Summary: Compounds based on 4-aminobenzenesulfonamide. The '-anil-' part of the name refers to aniline.

Top Publications

  1. Vullo D, Nishimori I, Scozzafava A, Kohler S, Winum J, Supuran C. Inhibition studies of a beta-carbonic anhydrase from Brucella suis with a series of water soluble glycosyl sulfanilamides. Bioorg Med Chem Lett. 2010;20:2178-82 pubmed publisher
    ..been cloned, purified characterized kinetically and for inhibition with a series of water soluble glycosylated sulfanilamides. bsCA 1 has appreciable activity as catalyst for the hydration of CO(2) to bicarbonate, with a k(cat) of 6...
  2. Grandjean O, Vernoux T, Laufs P, Belcram K, Mizukami Y, Traas J. In vivo analysis of cell division, cell growth, and differentiation at the shoot apical meristem in Arabidopsis. Plant Cell. 2004;16:74-87 pubmed
    ..In this case, cell growth and, later, cell differentiation were inhibited, suggesting an important role for DNA synthesis in growth and patterning. ..
  3. Wiesler B, Wang Q, Nick P. The stability of cortical microtubules depends on their orientation. Plant J. 2002;32:1023-32 pubmed
    ..The results are discussed in terms of direction-dependent differences in the lifetime of microtubules...
  4. Zevzikoviene A, Zevzikovas A, Tarasevicius E, Pavlonis A, Dirse V. Synthesis and in vitro antimicrobial study of 4-thiazolidinone containing sulfanilamide. Acta Pol Pharm. 2012;69:911-5 pubmed
    ..pneumoniae, P. mirabilis, B. subtilis, B. cereus and C. albicans taking sulfadimidine, sulfathiazole, sulfanilamide and sulfamethizole as standard drugs. Synthesized compounds (2a-d) demonstrated selective activity against B. cereus. ..
  5. Bisgrove S, Kropf D. Cytokinesis in brown algae: studies of asymmetric division in fucoid zygotes. Protoplasma. 2004;223:163-73 pubmed
    ..Pharmacological agents were used to investigate the roles of microtubules, actin, and secretion in cytokinesis. The findings indicate a mechanism of cytokinesis that may be unique to the brown algae. ..
  6. Paredez A, Persson S, Ehrhardt D, Somerville C. Genetic evidence that cellulose synthase activity influences microtubule cortical array organization. Plant Physiol. 2008;147:1723-34 pubmed publisher
  7. Corson F, Hamant O, Bohn S, Traas J, Boudaoud A, Couder Y. Turning a plant tissue into a living cell froth through isotropic growth. Proc Natl Acad Sci U S A. 2009;106:8453-8 pubmed publisher
    ..If not, a "cell froth" very similar to that observed experimentally is obtained. Our results suggest strong physical constraints on the mechanisms of growth regulation. ..
  8. Hamant O, Heisler M, Jonsson H, Krupinski P, Uyttewaal M, Bokov P, et al. Developmental patterning by mechanical signals in Arabidopsis. Science. 2008;322:1650-5 pubmed publisher
  9. Yang D, Yan J, Xu J, Ye F, Zhou Z, Zhang W, et al. [Synthesis and investigation on antidiabetic activity of 4-(1-aryl-3-oxo-5-phenylpentylamino) benzenesulfonamide]. Yao Xue Xue Bao. 2010;45:66-71 pubmed
    ..The structure-activity relationship of these new beta-amino ketones containing benzenesulfonamide unit was also discussed preliminarily. ..

More Information


  1. Guastavino E, Litwin N, Heffes Nahmod L, Licastro R. [Ulcerative colitis in children. Levels of salicylazosulfapyridine and sulfapyridine during treatment]. Acta Gastroenterol Latinoam. 1988;18:107-13 pubmed
    ..There was no statistical correlation between doses and SP or SASP levels in this group, and the respective levels of SASP and SP at 6 and 12 hours after doses showed no significative differences.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  2. Demirdag R, Comakli V, Senturk M, Ekinci D, Irfan Kufrevioglu O, Supuran C. Purification and characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity. Bioorg Med Chem. 2013;21:1522-5 pubmed publisher
    ..348-69.31?m. ..
