Identification
- Generic Name
- Sulfathiazole
- DrugBank Accession Number
- DB06147
- Background
Sulfathiazole is a short-acting sulfa drug. It used to be a common oral and topical antimicrobial until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide.
Except for those formulated for vaginal use, the FDA withdrew its approval for the use of all drug products containing sulfathiazole.1
- Type
- Small Molecule
- Groups
- Approved, Vet approved, Withdrawn
- Structure
Structure for Sulfathiazole (DB06147)
- Weight
- Average: 255.317
Monoisotopic: 255.013617927 - Chemical Formula
- C9H9N3O2S2
- Synonyms
- 2-(p-Aminobenzenesulfonamido)thiazole
- 2-(p-Aminobenzenesulphonamido)thiazole
- 2-(Sulfanilylamino)thiazole
- 2-Sulfanilamidothiazol
- 2-Sulfanilamidothiazole
- 2-Sulfonamidothiazole
- 4-Amino-N-2-thiazolylbenzenesulfonamide
- N(1)-2-Thiazolylsulfanilamide
- N1-2-Thiazolylsulfanilamide
- Sulfanilamidothiazole
- Sulfathiazol
- Sulfathiazole
- Sulfathiazolum
- Sulfatiazol
- Sulphathiazole
Pharmacology
- Indication
Sulfathiazole is effective against a wide range of gram positive and gram negative pathogenic microorganisms. Although no longer used in humans, it is used in cattle.
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 Bacterial enteritis Combination Product in combination with: Sulfamerazine (DB01581), Sulfadiazine (DB00359) •••••••••••• •••••• Used in combination to treat Ear infection bacterial Combination Product in combination with: Sulfamerazine (DB01581), Sulfadiazine (DB00359) •••••••••••• •••••• Used in combination to treat Ear infection bacterial Combination Product in combination with: Sulfadiazine (DB00359), Sulfamerazine (DB01581) •••••••••••• •••••• Used in combination to treat Enteritis Combination Product in combination with: Sulfadiazine (DB00359), Sulfamerazine (DB01581) •••••••••••• •••••• Used in combination to treat Eye infections Combination Product in combination with: Sulfadiazine (DB00359), Sulfamerazine (DB01581) •••••••••••• •••••• - 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
Not Available
- Mechanism of action
Target Actions Organism ADihydropteroate synthetase inhibitorPlasmodium falciparum - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Metabolism of sulfonamide drugs in animals includes conjugation at the N4-position (acetyl, sulfate, glucuronic acid, and glucose), conjugation at the N1-position (sulfate and glucuronic acid), removal of the p-amino group (formation of the desamino metabolite), ring hydroxylation, and conjugation of the ring hydroxylation products. Dietary nitrite enhances the production of the desamino metabolite of sulfathiazole. The intermediate leading to the desamino metabolite of sulfamethazine is weakly mutagenic in the Ames test (Nelson et al., 1987; Paulson et al., 1987).
- Route of elimination
Not Available
- Half-life
Not Available
- 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
Acute oral toxicity (LD50): 4500 mg/kg [Mouse].
- 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 softwareBenzylpenicillin Sulfathiazole may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. Chloroprocaine The therapeutic efficacy of Sulfathiazole can be decreased when used in combination with Chloroprocaine. Insulin aspart The risk or severity of hypoglycemia can be increased when Sulfathiazole is combined with Insulin aspart. Insulin beef The risk or severity of hypoglycemia can be increased when Sulfathiazole is combined with Insulin beef. Insulin degludec The risk or severity of hypoglycemia can be increased when Sulfathiazole is combined with Insulin degludec. - Food Interactions
- No interactions found.
