Sulfadiazine

Identification

Summary

Sulfadiazine is a sulfonamide antibiotic used in a variety of infections, such as urinary tract infections, trachoma, and chancroid.

Generic Name
Sulfadiazine
DrugBank Accession Number
DB00359
Background

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.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 250.277
Monoisotopic: 250.052446274
Chemical Formula
C10H10N4O2S
Synonyms
  • 2-sulfanilamidopyrimidine
  • 2-sulfanilylaminopyrimidine
  • 4-amino-N-2-pyrimidinylbenzenesulfonamide
  • N(1)-2-Pyrimidinylsulfanilamide
  • N(1)-2-Pyrimidylsulfanilamide
  • Sulfadiazin
  • Sulfadiazina
  • Sulfadiazine
  • Sulfadiazinum
  • Sulfapyrimidine
  • Sulphadiazine

Pharmacology

Indication

For the treatment of rheumatic fever and meningococcal meningitis

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in treatment ofAcute otitis media caused by haemophilus influenzae••••••••••••
Treatment ofChancroid••••••••••••
Adjunct therapy in treatment ofEncephalitis•••••••••••••••••••• •••••• •••••••••• •••••••• ••••••
Treatment ofInclusion conjunctivitis••••••••••••
Adjunct therapy in treatment ofMalaria caused by plasmodium falciparum••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ADihydropteroate synthetase
inhibitor
Plasmodium falciparum
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

Adverse Effects
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Toxicity

Oral LD50 in mouse is 1500 mg/kg.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirSulfadiazine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Sulfadiazine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Sulfadiazine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Sulfadiazine can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Sulfadiazine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sulfadiazine sodium84CS1P306F547-32-0JLDCNMJPBBKAHH-UHFFFAOYSA-N
International/Other Brands
Adiazine
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Sulfadiazine Tab 7.7grTablet500.5 mg / tabOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312001-07-20Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SulfadiazineTablet500 mg/1OralRemedy Repack2012-09-202013-03-25US flag
SulfadiazineTablet500 mg/1OralEpic Pharma, LLC2021-12-15Not applicableUS flag
SulfadiazineTablet500 mg/1OralEon Labs, Inc.1994-07-292024-05-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Coptin Oral SuspensionSulfadiazine (41 mg / mL) + Trimethoprim (9 mg / mL)SuspensionOralAxcan Pharma1979-12-312006-09-12Canada flag
Coptin TabSulfadiazine (410 mg / tab) + Trimethoprim (90 mg / tab)TabletOralPfizer Canada Ulc1979-12-311996-09-09Canada flag
Coptin TabSulfadiazine (410 mg) + Trimethoprim (90 mg)TabletOralAxcan Pharma1979-12-312006-09-12Canada flag
Ovoquinol ConesSulfadiazine (400 mg / sup) + Diiodohydroxyquinoline (75 mg / sup) + Undecylenic acid (50 mg / sup)SuppositoryVaginalLab Nadeau LtÉe, Division Of Technilab Inc.1963-12-311999-09-28Canada flag
Ovoquinol Crm VaginaleSulfadiazine (8 %) + Diiodohydroxyquinoline (2 %) + Undecylenic acid (1 %)CreamVaginalLab Nadeau LtÉe, Division Of Technilab Inc.1980-12-311999-09-28Canada flag

Categories

ATC Codes
J01EE06 — Sulfadiazine and tetroxoprimJ01EC02 — SulfadiazineG01AE10 — Combinations of sulfonamidesJ01EE02 — Sulfadiazine and trimethoprim
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Aminobenzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / Pyrimidines and pyrimidine derivatives / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
substituted aniline, sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:9328)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
0N7609K889
CAS number
68-35-9
InChI Key
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

