-
JAMA Dermatology Apr 2023Antibiotics are an important risk for Stevens-Johnson syndrome and toxic epidermal necrolysis (SJS/TEN), which are the most severe types of drug hypersensitivity... (Meta-Analysis)
Meta-Analysis
IMPORTANCE
Antibiotics are an important risk for Stevens-Johnson syndrome and toxic epidermal necrolysis (SJS/TEN), which are the most severe types of drug hypersensitivity reaction with a mortality rate up to 50%. To our knowledge, no global systematic review has described antibiotic-associated SJS/TEN.
OBJECTIVE
To evaluate the prevalence of antibiotics associated with SJS/TEN worldwide.
DATA SOURCES
The MEDLINE and Embase databases were searched for experimental and observational studies that described SJS/TEN risks since database inception to February 22, 2022.
STUDY SELECTION
Included studies adequately described SJS/TEN origins and specified the antibiotics associated with SJS/TEN.
DATA EXTRACTION AND SYNTHESIS
Two reviewers (E.Y.L. and C.K.) independently selected the studies, extracted the data, and assessed the risk of bias. A meta-analysis using a random-effects model was performed in the studies that described patient-level associations. Subgroup analyses were performed to explore the heterogeneity. The risk of bias was assessed using the Joanna Briggs Institute checklist, and the certainty of evidence was rated using the GRADE (Grading of Recommendations Assessment, Development and Evaluation) approach.
MAIN OUTCOMES AND MEASURES
Prevalence of antibiotic-associated SJS/TEN was presented as pooled proportions with 95% CIs.
RESULTS
Among the 64 studies included in the systematic review, there were 38 studies that described patient-level associations; the meta-analysis included these 38 studies with 2917 patients to determine the prevalence of single antibiotics associated with SJS/TEN. The pooled proportion of antibiotics associated with SJS/TEN was 28% (95% CI, 24%-33%), with moderate certainty of evidence. Among antibiotic-associated SJS/TEN, the sulfonamide class was associated with 32% (95% CI, 22%-44%) of cases, followed by penicillins (22%; 95% CI, 17%-28%), cephalosporins (11%; 95% CI, 6%-17%), fluoroquinolones (4%; 95% CI, 1%-7%), and macrolides (2%; 95% CI, 1%-5%). There was a statistically significant heterogeneity in the meta-analysis, which could be partially explained in the subgroup analysis by continents. The overall risk of bias was low using the Joanna Briggs Institute checklist for case series.
CONCLUSION AND RELEVANCE
In this systematic review and meta-analysis of all case series, antibiotics were associated with more than one-quarter of SJS/TEN cases described worldwide, and sulfonamide antibiotics remained the most important association. These findings highlight the importance of antibiotic stewardship, clinician education and awareness, and weighing the risk-benefit assessment of antibiotic choice and duration.
Topics: Humans; Stevens-Johnson Syndrome; Anti-Bacterial Agents; Prevalence; Sulfanilamide; Retrospective Studies
PubMed: 36790777
DOI: 10.1001/jamadermatol.2022.6378 -
Proceedings of the Royal Society of... Feb 1964
Topics: Anti-Bacterial Agents; Antibiotics, Antitubercular; Antifungal Agents; Bacteriological Techniques; Black People; Epidemiology; Humans; Mycetoma; Sulfanilamide; Sulfanilamides; Sulfonamides; West Indies; Wound Infection
PubMed: 14116020
DOI: No ID Found -
Molecules (Basel, Switzerland) Dec 2022Sulfonamides are the basic motifs for a whole generation of drugs from a large group of antibiotics. Currently, research in the field of the new sulfonamide synthesis... (Review)
Review
Sulfonamides are the basic motifs for a whole generation of drugs from a large group of antibiotics. Currently, research in the field of the new sulfonamide synthesis has received a "second wind", due to the increase in the synthetic capabilities of organic chemistry and the study of their medical and biological properties of a wide spectrum of biological activity. New reagents and new reactions make it possible to significantly increase the number of compounds with a sulfonamide fragment in combination with other important pharmacophore groups, such as, for example, a wide class of -containing heterocycles. The result of these synthetic possibilities is the extension of the activity spectrum-along with antibacterial activity, many of them exhibit other types of biological activity. Antiviral activity is also observed in a wide range of sulfonamide derivatives. This review provides examples of the synthesis of sulfonamide compounds with antiviral properties that can be used to develop drugs against coxsackievirus B, enteroviruses, encephalomyocarditis viruses, adenoviruses, human parainfluenza viruses, Ebola virus, Marburg virus, SARS-CoV-2, HIV and others. Since over the past three years, viral infections have become a special problem for public health throughout the world, the development of new broad-spectrum antiviral drugs is an extremely important task for synthetic organic and medicinal chemistry. Sulfonamides can be both sources of nitrogen for building a nitrogen-containing heterocyclic core and the side chain substituents of a biologically active substance. The formation of the sulfonamide group is often achieved by the reaction of the -nucleophilic center in the substrate molecule with the corresponding sulfonylchloride. Another approach involves the use of sulfonamides as the reagents for building a nitrogen-containing framework.
