Sulfamethazine
Identification
- Name
- Sulfamethazine
- Accession Number
- DB01582
- Description
A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Sulfamethazine (DB01582)
- Weight
- Average: 278.33
Monoisotopic: 278.083746402 - Chemical Formula
- C12H14N4O2S
- Synonyms
- (p-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin
- 2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine
- 2-(p-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine
- 2-Sulfanilamido-4,6-dimethylpyrimidine
- 4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide
- 4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide
- 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
- 4,6-Dimethyl-2-sulfanilamidopyrimidine
- 6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin
- N-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide
- N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide
- N(1)-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide
- SMZ
- Sulfadimethyldiazine
- Sulfadimethylpyrimidine
- Sulfadimidina
- Sulfadimidine
- Sulfadimidinum
- Sulfametazina
- Sulfametazyny
- Sulfamethazine
- Sulfamezathine
- Sulphadimethylpyrimidine
- Sulphamethazine
- External IDs
- BN-2409
- NSC-67457
- NSC-683529
Pharmacology
- Indication
For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Sulfamethazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamethazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.
- Mechanism of action
Sulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.
Target Actions Organism ADihydropteroate synthase inhibitorEscherichia coli (strain K12) - Absorption
Rapidly absorbed following oral administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Sulfamethazine may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
- Affected organisms
- Not Available
- 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.
Drug Interaction Unlock Additional DataAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfamethazine. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfamethazine. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfamethazine. Alogliptin The therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfamethazine. Benzylpenicillin Sulfamethazine may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. Bromocriptine The therapeutic efficacy of Bromocriptine can be increased when used in combination with Sulfamethazine. Canagliflozin The therapeutic efficacy of Canagliflozin can be increased when used in combination with Sulfamethazine. Chlorpropamide The therapeutic efficacy of Chlorpropamide can be increased when used in combination with Sulfamethazine. Cholestyramine Cholestyramine can cause a decrease in the absorption of Sulfamethazine resulting in a reduced serum concentration and potentially a decrease in efficacy. Colesevelam Colesevelam can cause a decrease in the absorption of Sulfamethazine resulting in a reduced serum concentration and potentially a decrease in efficacy. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Sulfamethazine sodium 7Z13P9Q95C 1981-58-4 NGIVTUVVBWOTNT-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Trisulfaminic Sus Sulfamethazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfadiazine (167 mg) + Sulfamerazine (167 mg) Suspension Oral Shepherd Pharmaceuticals Inc. 1959-12-31 2001-04-11 Canada 
Trisulfaminic Tab Sulfamethazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfadiazine (167 mg) + Sulfamerazine (167 mg) Tablet Oral Shepherd Pharmaceuticals Inc. 1959-12-31 2001-04-11 Canada
Categories
- ATC Codes
- J01EB03 — Sulfadimidine
- J01EB — Short-acting sulfonamides
- 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
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Short-Acting Sulfonamides
- Sulfanilamides
- Sulfonamides
- SULFONAMIDES AND TRIMETHOPRIM
- Sulfones
- Sulfur Compounds
- 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
- sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:102265)
Chemical Identifiers
- UNII
- 48U51W007F
- CAS number
- 57-68-1
- InChI Key
- ASWVTGNCAZCNNR-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
- IUPAC Name
- 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide
- SMILES
- CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015522
- KEGG Compound
- C19530
- PubChem Compound
- 5327
- PubChem Substance
- 46507146
- ChemSpider
- 5136
- BindingDB
- 50238670
- 10178
- ChEBI
- 102265
- ChEMBL
- CHEMBL446
- ZINC
- ZINC000000057494
- Therapeutic Targets Database
- DAP001241
- PharmGKB
- PA451542
- Wikipedia
- Sulfamethazine
- MSDS
- Download (73 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- C.O. Truxton Inc.
