Summary: Sulfanilamides consisting of a 4-aminobenzenesulfonamido group at the 2-position of 1,3-thiazole. They are often used as ANTI-INFECTIVE AGENTS.

Top Publications

  1. Hu Y, Macfhionnghaile P, Caron V, Tajber L, Healy A, Erxleben A, et al. Formation, physical stability, and quantification of process-induced disorder in cryomilled samples of a model polymorphic drug. J Pharm Sci. 2013;102:93-103 pubmed publisher
    ..The calibration models had root mean square error of prediction values of <2.0% and were applied to quantify the extent of crystalline disorder during cryomilling. ..
  2. Ebrahimi H, Hadi J, Almayah A, Bolandnazar Z, Swadi A, Ebrahimi A. Metal-based biologically active azoles and β-lactams derived from sulfa drugs. Bioorg Med Chem. 2016;24:1121-31 pubmed publisher
    ..It has been shown that the metal complexes have significantly higher activity than corresponding ligands due to chelation process which reduces the polarity of metal ion by coordinating with ligands. ..
  3. Richter M, Sander M, Krauss M, Christl I, Dahinden M, Schneider M, et al. Cation binding of antimicrobial sulfathiazole to leonardite humic acid. Environ Sci Technol. 2009;43:6632-8 pubmed
    ..08 log (L mol(-1)) and log K(STA+,2) = 8.76 +/- 0.11 log (L mol(-1)), respectively). High affinity cation binding explains sorption of polar sulfonamides in agricultural soils and the strong dependence of sorption on SOM content and pH. ..
  4. Muster T, Prestidge C. Application of time-dependent sessile drop contact angles on compacts to characterise the surface energetics of sulfathiazole crystals. Int J Pharm. 2002;234:43-54 pubmed
    ..This study has led to an improved understanding of the influence of physical heterogeneities and the face-specific surface chemistry of individual crystals on the wetting characteristics of pharmaceutical compacts. ..
  5. Lotti T, Cordola M, Kleerebezem R, Caffaz S, Lubello C, van Loosdrecht M. Inhibition effect of swine wastewater heavy metals and antibiotics on anammox activity. Water Sci Technol. 2012;66:1519-26 pubmed publisher
    ..However, in order to verify the effect of these compounds on the growth of anammox bacteria, continuous culture experiments could be conducted. ..
  6. Angius F, Piras E, Uda S, Madeddu C, Serpe R, Bigi R, et al. Antimicrobial sulfonamides clear latent Kaposi sarcoma herpesvirus infection and impair MDM2-p53 complex formation. J Antibiot (Tokyo). 2017;70:962-966 pubmed publisher
    ..These findings detected a new molecular target for the activity of sulfonamides and offer a new potential perspective for treating KSHV-induced lymphoproliferative diseases. ..
  7. Clark S, Turnipseed S, Madson M, Hurlbut J, Kuck L, Sofos J. Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry. J AOAC Int. 2005;88:736-43 pubmed
    ..5, 5, and 10 ppb sulfonamides. This method was applied to imported flavored and unflavored condensed milk and cream cheese bars. The presence of STZ and SMZ residues was confirmed in 3 out of 6 products. ..
  8. Park K, Kwak I. Gene expression of ribosomal protein mRNA in Chironomus riparius: effects of endocrine disruptor chemicals and antibiotics. Comp Biochem Physiol C Toxicol Pharmacol. 2012;156:113-20 pubmed publisher
    ..Only RpS3 gene expression was up-regulated significantly in response to EDCs and fenbendazole. However, the C. riparius ribosomal proteins showed a limited response to cellular stress, following exposure to EDCs and VAs. ..
  9. Patel A, Luner P, Kemper M. Low-level determination of polymorph composition in physical mixtures by near-infrared reflectance spectroscopy. J Pharm Sci. 2001;90:360-70 pubmed
    ..These studies indicate that NIRS is a precise and accurate quantitative tool for determination of polymorphs in the solid state, is comparable to other characterization techniques, and is more convenient to use than many other methods. ..

