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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomySulfadiazine
Identification
- Name
- Sulfadiazine
- Accession Number
- DB00359 (APRD00190)
- Type
- Small Molecule
- Groups
- Approved, Investigational, 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
Structure for Sulfadiazine (DB00359)
- 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
- Product Ingredients
Ingredient UNII CAS InChI Key Sulfadiazine sodium 84CS1P306F 547-32-0 JLDCNMJPBBKAHH-UHFFFAOYSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Sulfadiazine Tab 7.7gr Tablet 500.5 mg Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1957-12-31 2001-07-20 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Sulfadiazine Tablet 500 mg/1 Oral Remedy Repack 2012-09-20 2013-03-25 US 
Sulfadiazine Tablet 500 mg/1 Oral Eon Labs, Inc. 1994-07-29 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Coptin Oral Suspension Sulfadiazine (41 mg) + Trimethoprim (9 mg) Suspension Oral Axcan Pharma 1979-12-31 2006-09-12 Canada Coptin Tab Sulfadiazine (410 mg) + Trimethoprim (90 mg) Tablet Oral Pfizer 1979-12-31 1996-09-09 Canada Coptin Tab Sulfadiazine (410 mg) + Trimethoprim (90 mg) Tablet Oral Axcan Pharma 1979-12-31 2006-09-12 Canada Ovoquinol Cones Sulfadiazine (400 mg) + Diiodohydroxyquinoline (75 mg) + Undecylenic acid (50 mg) Suppository Vaginal Lab Nadeau LtÉe, Division Of Technilab Inc. 1963-12-31 1999-09-28 Canada Ovoquinol Crm Vaginale Sulfadiazine (8 %) + Diiodohydroxyquinoline (2 %) + Undecylenic acid (1 %) Cream Vaginal Lab Nadeau LtÉe, Division Of Technilab Inc. 1980-12-31 1999-09-28 Canada Trisulfaminic Sus Sulfadiazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfamerazine (167 mg) + Sulfamethazine (167 mg) Suspension Oral Shepherd Pharmaceuticals Inc. 1959-12-31 2001-04-11 Canada Trisulfaminic Tab Sulfadiazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfamerazine (167 mg) + Sulfamethazine (167 mg) Tablet Oral Shepherd Pharmaceuticals Inc. 1959-12-31 2001-04-11 Canada - International/Other Brands
- Adiazine
- Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Antiparasitic Agents
- Antiprotozoals
- Blood Glucose Lowering Agents
- Coccidiostats
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Hypoglycemia-Associated Agents
- Intermediate-Acting Sulfonamides
- Methemoglobinemia Associated Agents
- Sulfanilamides
- Sulfonamide Antibacterial
- Sulfonamides
- Sulfones
- Sulfur Compounds
- UNII
- 0N7609K889
- CAS number
- 68-35-9
- Weight
- Average: 250.277
Monoisotopic: 250.052446274 - Chemical Formula
- C10H10N4O2S
- 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
Pharmacology
- Indication
For the treatment of rheumatic fever and meningococcal meningitis
- Associated Conditions
- Chancroid
- Chlamydial Infections
- Conjunctivitis, Inclusion
- Meningitis caused by Haemophilus influenzae
- Meningococcal Meningitis
- Nocardiosis
- Plague
- Plasmodium Infections
- Toxoplasmosis
- Trachoma
- Urinary Tract Infections (UTIs)
- Wound Sepsis
- Bacterial otitis media caused by Haemophilus influenzae
- Prophylaxis of Rheumatic fever
- Recurrent Rheumatic fever
- 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.
Target Actions Organism ADihydropteroate synthetase inhibitorPlasmodium 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
- Toxicity
Oral LD50 in mouse is 1500 mg/kg.
