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Molecular Pharmaceutics Oct 2015Understanding the polymorphism exhibited by organic active-pharmaceutical ingredients (APIs), in particular the relationships between crystal structure and the...
Understanding the polymorphism exhibited by organic active-pharmaceutical ingredients (APIs), in particular the relationships between crystal structure and the thermodynamics of polymorph stability, is vital for the production of more stable drugs and better therapeutics, and for the economics of the pharmaceutical industry in general. In this article, we report a detailed study of the structure-property relationships among the polymorphs of the model API, Sulfamerazine. Detailed experimental characterization using synchrotron radiation is complemented by computational modeling of the lattice dynamics and mechanical properties, in order to study the origin of differences in millability and to investigate the thermodynamics of the phase equilibria. Good agreement is observed between the simulated phonon spectra and mid-infrared and Raman spectra. The presence of slip planes, which are found to give rise to low-frequency lattice vibrations, explains the higher millability of Form I compared to Form II. Energy/volume curves for the three polymorphs, together with the temperature dependence of the thermodynamic free energy computed from the phonon frequencies, explains why Form II converts to Form I at high temperature, whereas Form III is a rare polymorph that is difficult to isolate. The combined experimental and theoretical approach employed here should be generally applicable to the study of other systems that exhibit polymorphism.
Topics: Crystallization; Crystallography, X-Ray; Molecular Structure; Sulfamerazine; Synchrotrons; Thermodynamics
PubMed: 26317333
DOI: 10.1021/acs.molpharmaceut.5b00504 -
Archiv Der Pharmazie Jan 2021A novel series of sulfonamides, 4-(3-phenyltriaz-1-en-1-yl)-N-(4-methyl-2-pyrimidinyl)benzenesulfonamides (1-9), was designed and synthesized by the diazo reaction...
A novel series of sulfonamides, 4-(3-phenyltriaz-1-en-1-yl)-N-(4-methyl-2-pyrimidinyl)benzenesulfonamides (1-9), was designed and synthesized by the diazo reaction between sulfamerazine and substituted aromatic amines for the first time. Their chemical structures were characterized by H nuclear magnetic resonance (NMR), C NMR, and high-resolution mass spectra. The newly synthesized compounds were evaluated in terms of acetylcholineasterase (AChE) and human carbonic anhydrases (hCA) I and II isoenzymes inhibitory activities. According to the AChE inhibition results, the K values of the compounds 1-9 were in the range of 19.9 ± 1.5 to 96.5 ± 20.7 nM against AChE. Tacrine was used as the reference drug and its K value was 49.2 ± 2.7 nM against AChE. The K values of the compounds 1-9 were in the range of 10.2 ± 2.6 to 101.4 ± 27.8 nM against hCA I, whereas they were 18.3 ± 4.4 to 48.1 ± 4.5 nM against hCA II. Acetazolamide was used as a reference drug and its K values were 72.2 ± 5.4 and 52.2 ± 5.7 nM against hCA I and hCA II, respectively. The most active compounds, 1 (nonsubstituted) against AChE, 5 (4-ethoxy-substituted) against hCA I, and 8 (4-bromo-substituted) against hCA II, were chosen and docked at the binding sites of these enzymes to explain the inhibitory activities of the series. The newly synthesized compounds presented satisfactory pharmacokinetic properties via the estimation of ADME properties.
Topics: Acetylcholinesterase; Carbonic Anhydrase I; Carbonic Anhydrase II; Carbonic Anhydrase Inhibitors; Cholinesterase Inhibitors; Computer Simulation; Humans; Structure-Activity Relationship; Sulfamerazine; Triazenes
PubMed: 32984993
DOI: 10.1002/ardp.202000243 -
International Journal of Pharmaceutics May 2016A comprehensive study on the dissolution properties of three co-amorphous sulfamerazine/excipient systems, namely sulfamerazine/deoxycholic acid, sulfamerazine/citric...
A comprehensive study on the dissolution properties of three co-amorphous sulfamerazine/excipient systems, namely sulfamerazine/deoxycholic acid, sulfamerazine/citric acid and sulfamerazine/sodium taurocholate (SMZ/DA, SMZ/CA and SMZ/NaTC; 1:1 molar ratio), is reported. While all three co-formers stabilize the amorphous state during storage, only co-amorphization with NaTC provides a dissolution advantage over crystalline SMZ and the reasons for this were analyzed. In the case of SMZ/DA extensive gelation of DA protects the amorphous phase from crystallization upon contact with buffer, but at the same time prevents the release of SMZ into solution. Disk dissolution studies showed an improved dissolution behavior of SMZ/CA compared to crystalline SMZ. However, enhanced dissolution properties were not seen in powder dissolution testing due to poor dispersibility. Co-amorphization of SMZ and NaTC resulted in a significant increase in dissolution rate, both in powder and disk dissolution studies.