More Information


  1. Olsen L, Nielsen I, Zachariassen A, Sederberg Olsen J, Frimodt Moller N. Single-dose versus six-day therapy with sulfamethizole for asymptomatic bacteriuria during pregnancy. A prospective randomised study. Dan Med Bull. 1989;36:486-7 pubmed
    ..Single-dose treatment is not inferior to conventional therapy; future study is needed to find the best single-dose regimen. ..
  2. Liu X, Lee J, Ji K, Takeda S, Choi K. Potentials and mechanisms of genotoxicity of six pharmaceuticals frequently detected in freshwater environment. Toxicol Lett. 2012;211:70-6 pubmed publisher
    ..The data indicate that these pharmaceuticals induce the DNA damages that stall DNA replication, leading to chromosomal breaks as well as translesion DNA synthesis mediated mutagenesis in DT40 cells. ..
  3. Roberts R, Payne R, Rowe R. Mechanical property predictions for polymorphs of sulphathiazole and carbamazepine. Eur J Pharm Sci. 2000;9:277-83 pubmed
  4. Jornet D, González Martínez M, Puchades R, Maquieira A. Antibiotic immunosensing: determination of sulfathiazole in water and honey. Talanta. 2010;81:1585-92 pubmed publisher
  5. Shen T, Stieglmeier M, Dai J, Urich T, Schleper C. Responses of the terrestrial ammonia-oxidizing archaeon Ca. Nitrososphaera viennensis and the ammonia-oxidizing bacterium Nitrosospira multiformis to nitrification inhibitors. FEMS Microbiol Lett. 2013;344:121-9 pubmed publisher
    ..Our results reflect the fundamental metabolic and cellular differences of AOA and AOB and will be useful for future applications of inhibitors aimed at distinguishing activities of AOA and AOB in soil environments...
  6. Davis J, Truman C, Kim S, Ascough J, Carlson K. Antibiotic Transport via Runoff and Soil Loss. J Environ Qual. 2006;35:2250-60 pubmed
    ..Other methods will be needed to reduce transport of other antibiotics. ..
  7. Caron V, Tajber L, Corrigan O, Healy A. A comparison of spray drying and milling in the production of amorphous dispersions of sulfathiazole/polyvinylpyrrolidone and sulfadimidine/polyvinylpyrrolidone. Mol Pharm. 2011;8:532-42 pubmed publisher
    ..This last result showed that production of amorphous dispersions by co-milling can significantly enhance the dissolution of poorly soluble drugs to a similar magnitude as co-spray dried systems. ..
  8. Kwon J. Mobility of veterinary drugs in soil with application of manure compost. Bull Environ Contam Toxicol. 2011;87:40-4 pubmed publisher
    ..The results indicate that sulfonamides pose a high risk of ground and surface water contamination and tetracyclines have the potential to persist in soils with bioactive epimers. ..
  9. Gulkowska A, Krauss M, Rentsch D, Hollender J. Reactions of a sulfonamide antimicrobial with model humic constituents: assessing pathways and stability of covalent bonding. Environ Sci Technol. 2012;46:2102-11 pubmed publisher
    ..These processes could also hold true for soils, and a slow nonextractable residue formation with time could be related to a slow increase of the amount of covalently bound sulfonamide and the strength of bonding...
  10. Mari G, Iacono E, Toni F, Predieri P, Merlo B. Evaluation of the effectiveness of intrauterine treatment with formosulphathiazole of clinical endometritis in postpartum dairy cows. Theriogenology. 2012;78:189-200 pubmed publisher
    ..6 ± 3.5; P < 0.05) corresponding to endometritis. In the present study, a commercial formosulphatiazole preparation was as effective as cephapirin and more effective than placebo for the treatment of clinical endometritis. ..
  11. Morales R, Ortiz M, Sarabia L, Sánchez M. D-optimal designs and N-way techniques to determine sulfathiazole in milk by molecular fluorescence spectroscopy. Anal Chim Acta. 2011;707:38-46 pubmed publisher
    ..3 ?g L(-1) and the detection capability (CC?) is 106.5 ?g L(-1), with the probabilities of false noncompliance (?) and false compliance (?) equal to 5%. ..