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The risk or severity of bleeding can be increased when Sulfadiazine is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Sulfadiazine is combined with (S)-Warfarin. 2,4-thiazolidinedione The therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Sulfadiazine. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Sulfadiazine. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Sulfadiazine. 5-(2-methylpiperazine-1-sulfonyl)isoquinoline The therapeutic efficacy of Sulfadiazine can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline. 5-androstenedione The metabolism of 5-androstenedione can be decreased when combined with Sulfadiazine. 6-Deoxyerythronolide B The metabolism of Sulfadiazine can be decreased when combined with 6-Deoxyerythronolide B. 6-O-benzylguanine The metabolism of 6-O-benzylguanine can be decreased when combined with Sulfadiazine. 9-aminocamptothecin The metabolism of 9-aminocamptothecin can be decreased when combined with Sulfadiazine. - Food Interactions
- Not 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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014503
- KEGG Drug
- D00587
- KEGG Compound
- C07658
- PubChem Compound
- 5215
- PubChem Substance
- 46506164
- ChemSpider
- 5026
- BindingDB
- 50166571
- ChEBI
- 9328
- ChEMBL
- CHEMBL439
- Therapeutic Targets Database
- DAP001238
- PharmGKB
- PA451539
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sulfadiazine
- ATC Codes
- J01EE06 — Sulfadiazine and tetroxoprim
- J01EE — Combinations of sulfonamides and trimethoprim, incl. derivatives
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- J01EC — Intermediate-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- MSDS
- Download (73.5 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Recruiting Treatment Osteomyelitis 1 2 Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Toxoplasmosis, Cerebral 1 2 Completed Treatment Minor burns 1 3 Completed Treatment Toxoplasmosis, Congenital 1 4 Recruiting Treatment Toxoplasmosis 1
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
Form Route Strength Suspension Oral Tablet Oral Suppository Vaginal Cream Vaginal Tablet Oral 500 mg/1 Tablet Oral 500.5 mg - Prices
Unit description Cost Unit Silver Sulfadiazine 1% Cream 400 gm Jar 36.48USD jar Silver Sulfadiazine 1% Cream 50 gm Jar 21.99USD jar Silver Sulfadiazine 1% Cream 85 gm Jar 19.99USD jar Silver Sulfadiazine 1% Cream 25 gm Jar 13.99USD jar Sulfadiazine 500 mg tablet 2.5USD tablet Sulfazine EC 500 mg Enteric Coated Tabs 0.42USD tab Sulfazine ec 500 mg tablet 0.38USD tablet Sulfazine 500 mg tablet 0.25USD tablet Sulfadiazine powder 0.13USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 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 0.601 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 64.2 m3·mol-1 ChemAxon Polarizability 24.39 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9877 Blood Brain Barrier + 0.9383 Caco-2 permeable + 0.6988 P-glycoprotein substrate Non-substrate 0.9012 P-glycoprotein inhibitor I Non-inhibitor 0.913 P-glycoprotein inhibitor II Non-inhibitor 0.9156 Renal organic cation transporter Non-inhibitor 0.8437 CYP450 2C9 substrate Non-substrate 0.8031 CYP450 2D6 substrate Non-substrate 0.915 CYP450 3A4 substrate Non-substrate 0.7671 CYP450 1A2 substrate Non-inhibitor 0.9574 CYP450 2C9 inhibitor Non-inhibitor 0.922 CYP450 2D6 inhibitor Non-inhibitor 0.9548 CYP450 2C19 inhibitor Non-inhibitor 0.9693 CYP450 3A4 inhibitor Non-inhibitor 0.902 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8569 Ames test Non AMES toxic 0.9206 Carcinogenicity Non-carcinogens 0.9393 Biodegradation Not ready biodegradable 0.9973 Rat acute toxicity 1.8353 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9383 hERG inhibition (predictor II) Non-inhibitor 0.8673
Spectra
- Mass Spec (NIST)
- Download (7.99 KB)
- Spectra
Taxonomy
- 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
- Aminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Pyrimidine / Organosulfonic acid amide / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Heteroaromatic compound / Aminosulfonyl compound / Sulfonyl show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- substituted aniline, sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:9328)
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
- Uniprot Name
- Dihydropteroate synthetase
- Molecular Weight
- 43370.845 Da
References
- 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]
- 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]
- 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
- 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
- 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. [PubMed:10725317]
- 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]
- A Review on Drug Interactions in Oral Hypoglycemic Drugs by Mechanism of Cytochrome P450 Enzyme Inhibition [File]
- 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 un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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]
- 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. [PubMed:26721703]
- 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 ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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]
Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 08:51