  3. Imoto Y, Kuroiwa H, Yoshida Y, Ohnuma M, Fujiwara T, Yoshida M, et al. Single-membrane-bounded peroxisome division revealed by isolation of dynamin-based machinery. Proc Natl Acad Sci U S A. 2013;110:9583-8 pubmed publisher
    ..These findings are useful for understanding the fundamental systems in eukaryotic cells. ..
  4. Trotta R, Brown M, Terrell J, Geyer J. Defective DNA repair as a potential mechanism for the rapid development of drug resistance in Plasmodium falciparum. Biochemistry. 2004;43:4885-91 pubmed
    ..We propose that altered DNA repair, either through defective repair mechanisms or drug-mediated inhibition, may contribute to the accelerated development of drug resistance in the parasite. ..
  5. Heming T, Stabenau E, Vanoye C, Moghadasi H, Bidani A. Roles of intra- and extracellular carbonic anhydrase in alveolar-capillary CO2 equilibration. J Appl Physiol (1985). 1994;77:697-705 pubmed
    ..min-1.Torr-1. The results indicate that extracellular vascular CA activity influences both diffusive and reactive CO2 equilibration. However, cytosolic CA has no detectable role in alveolar-capillary CO2 equilibration. ..
  6. Castrejon J, Lavergne S, El Sheikh A, Farrell J, Maggs J, Sabbani S, et al. Metabolic and chemical origins of cross-reactive immunological reactions to arylamine benzenesulfonamides: T-cell responses to hydroxylamine and nitroso derivatives. Chem Res Toxicol. 2010;23:184-92 pubmed publisher
    ..1 h. T-cell cross-reactivity with nitroso sulfonamides provides a mechanistic explanation as to why structurally related arylamine benzenesulfonamides are contraindicated in hypersensitive patients. ..
  7. Thiele Bruhn S. Microbial inhibition by pharmaceutical antibiotics in different soils--dose-response relations determined with the iron(III) reduction test. Environ Toxicol Chem. 2005;24:869-76 pubmed
    ..The microbial inhibition was influenced indirectly by the soil pH, which affects the ionization status of the amphoteric antibiotics. ..
  8. Gratacós Cubarsí M, Castellari M, Valero A, Garcia Regueiro J. A simplified LC-DAD method with an RP-C12 column for routine monitoring of three sulfonamides in edible calf and pig tissue. Anal Bioanal Chem. 2006;385:1218-24 pubmed
    ..Separation of some possible SMZ metabolites should be further investigated. ..
  9. Chakravarty S, Kannan K. Drug-protein interactions. Refined structures of three sulfonamide drug complexes of human carbonic anhydrase I enzyme. J Mol Biol. 1994;243:298-309 pubmed
    ..An important role of Thr199 in distinguishing between the substrate and inhibitor binding modes of HCO3- to the enzyme at high pH is also inferred. ..
  10. Blum J, Dosogne H, Hoeben D, Vangroenweghe F, Hammon H, Bruckmaier R, et al. Tumor necrosis factor-alpha and nitrite/nitrate responses during acute mastitis induced by Escherichia coli infection and endotoxin in dairy cows. Domest Anim Endocrinol. 2000;19:223-35 pubmed
    ..coli infection and endotoxin in lactating dairy cows is indicated, but could not be inhibited by antibiotic treatment. ..
  11. Zachariadis M, Quader H, Galatis B, Apostolakos P. Organization of the endoplasmic reticulum in dividing cells of the gymnosperms Pinus brutia and Pinus nigra, and of the pterophyte Asplenium nidus. Cell Biol Int. 2003;27:31-40 pubmed
    ..Observations made on P. nigra root-cells affected by oryzalin, colchicine and cytochalasin D favour the conclusion that the pattern of ER organization is controlled during mitosis and cytokinesis by the MT cytoskeleton. ..