  12. Bianco S, Caron V, Tajber L, Corrigan O, Nolan L, Hu Y, et al. Modification of the solid-state nature of sulfathiazole and sulfathiazole sodium by spray drying. AAPS PharmSciTech. 2012;13:647-60 pubmed publisher
    ..This study indicated that control of processing and storage parameters can be exploited to produce drugs with a specific/desired solid-state nature. ..
  13. Richter M, Focks A, Siegfried B, Rentsch D, Krauss M, Schwarzenbach R, et al. Identification and dynamic modeling of biomarkers for bacterial uptake and effect of sulfonamide antimicrobials. Environ Pollut. 2013;172:208-15 pubmed publisher
    ..The EC value for the inhibition of pABA increase was 6.9 ± 0.7 ?mol L(-1) STA, which is similar to that calculated from optical density dynamics indicating that pABA is a direct biomarker for the SA effect. ..
  14. Kornfeld O, Nichols B. Vitamin B3 confers resistance to sulfa drugs in Saccharomyces cerevisiae. FEMS Microbiol Lett. 2005;251:137-41 pubmed
    ..carinii. We propose a model of metabolic rerouting in which increased nicotinate leads to increased intracellular concentration of p-aminobenzoate, thus leading to sulfonamide resistance. ..
  15. Brophy M, Deasy P. Egg albumin microspheres containing sulphamethizole. J Microencapsul. 1984;1:157-68 pubmed
    ..Cross-linking of the matrix with aldehydes or by gamma-irradiation proved unsatisfactory. ..
  16. Zheng H, Wang P, Li J. [Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography]. Se Pu. 2007;25:238-40 pubmed
    ..9%, respectively. Relative standard deviations were less than 10%. Routine tests show that the method is simple, fast, and has a good separation efficiency. It can be routinely used for the determination of these SAs in cosmetics. ..
  17. Lewandowski R, Grzybowski J, Głowińska E, Stozkowska W. [Effect of cerium nitrate supplementation to silver sulfathiazole preparations on survival of planctonic and attached to the dermis Staphylococcus aureus cells]. Wiad Lek. 2004;57:327-30 pubmed
    ..Kinetics of the release of chemotherapeutic compounds incorporated into a collagen dressing was the most effective for the combination of silver sulfathiazole with cerium nitrate. ..
  18. Wong T, Chan L, Lee H, Heng P. Release characteristics of pectin microspheres prepared by an emulsification technique. J Microencapsul. 2002;19:511-22 pubmed
    ..The extent of drug-pectin interaction was highest in microspheres containing sulphanilamide, followed by sulphaguanidine and sulphathiazole, opposite to that of drug content. ..
  19. Garoma T, Umamaheshwar S, Mumper A. Removal of sulfadiazine, sulfamethizole, sulfamethoxazole, and sulfathiazole from aqueous solution by ozonation. Chemosphere. 2010;79:814-20 pubmed publisher
    ..It was also observed that increasing the pH from 2.0 to 10.0 resulted in enhanced removal of the sulfonamides. ..
  20. Ji K, Choi K, Lee S, Park S, Khim J, Jo E, et al. Effects of sulfathiazole, oxytetracycline and chlortetracycline on steroidogenesis in the human adrenocarcinoma (H295R) cell line and freshwater fish Oryzias latipes. J Hazard Mater. 2010;182:494-502 pubmed publisher
    ..Thus, it is unlikely that these pharmaceuticals are causing adverse effects on fish in those rivers. ..
  21. Uthus E, Poellot R. Dietary nickel and folic acid interact to affect folate and methionine metabolism in the rat. Biol Trace Elem Res. 1997;58:25-33 pubmed
    ..Possibly the physiological function of nickel could be related to the tissue concentration of 5-methyltetrahydrofolate (MTHF) or tetrahydrofolate (THF). ..