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.- Product Ingredients
Ingredient UNII CAS InChI Key Sulfathiazole sodium PV16N742VM 144-74-1 IMPWUOJNMQNKON-UHFFFAOYSA-N - International/Other Brands
- Norsulfazolum (Galen) / Sulfatiazol (Fecofar)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Gyne-Sulf Sulfathiazole (3.42 g/100g) + Sulfabenzamide (3.7 g/100g) + Sulfacetamide (2.86 g/100g) Cream Vaginal GW Laboratories, Inc. 1983-08-03 1995-09-01 US 
Triple Sulfa Sulfathiazole (3.42 g/100g) + Sulfabenzamide (3.7 g/100g) + Sulfacetamide (2.86 g/100g) Cream Vaginal Physicians Total Care, Inc. 1989-02-01 2004-06-30 US
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- J01EB — Short-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Benzene Derivatives
- Benzenesulfonamides
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Short-Acting Antibacterial Sulfonamides
- Sulfanilamides
- Sulfathiazoles
- 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 / Thiazoles / 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
- substituted aniline, sulfonamide, 1,3-thiazole, sulfonamide antibiotic (CHEBI:9337) / a small molecule (CPD-11285)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Y7FKS2XWQH
- CAS number
- 72-14-0
- InChI Key
- JNMRHUJNCSQMMB-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)
- IUPAC Name
- 4-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide
- SMILES
- NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CS1
References
- General References
- Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
- External Links
- Human Metabolome Database
- HMDB0015619
- KEGG Drug
- D01047
- KEGG Compound
- C11169
- PubChem Compound
- 5340
- PubChem Substance
- 175427054
- ChemSpider
- 5148
- BindingDB
- 50027796
- 10193
- ChEBI
- 9337
- ChEMBL
- CHEMBL437
- ZINC
- ZINC000000121458
- PharmGKB
- PA165958356
- PDBe Ligand
- YTZ
- Wikipedia
- Sulfathiazole
- PDB Entries
- 3tye / 4j7u / 5cp3 / 5g44
- MSDS
- Download (47 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Ointment Topical 5 g Cream Vaginal Ointment Topical Powder Topical Tablet 500 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 189 °C PhysProp water solubility 373 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.05 HANSCH,C ET AL. (1995) pKa 7.2 BUDAVARI,S ET AL. (1996) - Predicted Properties
Property Value Source Water Solubility 0.921 mg/mL ALOGPS logP 0.88 ALOGPS logP 0.98 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 6.93 Chemaxon pKa (Strongest Basic) 2.04 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 85.08 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 62.27 m3·mol-1 Chemaxon Polarizability 23.93 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 + 0.9087 Blood Brain Barrier + 0.946 Caco-2 permeable - 0.6975 P-glycoprotein substrate Non-substrate 0.9186 P-glycoprotein inhibitor I Non-inhibitor 0.9445 P-glycoprotein inhibitor II Non-inhibitor 0.8896 Renal organic cation transporter Non-inhibitor 0.8926 CYP450 2C9 substrate Non-substrate 0.8236 CYP450 2D6 substrate Non-substrate 0.9083 CYP450 3A4 substrate Non-substrate 0.7952 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9338 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7817 Ames test Non AMES toxic 0.9151 Carcinogenicity Non-carcinogens 0.9034 Biodegradation Not ready biodegradable 0.9776 Rat acute toxicity 1.7929 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9396 hERG inhibition (predictor II) Non-inhibitor 0.9101
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 159.6536402 predictedDarkChem Lite v0.1.0 [M-H]- 159.8567402 predictedDarkChem Lite v0.1.0 [M-H]- 152.80086 predictedDeepCCS 1.0 (2019) [M+H]+ 160.6658402 predictedDarkChem Lite v0.1.0 [M+H]+ 160.7476402 predictedDarkChem Lite v0.1.0 [M+H]+ 155.15887 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.6360402 predictedDarkChem Lite v0.1.0 [M+Na]+ 161.31227 predictedDeepCCS 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
- Nichols BP, Guay GG: Gene amplification contributes to sulfonamide resistance in Escherichia coli. Antimicrob Agents Chemother. 1989 Dec;33(12):2042-8. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Oxygen binding
- Specific Function
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Ji K, Choi K, Lee S, Park S, Khim JS, Jo EH, Choi K, Zhang X, Giesy JP: Effects of sulfathiazole, oxytetracycline and chlortetracycline on steroidogenesis in the human adrenocarcinoma (H295R) cell line and freshwater fish Oryzias latipes. J Hazard Mater. 2010 Oct 15;182(1-3):494-502. doi: 10.1016/j.jhazmat.2010.06.059. Epub 2010 Jun 19. [Article]
Drug created at November 19, 2007 17:59 / Updated at November 03, 2023 23:50