
NameLabellerIngredients
Coptin Oral SuspensionAxcan Pharma Inc
Coptin TabPfizer Canada Inc
Trisulfaminic SusShepherd Pharmaceuticals Inc.
Trisulfaminic TabShepherd Pharmaceuticals Inc.
Salts
Name/CASStructureProperties
Sulfadiazine sodium
ThumbNot applicableDBSALT001400
Categories
UNII0N7609K889
CAS number68-35-9
WeightAverage: 250.277
Monoisotopic: 250.052446274
Chemical FormulaC10H10N4O2S
InChI KeyInChIKey=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)
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 inhibitorNon-inhibitor0.922
CYP450 2D6 inhibitorNon-inhibitor0.9548
CYP450 2C19 inhibitorNon-inhibitor0.9693
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Suspensionoral
Tabletoral
Tabletoral500 mg/1
Tabletoral500.5 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)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 ReferencesNot Available
External Links
ATC CodesJ01EE06J01EE02J01EC02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.5 KB)
Interactions
Drug Interactions
Drug
AcetohexamideAcetohexamide may increase the hypoglycemic activities of Sulfadiazine.
Acetylsalicylic acidAcetylsalicylic acid may increase the hypoglycemic activities of Sulfadiazine.
AlogliptinAlogliptin may increase the hypoglycemic activities of Sulfadiazine.
BosentanThe serum concentration of Bosentan can be increased when it is combined with Sulfadiazine.
CanagliflozinCanagliflozin may increase the hypoglycemic activities of Sulfadiazine.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Sulfadiazine.
CeritinibThe serum concentration of Sulfadiazine can be increased when it is combined with Ceritinib.
ChlorpropamideSulfadiazine may increase the hypoglycemic activities of Chlorpropamide.
CyclosporineSulfadiazine may increase the nephrotoxic activities of Cyclosporine.
DabrafenibThe serum concentration of Sulfadiazine can be decreased when it is combined with Dabrafenib.
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Sulfadiazine.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfadiazine.
DiclofenacThe serum concentration of Diclofenac can be increased when it is combined with Sulfadiazine.
DicoumarolSulfadiazine may increase the anticoagulant activities of Dicoumarol.
DihydrotestosteroneDihydrotestosterone may increase the hypoglycemic activities of Sulfadiazine.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Sulfadiazine.
FloxuridineThe metabolism of Sulfadiazine can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Sulfadiazine can be decreased when combined with Fluconazole.
GliclazideGliclazide may increase the hypoglycemic activities of Sulfadiazine.
GlimepirideGlimepiride may increase the hypoglycemic activities of Sulfadiazine.
GliquidoneGliquidone may increase the hypoglycemic activities of Sulfadiazine.
GlyburideGlyburide may increase the hypoglycemic activities of Sulfadiazine.
HexamethylenetetramineThe risk or severity of adverse effects can be increased when Hexamethylenetetramine is combined with Sulfadiazine.
Insulin AspartInsulin Aspart may increase the hypoglycemic activities of Sulfadiazine.
Insulin DetemirInsulin Detemir may increase the hypoglycemic activities of Sulfadiazine.
Insulin GlargineInsulin Glargine may increase the hypoglycemic activities of Sulfadiazine.
Insulin GlulisineInsulin Glulisine may increase the hypoglycemic activities of Sulfadiazine.
Insulin HumanInsulin Regular may increase the hypoglycemic activities of Sulfadiazine.
Insulin LisproInsulin Lispro may increase the hypoglycemic activities of Sulfadiazine.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Sulfadiazine.
LinagliptinLinagliptin may increase the hypoglycemic activities of Sulfadiazine.
LumacaftorThe serum concentration of Sulfadiazine can be decreased when it is combined with Lumacaftor.
MecamylamineThe risk or severity of adverse effects can be increased when Sulfadiazine is combined with Mecamylamine.
MetforminMetformin may increase the hypoglycemic activities of Sulfadiazine.
MethotrexateThe risk or severity of adverse effects can be increased when Sulfadiazine is combined with Methotrexate.
MifepristoneThe serum concentration of Sulfadiazine can be increased when it is combined with Mifepristone.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Sulfadiazine.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Sulfadiazine.
OxandroloneOxandrolone may increase the hypoglycemic activities of Sulfadiazine.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Sulfadiazine.
ParoxetineParoxetine may increase the hypoglycemic activities of Sulfadiazine.
PegvisomantPegvisomant may increase the hypoglycemic activities of Sulfadiazine.
PhenelzinePhenelzine may increase the hypoglycemic activities of Sulfadiazine.
PhenytoinThe metabolism of Sulfadiazine can be increased when combined with Phenytoin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Sulfadiazine.
PorfimerSulfadiazine may increase the photosensitizing activities of Porfimer.
PrilocaineThe risk or severity of adverse effects can be increased when Sulfadiazine is combined with Prilocaine.
ProcaineThe therapeutic efficacy of Sulfadiazine can be decreased when used in combination with Procaine.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Sulfadiazine.
RepaglinideRepaglinide may increase the hypoglycemic activities of Sulfadiazine.
SaxagliptinSaxagliptin may increase the hypoglycemic activities of Sulfadiazine.
SecobarbitalThe metabolism of Sulfadiazine can be increased when combined with Secobarbital.
SildenafilThe metabolism of Sildenafil can be decreased when combined with Sulfadiazine.
Sodium NitriteThe risk or severity of adverse effects can be increased when Sulfadiazine is combined with Sodium Nitrite.
SparfloxacinSparfloxacin may increase the hypoglycemic activities of Sulfadiazine.
SulfisoxazoleThe metabolism of Sulfadiazine can be decreased when combined with Sulfisoxazole.
TestosteroneTestosterone may increase the hypoglycemic activities of Sulfadiazine.
TolbutamideTolbutamide may increase the hypoglycemic activities of Sulfadiazine.
TranylcypromineTranylcypromine may increase the hypoglycemic activities of Sulfadiazine.
VerteporfinSulfadiazine may increase the photosensitizing activities of Verteporfin.
VildagliptinVildagliptin may increase the hypoglycemic activities of Sulfadiazine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
yes
Actions
inhibitor
General Function:
Dihydropteroate synthase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q27738
Molecular Weight:
43370.845 Da
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. doi: 10.1016/j.bmc.2008.03.057. Epub 2008 Mar 27. [PubMed:18434167 ]
  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:15673759 ]
  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:9127492 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
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, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
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...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
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.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23