Identification
- Summary
Sulfamethizole is a sulfonamide antibiotic used to treat a wide variety of susceptible bacterial infections.
- Brand Names
- Urobiotic
- Generic Name
- Sulfamethizole
- DrugBank Accession Number
- DB00576
- Background
A sulfathiazole antibacterial agent.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Sulfamethizole (DB00576)
- Weight
- Average: 270.331
Monoisotopic: 270.024516964 - Chemical Formula
- C9H10N4O2S2
- Synonyms
- Sulfamethizol
- Sulfaméthizol
- Sulfamethizole
- Sulfamethizolum
- Sulfamethylthiadiazole
- Sulfametizol
Pharmacology
- Indication
For the treatment of urinary tract infection
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Cystitis Combination Product in combination with: Phenazopyridine (DB01438), Tetracycline (DB00759) •••••••••••• ••••••• Used in combination to treat Genital tract inflammation Combination Product in combination with: Phenazopyridine (DB01438), Tetracycline (DB00759) •••••••••••• ••••••• Used in combination to treat Gonorrhea Combination Product in combination with: Tetracycline (DB00759), Phenazopyridine (DB01438) •••••••••••• ••••••• Used in combination to treat Nephritis Combination Product in combination with: Phenazopyridine (DB01438), Tetracycline (DB00759) •••••••••••• ••••••• Used in combination to treat Nephritis Combination Product in combination with: Phenazopyridine (DB01438), Tetracycline (DB00759) •••••••••••• ••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Sulfamethizole 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
Sulfamethizole is a competitive inhibitor of bacterial enzyme dihydropteroate synthetase. The normal para-aminobenzoic acid (PABA) substrate is prevented from binding. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Target Actions Organism ADihydropteroate synthase inhibitorEscherichia coli (strain K12) - Absorption
Rapidly absorbed.
- Volume of distribution
Not Available
- Protein binding
98-99%
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
3-8 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your softwareAbrocitinib The metabolism of Abrocitinib can be decreased when combined with Sulfamethizole. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfamethizole. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Sulfamethizole. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfamethizole. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Sulfamethizole. - Food Interactions
- Take separate from meals. Take Urobiotic at least 1 hour before or 2 hours after eating.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Lucosil (Recip) / Rufol (Urgo) / Thiosulfil / Thiosulfil Forte
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Urobiotic Sulfamethizole (250 mg/1) + Oxytetracycline hydrochloride (250 mg/1) + Phenazopyridine hydrochloride (50 mg/1) Capsule Oral Roerig 2005-12-14 Not applicable US 
ซีโต้มัยซิน ชนิดแค๊ปซูล Sulfamethizole (250 MG) + Phenazopyridine (50 MG) + Tetracycline (250 MG) Capsule บริษัท ปัจจุบันโอสถ จำกัด จำกัด 1986-03-07 Not applicable Thailand 
Categories
- ATC Codes
- J01EB02 — Sulfamethizole
- J01EB — Short-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- B05CA — Antiinfectives
- B05C — IRRIGATING SOLUTIONS
- B05 — BLOOD SUBSTITUTES AND PERFUSION SOLUTIONS
- B — BLOOD AND BLOOD FORMING ORGANS
- 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-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Benzene Derivatives
- Benzenesulfonamides
- Blood and Blood Forming Organs
- Blood Substitutes and Perfusion Solutions
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Irrigating Solutions
- Ophthalmologicals
- Sensory Organs
- Short-Acting Antibacterial Sulfonamides
- Sulfanilamides
- Sulfathiazoles
- Sulfonamide Antibacterial
- Sulfonamides
- Sulfonamides and trimethoprim
- Sulfones
- Sulfur Compounds
- Thiazoles
- 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 / Organosulfonamides / Thiadiazoles / 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 / Azole / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative show 13 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfonamide, thiadiazoles, sulfonamide antibiotic (CHEBI:9331)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 25W8454H16
- CAS number
- 144-82-1
- InChI Key
- VACCAVUAMIDAGB-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)