  12. Haddow M, Gelbrich T, Griesser U. Similar sulfonamides with different crystal structures: sulfasymazine and sulfatriazine. Acta Crystallogr C. 2008;64:o309-12 pubmed publisher
    ..This study demonstrates the versatile nature of the hydrogen-bonding capabilities in sulfonamides, even in structurally very similar molecules. ..
  13. 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. ..
  14. Cross R, Smairl A. Salt effects in capillary zone electrophoresis. V. Adsorption and retention of electrically neutral analytes. J Chromatogr A. 2001;929:113-21 pubmed
    ..A mechanism for adsorption is proposed and the generality of the phenomenon is discussed. ..
  15. Ilies M, Vullo D, Pastorek J, Scozzafava A, Ilies M, Caproiu M, et al. Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives. J Med Chem. 2003;46:2187-96 pubmed
    Two series of halogenated sulfonamides have been prepared. The first consists of mono/dihalogenated sulfanilamides, whereas the second one consists of the mono/dihalogenated aminobenzolamides, incorporating equal or different halogens (F, ..
  16. Sugimoto K, Himmelspach R, Williamson R, Wasteneys G. Mutation or drug-dependent microtubule disruption causes radial swelling without altering parallel cellulose microfibril deposition in Arabidopsis root cells. Plant Cell. 2003;15:1414-29 pubmed
    ..Our results suggest that cortical microtubules regulate growth anisotropy by some mechanism other than cellulose microfibril alignment or synthesis. ..
  17. Shimamura M, Brown R, Lemmon B, Akashi T, Mizuno K, Nishihara N, et al. Gamma-tubulin in basal land plants: characterization, localization, and implication in the evolution of acentriolar microtubule organizing centers. Plant Cell. 2004;16:45-59 pubmed
    ..We conclude that gamma-tubulin is a highly conserved protein associated with microtubule nucleation in basal land plants and that it has a cell cycle-dependent distribution essential for the orderly succession of microtubule arrays...
  18. Bannigan A, Wiedemeier A, Williamson R, Overall R, Baskin T. Cortical microtubule arrays lose uniform alignment between cells and are oryzalin resistant in the Arabidopsis mutant, radially swollen 6. Plant Cell Physiol. 2006;47:949-58 pubmed
    ..The rsw6 mutant provides a unique tool with which to study the coordination of microtubule organization at a multicellular level. ..
  19. Luo X, Du C, Wei J, Deng J, Lin Y, Lin C. Study of the interaction between sodium salts of (2E)-3-(4'-halophenyl)prop-2-enoyl sulfachloropyrazine and bovine serum albumin by fluorescence spectroscopy. Luminescence. 2013;28:202-10 pubmed publisher
    ..The binding distances between CCSCPs and BSA were determined using the Förster non-radiation energy transfer theory and the effects of CCSCPs on the conformation of BSA were analyzed by synchronous fluorescence spectroscopy. ..
  20. Rodríguez Díaz J, Rosas Camargo V, Vega Vega O, Morales Espinosa D, Mendez Reguera A, Martínez Tlahuel J, et al. Clinical and pathological factors associated with the development of hepatocellular carcinoma in patients with hepatitis virus-related cirrhosis: a long-term follow-up study. Clin Oncol (R Coll Radiol). 2007;19:197-203 pubmed
    ..8%, respectively. We found three HCC-associated variables: histological activity, platelet count and alpha-fetoprotein levels. Patients considered as high risk for developing HCC must be considered candidates for closer follow-up. ..
  21. Shimada T, Yamamoto K, Ishihama A. Involvement of the leucine response transcription factor LeuO in regulation of the genes for sulfa drug efflux. J Bacteriol. 2009;191:4562-71 pubmed publisher
    ..The results described herein indicate that the yjcRQP operon, one of the LeuO targets, is involved in sensitivity control against sulfa drugs. We propose to rename the yjcRQP genes the sdsRQP genes (sulfa drug sensitivity determinant). ..
  22. 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. ..