Topics: Anti-Bacterial Agents; Chemistry, Pharmaceutical; Citric Acid; Crystallization; Deoxycholic Acid; Excipients; Solubility; Sulfamerazine; Taurocholic Acid
PubMed: 26992818
DOI: 10.1016/j.ijpharm.2016.03.023 -
Journal of Pharmaceutical and... Sep 2023This study aimed to develop a molecularly imprinted polymer (MIP) sensor using electropolymerization of thiophene acetic acid monomer around template molecules,...
ZnO and Au nanoparticles supported highly sensitive and selective electrochemical sensor based on molecularly imprinted polymer for sulfaguanidine and sulfamerazine detection.
This study aimed to develop a molecularly imprinted polymer (MIP) sensor using electropolymerization of thiophene acetic acid monomer around template molecules, sulfaguanidine (SGN) and sulfamerazine (SMR), for selective and sensitive detection of both antibiotics. Au nanoparticles were then deposited on the modified electrode surface, and SGN and SMR were extracted from the resulting layer. Surface characterization, changes in the oxidation peak current of both analytes, and investigation of the electrochemical properties of the MIP sensor were examined using scanning electron microscopy, cyclic voltammetry, and differential pulse voltammetry. The developed MIP sensor with Au nanoparticles showed a detection limit of 0.030 µmol L and 0.046 µmol L for SGN and SMR, respectively, with excellent selectivity in the presence of interferents. The sensor was successfully used for SGN and SMR analysis in human fluids, including blood serum and urine, with excellent stability and reproducibility.
Topics: Humans; Molecularly Imprinted Polymers; Sulfamerazine; Sulfaguanidine; Gold; Zinc Oxide; Metal Nanoparticles; Reproducibility of Results; Molecular Imprinting; Electrochemical Techniques; Electrodes; Limit of Detection
PubMed: 37336038
DOI: 10.1016/j.jpba.2023.115518 -
Journal of Hazardous Materials Jan 2021The dynamics of oxytetracycline (OTC), sulfamerazine (SM1), ciprofloxacin (CIP) and related antibiotic resistance genes (ARGs) during swine manure composting were...
The dynamics of oxytetracycline (OTC), sulfamerazine (SM1), ciprofloxacin (CIP) and related antibiotic resistance genes (ARGs) during swine manure composting were compared between manure collected from swine fed a diet containing these three antibiotics (T) and manure directly spiked with these drugs (T). The composting removal efficiency of OTC (94.9 %) and CIP (87.8 %) in the T treatment was significantly higher than that of OTC (83.8 %, P < 0.01) and CIP (83.9 %, P < 0.05) in the T treatment, while SM1 exhibited no significant difference (P > 0.05) between the two treatments. Composting effectively reduced the majority of ARGs in both T and T types of manure, especially tetracycline resistance genes (TRGs). Compared with the T treatment, the abundance of some ARGs, such as tetG, qepA, sul1 and sul2, increased dramatically up to 309-fold in the T treatment. The microbial composition of the composting system changed significantly during composting due to antibiotic feeding. Redundancy analysis suggested that the abundance of ARGs had a considerable impact on alterations in the physicochemical parameters (C/N, pH and temperature) and bacterial communities (Actinobacteria, Proteobacteria and Firmicutes) during the composting of swine manure.
Topics: Animals; Anti-Bacterial Agents; Ciprofloxacin; Composting; Drug Resistance, Microbial; Genes, Bacterial; Manure; Oxytetracycline; Sulfamerazine; Swine
PubMed: 33254754
DOI: 10.1016/j.jhazmat.2020.123710 -
Bioresource Technology Sep 2018Pollution of water by single antibiotics has been investigated in depth. However, in reality, a wide range of different contaminants is often mixed in the aquatic...
