Sulfonamides interactions

Sugita O, Sawada Y, Sugiyama Y, Iga T, Hanano M. 1982. Physiologically based pharmacokinetics of drug-drug interaction a study of tolbutamide-sulfonamide interaction in rats. J Pharmacokinet Biopharm 10 297-316. 

Mendiratta, S. and Madan, A.K. (1994). Structure-Activity Study on Antiviral 5-Vinylpyrimidine Nucleoside Analogs Using Wiener s Topological Index. J.Chem.Inf.Comput.ScL, 34,867-871. Menziani, M.C. and De Benedetti, P.G. (1992). Molecular Mechanics and Quantum Chemical QSAR Analysis in Carbonic Anhydrase Heterocyclic Sulfonamide Interactions. Struct. CherrL,... 

Menziani, M.C. and De Benedetti, P.G. (1992) Molecular mechanics and quantum chemical QSAR analysis in carbonic anhydrase heterocyclic sulfonamide interactions. Struct. Chem., 3,215-219. 

The selective reaction of anionic 3,6-dichloro-4-sulfanilamidopy-ridazine with excess methanolic methoxide at the 3-position is another indication of the absence of major steric effects in most nucleophilic substitutions, as a result of the direction of nucleophilic attack (cf. Section II, A, 1). The selectivity at the 3-position is an example of the interaction of substituent effects. The sulfonamide anion deactivates both the 3-chloro (ortho direct deactivation) and... 

Discuss the uses, general drug actions, and general adverse reactions, contraindications, precautions, and interactions of the sulfonamides. 

Phenytoin interacts widi many different drugp. For example isoniazid, chloramphenicol, sulfonamides, benzodiazepines, succinimides, and cimetidine all increase phenytoin blood levels. The barbiturates, rifampin, theophylline, and warfarin decrease phenytoin blood levels. When administering the hydantoins with meperidine, die analgesic effect of meperidine is decreased. 

The antibiotic and sulfonamide ophthalmics are contraindicated in patients with a hypersensitivity to the drug or any component of the drug. These dru are also contraindicated in patients with epithelial herpes simplex keratitis, varicella, mycobacterial infection of the eye, and fungal diseases of the eye There are no significant precautions or interactions when the dru are administered as directed by the primary health care provider. 

Polytopic macrocyclic receptors 1, 2 (Figure 10.1) are able to complex the zwitterionic form of the amino acids by a double non-covalent charge interaction [28,29]. The unsymmetrical benzocrown sulfonamide derivative, 2 which contains benzo-18-crown-6 and benzo-15-crown-5 moieties was used as a ditopic receptor for multiple molecular recognition of the amino acids, by combining two non-covalent interactions ammonium-crown hydrogen bonding and carboxylate- complexed Na+-benzo-15-crown-5 charge interactions [28,33]. 

A different pH-triggered deshielding concept with hydrophilic polymers is based on reversing noncovalent electrostatic bonds [78, 195, 197]. For example, a pH-responsive sulfonamide/PEl system was developed for tumor-specific pDNA delivery [195]. At pH 7.4, the pH-sensitive diblock copolymer, poly(methacryloyl sulfadimethoxine) (PSD)-hZocA -PEG (PSD-b-PEG), binds to DNA/PEI polyplexes and shields against cell interaction. At pH 6.6 (such as in a hypoxic extracellular tumor environment or in endosomes), PSD-b-PEG becomes uncharged due to sulfonamide protonation and detaches from the nanoparticles, permitting PEI to interact with cells. In this fashion PSD-b-PEG is able to discern the small difference in pH between normal and tumor tissues. 

Sun, J. MacFarlane, D. R. Forsyth, M. A new family of ionic liquids based on the l-alkyl-2-methylpyrrolinium cation, Electrochim. Acta, 2003, 48(12), 1707-1711 Fors3dh, S. Golding, J. MacFarlane, D. R. Forsyth, M. A-methyl-iV-alkylpyrrolidinium tetrafluoroborate salts ionic solvents and solid electrolytes, Electrochim. Acta, 2001, 46(10-11), 1753-1757 Golding, J. J. Macfarlane, D. R. Spiccia, L. et al. Weak intermolecular interactions in sulfonamide salts structure of 1-ethyl-2-methyl-3-benzylimidazolium bis[(trifluoromethyl)sulfonyl]amide, Chem. Commun., 1998, 1593-1594. 

The plot in (b) refers to a similar interaction with the carboxymethylated derivative of carbonic anhydrase (Prob. 19). Aromatic sulfonamides are powerful inhibitors of the action of the enzyme and are useful probes of the site characteristics. 

Some possible interactions between a sulfonamide structural fragment and an active site. 

Fig. 5.5 Putative interactions of the cocrystallized selective Cox2 ligand SC-558 with its active site, assuming a neutral sulfonamide group - the state used to assign pharmacophore feature flags by the used software. Dotted lines stand for hydrogen bonds, the other residues being responsible for hydrophobic contacts. From a physicochemical point of view, an ionized SO2 NH involved in a salt bridge with Arg 513 and hydrogen bonding to the other tautomer of His 90 would make more sense.

Hydrazide 1 was designed as the CA anchor fragment and hence necessitated dual functionality an Ar-SO NH moiety for reliable CA affinity and a hydrazide moiety to take part in hydrazone exchange. Hydrazide 2 lacked the sulfonamide moiety of 1, but was still able to participate in hydrazone exchange and thus functioned as a control compound. Fragments A-E, the exchange partners for 1 and 2, were selected to introduce an array of tails onto 1 to enable exploration of periphery recognition interactions with CA. 

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