  23. Sabot J, Bornet C, Favre S, Sabot Gueriaux S. The analysis of peculiar urinary (and other) calculi: an endless source of challenge. Clin Chim Acta. 1999;283:151-8 pubmed
    ..We conclude that the analysis of all calculi must be carried out, to determine their composition, and an efficient strategy must be used. ..
  24. Emi T, Kinoshita T, Sakamoto K, Mineyuki Y, Shimazaki K. Isolation of a protein interacting with Vfphot1a in guard cells of Vicia faba. Plant Physiol. 2005;138:1615-26 pubmed
    ..From these results, we conclude that VfPIP may act as a downstream component of phototropin (Vfphot1a) in blue light signaling in guard cells. The possible role of VfPIP in blue light signaling of guard cells is discussed...
  25. Khokhlova L, Olinevich O, Raudaskoski M. Reorganization of the microtubule and actin cytoskeleton in root cells of Triticum aestivum L during low temperature and abscisic acid treatments. Cell Biol Int. 2003;27:211-2 pubmed
  26. Miranda K, Espey M, Wink D. A rapid, simple spectrophotometric method for simultaneous detection of nitrate and nitrite. Nitric Oxide. 2001;5:62-71 pubmed
    ..This report introduces a new, convenient assay for the stable oxidation products of nitrogen oxide chemistry in biological samples. ..
  27. El Ghenymy A, Cabot P, Centellas F, Garrido J, Rodriguez R, Arias C, et al. Mineralization of sulfanilamide by electro-Fenton and solar photoelectro-Fenton in a pre-pilot plant with a Pt/air-diffusion cell. Chemosphere. 2013;91:1324-31 pubmed publisher
    ..The N content of sulfanilamide was mainly mineralized as NH?? ion and in much lesser extent as NO?? ion, whereas most of its initial S was converted into SO?²? ion. ..
  28. Henriquez F, Ingram P, Muench S, Rice D, Roberts C. Molecular basis for resistance of acanthamoeba tubulins to all major classes of antitubulin compounds. Antimicrob Agents Chemother. 2008;52:1133-5 pubmed
    ..are resistant to five antimicrotubule compounds, unlike any other eukaryote studied so far. Resistance correlates with critical amino acid differences within the inhibitor binding sites of the tubulin heterodimers. ..
  29. Peters N, Kropf D. Kinesin-5 motors are required for organization of spindle microtubules in Silvetia compressa zygotes. BMC Plant Biol. 2006;6:19 pubmed
    ..compressa likely organize microtubules at spindle poles. To our knowledge, this is the first functional characterization of the Kinesin-5 family in stramenopiles. ..
  30. Benbow J, Bernberg E, Korda A, Mead J. Synthesis and evaluation of dinitroanilines for treatment of cryptosporidiosis. Antimicrob Agents Chemother. 1998;42:339-43 pubmed
    ..Enhanced water solubility alone did not overcome the drug availability problem; however, several candidates with similar activities but with toxicities lower than those of the lead compounds were produced...
  31. Ohmachi Y, Toriumi W, Takashima K, Doi K. Systemic histopathology of rats treated with 6-sulfanilamidoindazole, a novel arthritogenic sulfonamide. Toxicol Pathol. 1998;26:262-70 pubmed
  32. Allum J, Bringloe D, Roberts A. Chromosome doubling in a Rosa rugosa Thunb. hybrid by exposure of in vitro nodes to oryzalin: the effects of node length, oryzalin concentration and exposure time. Plant Cell Rep. 2007;26:1977-84 pubmed
    ..This suggests that oryzalin diffused to the meristem mainly via the cut surfaces and that access via the epidermis and cuticle was impeded. ..
  33. Dieckmann A, Jung A. Stage-specific sensitivity of Plasmodium falciparum to antifolates. Z Parasitenkd. 1986;72:591-4 pubmed
    ..These results support earlier reports suggesting that DNA synthesis is most pronounced in 32-42 h old trophozoites. The possible relevance of our results to the metabolism of P. falciparum is discussed. ..