  22. Wu Y, Zhao L, Liu Y, Jiang Y, Liu X, Shen J. [Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography]. Se Pu. 2007;25:728-31 pubmed
    ..1% and 88.3%. The relative standard deviations were between 2.3% and 5.0%. The detection limits were 1.7 - 2.8 microg/L, and the quantification limits wer 5.7 - 9.2 microg/L. ..
  23. Niu X, Glady Croué J, Croue J. Photodegradation of sulfathiazole under simulated sunlight: Kinetics, photo-induced structural rearrangement, and antimicrobial activities of photoproducts. Water Res. 2017;124:576-583 pubmed publisher
    ..The mass spectrometry and mechanistic work described here are new insights into the photochemistry of sulfonamides. ..
  24. Picker Freyer K, Liao X, Zhang G, Wiedmann T. Evaluation of the compaction of sulfathiazole polymorphs. J Pharm Sci. 2007;96:2111-24 pubmed
    ..However, in this system, there was little correspondence between the macroscopic and microscopic measurements, and thus particle-particle interactions may to be of paramount importance. ..
  25. Vedantam G, Guay G, Austria N, Doktor S, Nichols B. Characterization of mutations contributing to sulfathiazole resistance in Escherichia coli. Antimicrob Agents Chemother. 1998;42:88-93 pubmed
    ..An additional mutation contributing to sulfathiazole resistance, sux, has also been identified and has been shown to affect the histidine response to adenine sensitivity displayed by these purU strains. ..
  26. Jung J, Kim Y, Kim J, Jeong D, Choi K. Environmental levels of ultraviolet light potentiate the toxicity of sulfonamide antibiotics in Daphnia magna. Ecotoxicology. 2008;17:37-45 pubmed
    ..This study suggests that without taking into account the effects of UV irradiation, it is possible to underestimate the actual consequences of phototoxic sulfonamide antibiotics in the aquatic environment. ..
  27. Gift A, Luner P, Luedeman L, Taylor L. Manipulating hydrate formation during high shear wet granulation using polymeric excipients. J Pharm Sci. 2009;98:4670-83 pubmed publisher
    ..There was also evidence from physical property testing that the inclusion of a small amount of inhibitory polymer did not significantly change the compaction or flow behavior of the final granulation. ..
  28. Katayama K, Ohtani H, Murai A, Kakemi M, Koizumi T. Kinetic studies on drug disposition in rabbits. II. Dose dependent pharmacokinetics of sulfamethizole. J Pharmacobiodyn. 1990;13:108-19 pubmed
    ..The tissue distribution study contributed significantly to the understanding of the dose-dependent drug kinetics. ..
  29. Esrafili M, Behzadi H, Beheshtian J, Hadipour N. Theoretical 14N nuclear quadrupole resonance parameters for sulfa drugs: sulfamerazine and sulfathiazole. J Mol Graph Model. 2008;27:326-31 pubmed publisher
    ..N and N-H...O bond critical points, rho(b)(r(cp)), is observed. ..
  30. Wlodarczyk B, Spiegelstein O, Hill D, Le X, Finnell R. Arsenic urinary speciation in Mthfr deficient mice injected with sodium arsenate. Toxicol Lett. 2012;215:214-8 pubmed publisher
    ..The current data suggest that both the Mthfr status and food folate level modulate in a significant manner excretion of arsenic in mice, following intraperitoneal administration of sodium arsenate. ..
  31. Climent E, Bernardos A, Martínez Máñez R, Maquieira A, Marcos M, Pastor Navarro N, et al. Controlled delivery systems using antibody-capped mesoporous nanocontainers. J Am Chem Soc. 2009;131:14075-80 pubmed publisher
    ..This delivery behavior was compared with that shown by other solids that were prepared as models to assess the effect of the hapten and its interaction with antibody in the dye delivery control in the presence of the antigen. ..
  32. Silvestri R, Jensen W, Zibrak J, Alexander R, Rose R. Pulmonary infiltrates and hypoxemia in patients with the acquired immunodeficiency syndrome re-exposed to trimethoprim-sulfamethoxazole. Am Rev Respir Dis. 1987;136:1003-4 pubmed
    ..This reaction can mimic sepsis or the clinical worsening of underlying pulmonary opportunistic infection. The literature concerning adverse pulmonary effects of trimethoprim-sulfamethoxazole is reviewed. ..