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 References
Not Available
Human Metabolome Database
HMDB0014503
KEGG Drug
D00587
KEGG Compound
C07658
PubChem Compound
5215
PubChem Substance
46506164
ChemSpider
5026
BindingDB
50166571
RxNav
10171
ChEBI
9328
ChEMBL
CHEMBL439
ZINC
ZINC000000120319
Therapeutic Targets Database
DAP001238
PharmGKB
PA451539
Drugs.com
Drugs.com Drug Page
Wikipedia
Sulfadiazine
MSDS
Download (73.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionBurns1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Toxoplasmic Encephalitis1
4RecruitingTreatmentToxoplasmosis1
3CompletedTreatmentToxoplasmosis, Congenital1
3Unknown StatusTreatmentChorioretinitis1

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
  • Amend
  • A-S Medication Solutions LLC
  • C.O. Truxton Inc.
  • Eon Labs
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • Qualitest
Dosage Forms
FormRouteStrength
SuspensionOral5 g
SuppositoryVaginal
CreamVaginal
Powder, for solutionOral
PowderNot applicable1 g/1g
TabletOral
TabletOral500 mg/1
TabletOral500.5 mg / tab
SolutionOral
TabletOral500 mg
Injection, solutionIntramuscular; Intravenous
SuspensionOral
TabletOral
SuspensionOral325 mg/5ml
TabletOral250 mg
Suspension
PowderTopical
Tablet
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)255.5 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
Polarizability24.34 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Download (7.99 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0f8a-9340000000-39ac1159346610a1332b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0090000000-1bc83eabade65dc8953a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0910000000-bd163c77861c5a8afa49
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-260a572b5c7f3c070c26
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052r-0900000000-580f983ba25c4cb3eb30
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1900000000-8dc8c152ec6044f1c2e9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0090000000-23afa7ea3ef67a93a2e6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pb9-3960000000-355dcad6c59ae9c75fb7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-4900000000-337c5e4fc08cc648b85d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-8900000000-63cd0dba3c4894d64ae1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-9500000000-64c8a8332030e3f700a1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05mo-9300000000-746250effd08ec8bf51b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0090000000-e8005ac37727f1c540d8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pb9-2960000000-ff127258fb7c09ae3665
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-4900000000-4fa5b350b17254bc9a1a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-8900000000-4a998ad7772889643c1f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-9500000000-7e0d8190b4e7f7ced956
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05mo-9300000000-9cca42d677a6ef782a2c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1900000000-4b5c2f7e29a6399f475c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0190000000-59e9b58116d6bb7c51e2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-49d816c2f0db18aa414a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0930000000-5dba725fc8e15c40340e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0960000000-7fd01c58027fe21e86d8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9000000000-01c4b42658058bf9b2fa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9200000000-aa1f9e595f71236a85b1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-165.688071
predicted
DarkChem Lite v0.1.0
[M-H]-165.366671
predicted
DarkChem Lite v0.1.0
[M-H]-153.52098
predicted
DeepCCS 1.0 (2019)
[M+H]+166.579971
predicted
DarkChem Lite v0.1.0
[M+H]+166.563871
predicted
DarkChem Lite v0.1.0
[M+H]+155.87901
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.853971
predicted
DarkChem Lite v0.1.0
[M+Na]+161.97215
predicted
DeepCCS 1.0 (2019)

Targets

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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
Uniprot Name
Dihydropteroate synthetase
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Winter HR, Unadkat JD: Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism. Drug Metab Dispos. 2005 Jul;33(7):969-76. doi: 10.1124/dmd.104.002998. Epub 2005 Apr 20. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data based on the findings of in vitro studies.
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Komatsu K, Ito K, Nakajima Y, Kanamitsu Si, Imaoka S, Funae Y, Green CE, Tyson CA, Shimada N, Sugiyama Y: Prediction of in vivo drug-drug interactions between tolbutamide and various sulfonamides in humans based on in vitro experiments. Drug Metab Dispos. 2000 Apr;28(4):475-81. [Article]
  2. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L58). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  3. A Review on Drug Interactions in Oral Hypoglycemic Drugs by Mechanism of Cytochrome P450 Enzyme Inhibition [File]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:24