  34. Giustarini D, Rossi R, Milzani A, Dalle Donne I. Nitrite and nitrate measurement by Griess reagent in human plasma: evaluation of interferences and standardization. Methods Enzymol. 2008;440:361-80 pubmed publisher
  35. Meaney M, Fairweather I, Brennan G, Forbes A. Transmission electron microscope study of the ultrastructural changes induced in the tegument and gut of Fasciola hepatica following in vivo drug treatment with clorsulon. Parasitol Res. 2004;92:232-41 pubmed
    ..An increase in the number of autophagic vacuoles was evident, the mitochondria and the gER remained swollen and lipid droplets were present in the cells. ..
  36. Schreiber K, Ckurshumova W, Peek J, Desveaux D. A high-throughput chemical screen for resistance to Pseudomonas syringae in Arabidopsis. Plant J. 2008;54:522-31 pubmed publisher
    ..The whole-organism liquid assay provides a novel approach to probe chemical libraries in a high-throughput manner for compounds that reduce bacterial virulence in plants. ..
  37. George T, Endeshaw M, Morgan R, Mahasenan K, Delfin D, Mukherjee M, et al. Synthesis, biological evaluation, and molecular modeling of 3,5-substituted-N1-phenyl-N4,N4-di-n-butylsulfanilamides as antikinetoplastid antimicrotubule agents. Bioorg Med Chem. 2007;15:6071-9 pubmed
    ..7 microM). Computational studies provide a rationale for the antiparasitic order of activity of these analogues and further insight into the role of the substituents at the 3 and 5 positions of the sulfanilamide ring. ..
  38. Feng Y, Liao C, Shih K. Copper-promoted circumneutral activation of H2O2 by magnetic CuFe2O4 spinel nanoparticles: Mechanism, stoichiometric efficiency, and pathway of degrading sulfanilamide. Chemosphere. 2016;154:573-582 pubmed publisher
    ..The findings of this study suggest that copper can be used as a doping metal to improve the reactivity and expand the effective pH range of iron oxides. ..
  39. Takahashi T, Kamiya N, Kawabata N, Takagi M. The effect of retinoic acid on a zinc finger transcription factor, AJ18, during differentiation of a rat clonal preosteoblastic cell line, ROB-C20, into osteoblasts. Arch Oral Biol. 2008;53:87-94 pubmed
    ..This study supports the hypothesis that RA may restrict to the differentiation of C20 cells into mature osteoblasts via inductive AJ18 expression with activation of multiple signal pathways. ..
  40. Hurst H, Clothier R, Pratten M. An evaluation of the chick cardiomyocyte micromass system for identification of teratogens in a blind trial. Reprod Toxicol. 2009;28:503-10 pubmed publisher
    ..This approach revealed differential effects on contractility independent of effects on activity/viability, whilst the total cell protein remained unchanged. We suggest that pre-validation of this system should be examined...
  41. Stoeckel H, Takeda K. Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments?. Protoplasma. 2002;220:79-87 pubmed
    ..Microfilament-depolymerizing drugs shifted this proportion to about 12%, suggesting that microfilaments participate in the regulation of K(+) currents in tobacco 'Bright Yellow-2' cells. ..
  42. Zhang Y, Hu X, Chen J, Wu Z, Huang G, Hu Y, et al. [Efficacy and safety of azosemide in patients with edema and ascites]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2005;34:459-64 pubmed
    ..Azosemide could effectively lessen edema, improve heart function and decrease ascitesûit is well tolerated and is particularly useful for the diuretic treatment. ..
  43. Moore W, Kern J, Bhat R, Commons T, Fukayama S, Goljer I, et al. Modulation of Wnt signaling through inhibition of secreted frizzled-related protein I (sFRP-1) with N-substituted piperidinyl diphenylsulfonyl sulfonamides. J Med Chem. 2009;52:105-16 pubmed publisher
    ..Details of the structure-activity relationships and biological activity from the first structural class of this scaffold will be discussed. ..