- Spectrum Pharmaceuticals
- Dosage Forms
Form Route Strength Suspension Oral 86 mg/5mL Tablet Oral 167 mg Suspension Oral Tablet Oral - Prices
Unit description Cost Unit Sulfamethazine powder 1.74USD 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) 198.5 °C PhysProp water solubility 1500 mg/L (at 29 °C) MERCK INDEX (1983); at pH 7 logP 0.89 BIOBYTE (1995) pKa 7.59 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.23 mg/mL ALOGPS logP 0.43 ALOGPS logP 0.65 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 6.99 ChemAxon pKa (Strongest Basic) 2.04 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 73.38 m3·mol-1 ChemAxon Polarizability 28.8 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 + 0.9908 Blood Brain Barrier + 0.9275 Caco-2 permeable + 0.6203 P-glycoprotein substrate Non-substrate 0.8692 P-glycoprotein inhibitor I Non-inhibitor 0.888 P-glycoprotein inhibitor II Non-inhibitor 0.9281 Renal organic cation transporter Non-inhibitor 0.8643 CYP450 2C9 substrate Non-substrate 0.7791 CYP450 2D6 substrate Non-substrate 0.909 CYP450 3A4 substrate Non-substrate 0.7382 CYP450 1A2 substrate Non-inhibitor 0.9368 CYP450 2C9 inhibitor Non-inhibitor 0.8639 CYP450 2D6 inhibitor Non-inhibitor 0.9661 CYP450 2C19 inhibitor Non-inhibitor 0.9481 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8112 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.1354 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9434 hERG inhibition (predictor II) Non-inhibitor 0.8515
Spectra
- Mass Spec (NIST)
- Download (8.13 KB)
- Spectra
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
- Gene Name
- folP
- Uniprot ID
- P0AC13
- Uniprot Name
- Dihydropteroate synthase
- Molecular Weight
- 30614.855 Da
References
- Hong YL, Hossler PA, Calhoun DH, Meshnick SR: Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother. 1995 Aug;39(8):1756-63. [PubMed:7486915]
- Friaza V, Morilla R, Respaldiza N, de la Horra C, Calderon EJ: Pneumocystis jiroveci dihydropteroate synthase gene mutations among colonized individuals and Pneumocystis pneumonia patients from Spain. Postgrad Med. 2010 Nov;122(6):24-8. doi: 10.3810/pgm.2010.11.2219. [PubMed:21084778]
- Thijssen HH: A simplified radioassay method of dihydropteroate synthetase activity in Escherichia coli and its application for an inhibition study of p-aminobenzoi acid derivatives. Anal Biochem. 1973 Jun;53(2):579-85. [PubMed:4577373]
Enzymes
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the transfer of the acetyl group from acetyl coenzyme A to the free amino group of arylamines and hydrazines (PubMed:18795795). Is able to utilize not only acetyl-CoA, but also n-propionyl-CoA and acetoacetyl-CoA as acyl donors, although at a lower rate (PubMed:19014350). As acetyl-CoA and propionyl-CoA are products of cholesterol catabolism and the nat gene is likely present in the same operon than genes involved in cholesterol degradation, this enzyme could have a role in the utilization and regulation of these CoA species (PubMed:19014350).
- Specific Function
- Arylamine n-acetyltransferase activity
- Gene Name
- nat
- Uniprot ID
- P9WJI5
- Uniprot Name
- Arylamine N-acetyltransferase
- Molecular Weight
- 31028.88 Da
References
- Derewlany LO, Knie B, Koren G: Arylamine N-acetyltransferase activity of the human placenta. J Pharmacol Exp Ther. 1994 May;269(2):756-60. [PubMed:8182542]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216]
- Angelakou A, Valsami G, Koupparis M, Macheras P: Use of 1-anilino-8-napthalenesulphonate as an ion probe for the potentiometric study of the binding of sulphonamides to bovine serum albumin and plasma. J Pharm Pharmacol. 1993 May;45(5):434-8. [PubMed:8099962]
Drug created on August 29, 2007 08:54 / Updated on June 12, 2020 10:51