  33. Hooton J, German C, Davies M, Roberts C. A comparison of morphology and surface energy characteristics of sulfathiazole polymorphs based upon single particle studies. Eur J Pharm Sci. 2006;28:315-24 pubmed
  34. Bianco S, Tewes F, Tajber L, Caron V, Corrigan O, Healy A. Bulk, surface properties and water uptake mechanisms of salt/acid amorphous composite systems. Int J Pharm. 2013;456:143-52 pubmed publisher
    ..Tuning the properties of amorphous salt/acid composites by optimising the ratio appears potentially promising to improve the physical stability of amorphous formulations. ..
  35. Kahle M, Stamm C. Time and pH-dependent sorption of the veterinary antimicrobial sulfathiazole to clay minerals and ferrihydrite. Chemosphere. 2007;68:1224-31 pubmed
    ..This implies that in many topsoils and sediments inorganic sorbents play a minor role. Our results highlight the need to account for contact time and speciation when predicting sulfonamide sorption in the environment. ..
  36. Kahle M, Stamm C. Sorption of the veterinary antimicrobial sulfathiazole to organic materials of different origin. Environ Sci Technol. 2007;41:132-8 pubmed
    ..Forthe cations, sorption followed the cation exchange capacities of the sorbents. STA sorption to manure and humic acid increased with higher ionic strength (0.31 M compared to 0.06 M) at pH 7.5. ..
  37. Pastor Navarro N, García Bover C, Maquieira A, Puchades R. Specific polyclonal-based immunoassays for sulfathiazole. Anal Bioanal Chem. 2004;379:1088-99 pubmed
    ..The selectivity and sensitivity (IC(50)=1.6 ng mL(-1)) make it a suitable screening method for determination of low levels of STZ in food samples. ..
  38. Cui Y, Zhang H, Ma Y, Dai C, Cui J. [Synthesis and identification of artificial antigens for sulfaguanidine and sulfathiazole]. Wei Sheng Yan Jiu. 2010;39:440-3 pubmed
    ..The antigens for sulfaguanidine and sulfathiazole were acquired successfully. The results have laid basis for the specific immunoassay of sulfaguanidine and sulfathiazole. ..
  39. Patel V, Dave R. Evaluation of colloidal solid dispersions: physiochemical considerations and in vitro release profile. AAPS PharmSciTech. 2013;14:620-8 pubmed publisher
    ..Thus, the porous silicon dioxide incorporated into the conventional binary solid dispersion acted as a carrier to disperse the complex and increase the dissolution rate. ..
  40. Yossa R, Sarker P, Vandenberg G. Preliminary evidence of the contribution of the intestinal microflora to biotin supply in zebrafish Danio rerio (Hamilton-Buchanan). Zebrafish. 2011;8:221-7 pubmed publisher
    ..Intestinal microbial synthesis is assumed to be a significant source of biotin to the zebrafish, as fish fed the antibiotic-supplemented diet showed the lowest growth, health condition, and feed utilization. ..
  41. Abu Bakar M, Nagy Z, Rielly C, Dann S. Investigation of the riddle of sulfathiazole polymorphism. Int J Pharm. 2011;414:86-103 pubmed publisher
    ..The properties of the obtained crystals, examined using various characterisation methods, are also presented and whenever possible, are compared with those of other workers. ..
  42. Wammer K, LaPara T, McNeill K, Arnold W, Swackhamer D. Changes in antibacterial activity of triclosan and sulfa drugs due to photochemical transformations. Environ Toxicol Chem. 2006;25:1480-6 pubmed
    ..The rapid screening method used for these two classes of compounds will be useful for helping to identify photolabile antibacterial compounds, for which photoproducts could require further investigation. ..