- IUPAC Name
- 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
- SMILES
- CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1
References
- General References
- Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. [Article]
- Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. [Article]
- Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. [Article]
- External Links
- Human Metabolome Database
- HMDB0014715
- KEGG Drug
- D00870
- KEGG Compound
- C08050
- PubChem Compound
- 5328
- PubChem Substance
- 46508656
- ChemSpider
- 5137
- BindingDB
- 50295558
- 10179
- ChEBI
- 9331
- ChEMBL
- CHEMBL1191
- ZINC
- ZINC000000057493
- Therapeutic Targets Database
- DAP001202
- PharmGKB
- PA164781307
- Wikipedia
- Sulfamethizole
- MSDS
- Download (73.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 0 Terminated Treatment Osteomyelitis 1
Pharmacoeconomics
- Manufacturers
- Forest pharmaceuticals inc
- Wyeth ayerst laboratories
- Packagers
- Prescript Pharmaceuticals
- Professional Co.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Tablet Tablet Capsule, coated Oral 500 mg Capsule Oral Capsule - Prices
Unit description Cost Unit Methazolamide powder 27.0USD g Methazolamide 50 mg tablet 0.72USD tablet Neptazane 25 mg tablet 0.6USD tablet Methazolamide 25 mg tablet 0.48USD tablet 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) 208 °C PhysProp water solubility 1050 mg/L (at 37 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.54 HANSCH,C ET AL. (1995) logS -2.41 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.611 mg/mL ALOGPS logP 0.53 ALOGPS logP 0.21 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 6.71 Chemaxon pKa (Strongest Basic) 1.95 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 66.84 m3·mol-1 Chemaxon Polarizability 26.26 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 + 0.9604 Blood Brain Barrier + 0.9388 Caco-2 permeable - 0.8956 P-glycoprotein substrate Non-substrate 0.8662 P-glycoprotein inhibitor I Non-inhibitor 0.9232 P-glycoprotein inhibitor II Non-inhibitor 0.9308 Renal organic cation transporter Non-inhibitor 0.8833 CYP450 2C9 substrate Non-substrate 0.7992 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Non-substrate 0.7778 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9536 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8658 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8607 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.8636 Biodegradation Not ready biodegradable 0.9897 Rat acute toxicity 1.8564 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9357 hERG inhibition (predictor II) Non-inhibitor 0.9206
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 168.0345941 predictedDarkChem Lite v0.1.0 [M-H]- 168.0887941 predictedDarkChem Lite v0.1.0 [M-H]- 154.72482 predictedDeepCCS 1.0 (2019) [M+H]+ 169.7080941 predictedDarkChem Lite v0.1.0 [M+H]+ 169.2712941 predictedDarkChem Lite v0.1.0 [M+H]+ 157.08281 predictedDeepCCS 1.0 (2019) [M+Na]+ 168.5482941 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.4163941 predictedDarkChem Lite v0.1.0 [M+Na]+ 163.27934 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- The FDA label for dilantin, a CYP2C9 substrate, indicates that sulfamethizole may increase concentrations of dilantin (likely through CYP2C9 inhibition).
- 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. [Article]
- Jeffrey K. Aronson (2009). Meyler's Side Effects of Antimicrobial Drugs. Elsevier.
- FDA label, Dilantin [File]
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
- Brodersen R, Honore B: Drug binding properties of neonatal albumin. Acta Paediatr Scand. 1989 May;78(3):342-6. [Article]
- Agren A, Elofsson R, Meresaar U, Nilsson SO: Complex formation between macromolecules and drugs. 3. A study of the influence of ionic strength and pH. Binding between Aptin, nortriptyline, sulfamethizole or tripelenamine and serum albumin, poly-arginine, poly-lysine, poly-ornithine, protamine or dextran sulfate. Acta Pharm Suec. 1970 Apr;7(2):105-12. [Article]
- Nakano NI, Shimamori Y, Yamaguchi S: Mutual displacement interactions in the binding of two drugs to human serum albumin by frontal affinity chromatography. J Chromatogr. 1980 Feb 1;188(2):347-56. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:52