Pollution of water by single antibiotics has been investigated in depth. However, in reality, a wide range of different contaminants is often mixed in the aquatic environment (contaminant cocktail). Here, single and competitive sorption dynamics of ionizable norfloxacin (NOR), sulfamerazine (SMR) and oxytetracycline (OTC) by both pristine and modified biochars were investigated. Sorption kinetics of the three antibiotics was faster in ternary-solute than single-solute system. Sorption efficiency was enhanced in the competitive system for NOR by the pristine biochar, and for OTC by both the pristine biochar and the modified biochar, while SMR sorption by the pristine biochar and the KOH-modified biochar was inhibited. Sorption was governed by electrostatic interactions, π-π EDA and H-bonds for antibiotics sorption by biochar. SMR and OTC sorption by biochar was influenced by cation bridging and surface complexation, respectively. This research finding will guide the development of treatment procedures for water polluted by multiple antibiotics.
Topics: Adsorption; Charcoal; Norfloxacin; Oxytetracycline; Sulfamerazine; Water Purification
PubMed: 29763802
DOI: 10.1016/j.biortech.2018.05.022 -
Life Sciences May 1986The ability of rat hepatic uroporphyrinogen cosynthase to direct formation of uroporphyrinogen III and the synthesis of uroporphyrinogen in vitro was impaired by...
The ability of rat hepatic uroporphyrinogen cosynthase to direct formation of uroporphyrinogen III and the synthesis of uroporphyrinogen in vitro was impaired by sulfamerazine. Inhibition was reversed by the addition of folic acid. Administration of a single, oral dose (1 g/kg) of sulfamerazine to rats was associated with elevated levels of hepatic uroporphyrin I isomer. These results suggest that sulfonamides may interfere with the biosynthesis of uroporphyrinogen III.
Topics: Ammonia-Lyases; Animals; Folic Acid; Hydro-Lyases; Hydroxymethylbilane Synthase; Isomerism; Kinetics; Liver; Male; Porphyrinogens; Rats; Rats, Inbred Strains; Sulfamerazine; Uroporphyrinogen III Synthetase; Uroporphyrinogens
PubMed: 3702597
DOI: 10.1016/0024-3205(86)90412-1 -
Journal of the American Veterinary... Jul 1946
Topics: Animals; Sulfamerazine; Veterinary Medicine
PubMed: 20988131
DOI: No ID Found -
Journal of Colloid and Interface Science Oct 2022In the photo-Fenton reactions, fast recombination of photoinduced electrons and holes in Fe-based metal-organic frameworks (Fe-MOFs) slows Fe(III)/Fe(II) cycle, which...
In the photo-Fenton reactions, fast recombination of photoinduced electrons and holes in Fe-based metal-organic frameworks (Fe-MOFs) slows Fe(III)/Fe(II) cycle, which remains big challenge that significantly retards the overall process. Herein, NH-MIL-88B(Fe) (NM88) was modified with 3,5-diaminobenzoic acid (DB) and TPB-DMTP-COF (COF-OMe) to in situ construct NM88(DB)/COF-OMe composite that could strongly harvest the visible light for photo-Fenton degradation of sulfamerazine (SMR). With the addition of DB, electron-donating effect of NM88 was strengthened, which then promoted amino groups to react with aldehyde groups (Schiff-base), and thus highly facilitated the interfacial contact between NM88 and COF-OMe. Such modifications increased the degradation rate constants for NM88(DB)/COF-OMe to 15.1 and 17.3 times that of NM88 and COF-OMe respectively with good reusability. Moreover, the catalyst exhibited 32-170 times higher degradation kinetics in comparison to other reported catalysts. Results showed that due to the Schiff-base reaction between NM88(DB) and COF-OMe, electron density on Fe(III) was decreased; and the photogenerated electrons of COF-OMe moved to NM88(DB) to reduce Fe(III), thus resulting in the generation of highly active Fe(II) and ·OH species. Furthermore, the main reactive species were determined to be ·OH and ·O by trapping experiments, and a possible mechanism of the degradation system followed Z-scheme charge transfer.
Topics: Electronics; Ferric Compounds; Ferrous Compounds; Sulfamerazine
PubMed: 35660881
DOI: 10.1016/j.jcis.2022.05.142 -
British Medical Journal Dec 1975
Review
Topics: Colon; Drug Combinations; Drug Therapy; Endocarditis, Bacterial; Gas Gangrene; Humans; Infant, Newborn; Infant, Newborn, Diseases; Intestinal Diseases; Neutropenia; Nitrofurantoin; Penicillin G; Penicillin G Benzathine; Penicillin G Procaine; Penicillin Resistance; Preanesthetic Medication; Preventive Medicine; Respiratory Tract Infections; Rheumatic Fever; Sulfadiazine; Sulfamerazine; Sulfathiazoles; Surgical Wound Infection; Urinary Tract Infections
PubMed: 1106812
DOI: 10.1136/bmj.4.5996.561