  43. Häkkinen A, Pöllänen K, Karjalainen M, Rantanen J, Louhi Kultanen M, Nyström L. Batch cooling crystallization and pressure filtration of sulphathiazole: the influence of solvent composition. Biotechnol Appl Biochem. 2005;41:17-28 pubmed
    ..51-0.63), which were accompanied with low average specific cake resistances [(8.7 x 10(7))-(1.2 x 10(9)) m/kg]. ..
  44. Luner P, Majuru S, Seyer J, Kemper M. Quantifying crystalline form composition in binary powder mixtures using near-infrared reflectance spectroscopy. Pharm Dev Technol. 2000;5:231-46 pubmed
    ..This study demonstrates that NIRS can be used as a quantitative physical characterization method, is comparable in accuracy to other techniques, and is capable of detecting low levels of one crystal form in the presence of another. ..
  45. Sumano H, Gutierrez L, Zamora M, Perez M, Cruz C. Serum activity/concentration profiles of a sustained-released formulation of sulphathiazole-trimethoprim (2.5:1) in calves. Vet Rec. 2004;155:672-4 pubmed
    ..25 microg/ml in group B and 8.01 microg/ml in group C. The mean areas under the curves of the serum activity time curves were 838 microg/ml/hour in group A, 216 microg/ml/hour in group B and 182 microg/ml/hour in group C. ..
  46. Boldyrev V, Shakhtshneider T, Chizhik S. On the mechanism of solubilization of drugs in the presence of poorly soluble additives. Int J Pharm. 2005;295:177-82 pubmed
  47. Kragh Hansen U. Evidence for a large and flexible region of human serum albumin possessing high affinity binding sites for salicylate, warfarin, and other ligands. Mol Pharmacol. 1988;34:160-71 pubmed
    ..However, the data also showed that other attractive forces must be operative as well. ..
  48. Wong T, Chan L, Kho S, Sia Heng P. Design of controlled-release solid dosage forms of alginate and chitosan using microwave. J Control Release. 2002;84:99-114 pubmed
    ..The results showed that microwave technology can be employed in the design of solid dosage forms for controlled-release application without the use of noxious chemical agents. ..
  49. Gonzalez Alvarez M, Alzuet G, Borras J, Macias B, del Olmo M, Liu Gonzalez M, et al. Nuclease activity of [Cu(sulfathiazolato)(2)(benzimidazole)(2)]2MeOH. Synthesis, properties and crystal structure. J Inorg Biochem. 2002;89:29-35 pubmed
    ..The efficiency of cleavage reaction of the title compound with pUC18 and with different reducing agents follows the order ascorbate-H(2)O(2)>ascorbate>MPA>dithiothreitol>H(2)O(2). ..
  50. Kordikowski A, Shekunov T, York P. Polymorph control of sulfathiazole in supercritical CO2. Pharm Res. 2001;18:682-8 pubmed
    ..The crystallization method developed proved to be a simple and efficient technique for reproducible and consistent isolation of sulfathiazole polymorphs. ..
  51. Wan L, Chui W. Deviation of the ratio of drugs in a two-component mixture encapsulated in cellulose phthalate microspheres. J Microencapsul. 1995;12:417-23 pubmed
    ..When more than one drug is required to be microencapsulated, the drug ratio may change if the drugs have different solubility in acetic acid. ..
  52. Zeitler J, Newnham D, Taday P, Threlfall T, Lancaster R, Berg R, et al. Characterization of temperature-induced phase transitions in five polymorphic forms of sulfathiazole by terahertz pulsed spectroscopy and differential scanning calorimetry. J Pharm Sci. 2006;95:2486-98 pubmed
    ..The phase transitions can be monitored by terahertz pulsed spectroscopy. Polymorphic impurities of the samples can be detected in the room temperature spectra and their effect on the phase transition behavior can be studied. ..
  53. Dave R, Patel H, DONAHUE E, Patel A. To evaluate the change in release from solid dispersion using sodium lauryl sulfate and model drug sulfathiazole. Drug Dev Ind Pharm. 2013;39:1562-72 pubmed publisher
    ..The solubilization mechanism is mainly responsible for this higher dissolution rate when we incorporate the SLS in SD. ..