  44. Thiry A, Delayen A, Goossens L, Houssin R, Ledecq M, Frankart A, et al. Synthesis and biological evaluation of a new family of anti-benzylanilinosulfonamides as CA IX inhibitors. Eur J Med Chem. 2009;44:511-8 pubmed publisher
    ..A molecular modeling study was conducted in order to simulate the binding mode of this new family of enzyme inhibitors within the active sites of hCA IX and hCA II. ..
  45. Bos M, Sleight A, Godel T, Martin J, Riemer C, Stadler H. 5-HT(6) receptor antagonists: lead optimisation and biological evaluation of N-aryl and N-heteroaryl 4-amino-benzene sulfonamides. Eur J Med Chem. 2001;36:165-78 pubmed
    ..Compounds with a logD profile indicative of brain penetration have been subjected to in vivo testing for reversal of a scopolamine-induced retention deficit in a passive avoidance paradigm. ..
  46. Bekaii Saab T, Mortazavi A, Hicks L, Zalupski M, Pelley R, Chan K, et al. A phase II study of chloroquinoxaline sulfonamide (CQS) in patients with metastatic colorectal carcinoma (MCRC). Invest New Drugs. 2006;24:343-6 pubmed
    ..No patients discontinued the treatment because of toxicity. CQS, when given at a dose of 2000 mg/m2 weekly for 4 weeks every 42 days to patients with metastatic colorectal cancer, does not result in significant tumor regression. ..
  47. Gitz D, Eells J, Pennock D. The dcc mutation affects ciliary length in Tetrahymena thermophila. J Eukaryot Microbiol. 1993;40:668-76 pubmed
    ..The mutation was named dcc for defective in ciliogenesis and cytokinesis. ..
  48. Sharaby C. Synthesis, spectroscopic, thermal and antimicrobial studies of some novel metal complexes of Schiff base derived from [N1-(4-methoxy-1,2,5-thiadiazol-3-yl)sulfanilamide] and 2-thiophene carboxaldehyde. Spectrochim Acta A Mol Biomol Spectrosc. 2007;66:1271-8 pubmed
    ..The antimicrobial activity of the obtained products was performed using Chloramphenicol and Grisofluvine as standards, indicate that in some cases metallation increase activity than the ligand. ..
  49. Suenaga S, Abeyama K, Hamasaki A, Mimura T, Noikura T. Temporomandibular disorders: relationship between joint pain and effusion and nitric oxide concentration in the joint fluid. Dentomaxillofac Radiol. 2001;30:214-8 pubmed
    ..05). Painful joints are more likely to demonstrate contrast enhancement of joint effusion. Nitric oxide concentration in TMJ fluid is closely associated with inflammatory changes and painful TM joints. ..
  50. Haritova A, Stanilova S. Enhanced expression of IL-10 in contrast to IL-12B mRNA in poultry with experimental coccidiosis. Exp Parasitol. 2012;132:378-82 pubmed publisher
    ..Sulfonamide treatment resulted in clinical improvement and restoration of IL-10 mRNA to the levels observed in healthy chickens. ..
  51. Branda R, Moore A, McCormack J. Immunosuppressive properties of chloroquinoxaline sulfonamide. Biochem Pharmacol. 1989;38:3521-6 pubmed
    ..These studies indicate that CQS inhibits essential basic processes in human lymphocytes. This agent may find use as an immunosuppressive drug. ..
  52. Teo C, Oh V, Kueh Y. Agranulocytosis and anaemia induced by sulfametopyrazine in a sulfametopyrazine-trimethoprim combination. Ann Acad Med Singapore. 1989;18:307-10 pubmed
    ..The case highlights the risk of severe haematological adverse reactions associated with sulphonamide treatment, and argues for the use of trimethoprim alone for uncomplicated cystitis. ..
  53. Long A, Short C, Barker S. Method for the isolation and liquid chromatographic determination of eight sulfonamides in milk. J Chromatogr. 1990;502:87-94 pubmed
    ..25 ng on column (62.5 ng/ml, 20 microliters injection from a final sample volume of 0.5 ml). Savings in terms of time and solvent make this procedure attractive when compared to classical isolation techniques for sulfonamides. ..