Topics: Humans; Antiviral Agents; Sulfonamides; COVID-19; SARS-CoV-2; Sulfanilamide; Anti-Bacterial Agents; Indicators and Reagents; Nitrogen
PubMed: 36615245
DOI: 10.3390/molecules28010051 -
The Indian Medical Gazette Feb 1947
Topics: Sulfanilamide; Sulfanilamides; Sulfonamides
PubMed: 20242781
DOI: No ID Found -
The Indian Medical Gazette Mar 1947
Topics: Sulfanilamide; Sulfanilamides; Sulfonamides
PubMed: 20343545
DOI: No ID Found -
The Indian Medical Gazette Jan 1947
Topics: Crime; Criminal Psychology; Criminals; Humans; Prisoners; Sulfanilamide; Sulfanilamides; Sulfonamides
PubMed: 20241028
DOI: No ID Found -
British Medical Journal May 1964
Topics: Bacteriology; History, 19th Century; History, 20th Century; Sulfanilamide; Sulfanilamides; Sulfonamides
PubMed: 14120818
DOI: No ID Found -
Molecules (Basel, Switzerland) Apr 2023The development of heterocyclic derivatives has progressed considerably over the past decades, and many new carbonic anhydrase inhibitors (CAIs) fall into this field. In... (Review)
Review
The development of heterocyclic derivatives has progressed considerably over the past decades, and many new carbonic anhydrase inhibitors (CAIs) fall into this field. In particular, five-membered heterocyclic sulfonamides have been generally shown to be more effective inhibitors compared to six-membered rings ones. Despite the importance of oxygen and nitrogen five-membered heterocyclic aromatic rings in medicinal chemistry, the installation of sulfonamide moiety on such heterocycles has not received much attention. On the other hand, 1,3,4-thiadiazole/thiadiazoline ring-bearing sulfonamides are the scaffolds which have been widely used in a variety of pharmaceutically important CAIs such as acetazolamide, metazolamide and their many derivatives obtained by using the tail approach. Here, we reviewed the field focusing on the diverse biological activities of these CAIs, such as antiglaucoma, antiepileptic, antitumor and antiinfective properties. This review highlights developments involving five-membered heterocyclic sulfonamides over the last years, with a focus on their pharmacological/clinical applications.
Topics: Carbonic Anhydrase Inhibitors; Sulfonamides; Structure-Activity Relationship; Acetazolamide; Anticonvulsants; Sulfanilamide; Dermatologic Agents
PubMed: 37049983
DOI: 10.3390/molecules28073220 -
Acta Crystallographica. Section C,... Dec 2022In the search for new `sulfa drugs' with therapeutic properties, o-nitrosulfonamides and N-cycloamino-o-sulfanilamides were synthesized and characterized using...
N-Cycloamino substituent effects on the packing architecture of ortho-sulfanilamide molecular crystals and their in silico carbonic anhydrase II and IX inhibitory activities.
In the search for new `sulfa drugs' with therapeutic properties, o-nitrosulfonamides and N-cycloamino-o-sulfanilamides were synthesized and characterized using techniques including H NMR, C NMR and FT-IR spectroscopy, and single-crystal X-ray diffraction (SC-XRD). The calculated density functional theory (DFT)-optimized geometry of the molecules showed similar conformations to those obtained by SC-XRD. Molecular docking of N-piperidinyl-o-sulfanilamide and N-indolinyl-o-sulfanilamide supports the notion that o-sulfanilamides are able to bind to human carbonic anhydrase II and IX inhibitors (hCA II and IX; PDB entries 4iwz and 5fl4). Hirshfeld surface analyses and DFT studies of three o-nitrosulfonamides {1-[(2-nitrophenyl)sulfonyl]pyrrolidine, CHNOS, 1, 1-[(2-nitrophenyl)sulfonyl]piperidine, CHNOS, 2, and 1-[(2-nitrophenyl)sulfonyl]-2,3-dihydro-1H-indole, CHNOS, 3} and three N-cycloamino-o-sulfanilamides [2-(pyrrolidine-1-sulfonyl)aniline, CHNOS, 4, 2-(piperidine-1-sulfonyl)aniline, CHNOS, 5, and 2-(2,3-dihydro-1H-indole-1-sulfonyl)aniline, CHNOS, 6] suggested that forces such as hydrogen bonding and π-π interactions hold molecules together and further showed that charge transfer could promote bioactivity and the ability to form biological interactions at the piperidinyl and phenyl moieties.
Topics: Humans; Sulfanilamide; Carbonic Anhydrase II; Molecular Docking Simulation; Spectroscopy, Fourier Transform Infrared; Crystallography, X-Ray; Hydrogen Bonding; Aniline Compounds; Piperidines; Pyrrolidines
PubMed: 36468556
DOI: 10.1107/S2053229622010130 -
Molecules (Basel, Switzerland) Nov 2022The occurrence and distribution of antibiotics in the environment has received increasing attention due to their potential adverse effects on human health and... (Meta-Analysis)
Meta-Analysis Review
The occurrence and distribution of antibiotics in the environment has received increasing attention due to their potential adverse effects on human health and ecosystems. Humic substances (HS) influence the mobility, reactivity, and bioavailability of antibiotics in the environment significantly due to their interaction. As a result, HS can affect the dissemination of antibiotic-resistance genes, which is one of the main problems arising from contamination with antibiotics. The review provides quantitative data on the binding of HS with fluoroquinolones, macrolides, sulfonamides, and tetracyclines and reports the proposed mechanisms of their interaction. The main issues of the quantification of antibiotic-HS interaction are discussed, which are a development of standard approaches and the accumulation of a dataset using a standard methodology. This would allow the implementation of a meta-analysis of data to reveal the patterns of the binding of antibiotics to HS. Examples of successful development of humic-based sorbents for fluoroquinolone and tetracycline removal from environmental water systems or polluted wastewaters were given. Data on the various effects of HS on the dissemination of antibiotic-resistance genes (ARGs) were summarized. The detailed characterization of HS properties as a key point of assessing the environmental consequences of the formation of antibiotic-HS complexes, such as the dissemination of antibiotic resistance, was proposed.
Topics: Humans; Anti-Bacterial Agents; Humic Substances; Ecosystem; Fluoroquinolones; Sulfanilamide
PubMed: 36431855
DOI: 10.3390/molecules27227754