Sulfonamide Hypersensitivity

Chow, Timothy; Khan, David A.

doi:10.1007/s12016-021-08872-3

Cited by 16 publications

(13 citation statements)

References 99 publications

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“…The rash is classically divided into 2 phases: an acute phase of pruritic violaceous patches and plaques with central duskiness, followed by a residual phase of hyperpigmentation that can last several months. The sulfonamide moiety of TMP‐SMX is a common cause of FDE 3 …”

Section: Diagnosismentioning

confidence: 99%

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Man with recurrent rash

Clos

Mittelman

2023

JACEP Open

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Patient presentationA 33-year-old male presented to the emergency department with a diffuse pruritic rash that appeared several days after starting trimethoprim/sulfamethoxazole (TMP-SMX) for a dental infection. Initially beginning on the torso and low back, the rash spread to the palms, soles, and genitalia. Lesions were described as violaceous, non-blanching patches with a dusky center (Figures 1-3). Progression stopped after discontinuing TMP-SMX. He conveyed a remote history of a similar rash following use of an unknown medication.

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Section: Diagnosismentioning

confidence: 99%

“…The sulfonamide moiety of TMP-SMX is a common cause of FDE. 3 Management of FDE anchors on identification and discontinuation of the causative agent. The majority of cases involve 5 or fewer lesions; however, generalized or bullous cases (>10% total body surface area,…”

Section: Fixed Drug Eruptionmentioning

confidence: 99%

Man with recurrent rash

Clos

Mittelman

2023

JACEP Open

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“…Those drugs have shown poor specificity for the targeted isozyme, therefore causing a wide range of undesirable side effects, including altered taste, malaise, fatigue, depression, and anorexia [ 25 , 26 ]. In addition, some of the marketed sulfonamide drugs cause allergies in a significant number of people [ 27 , 28 ]. Thus, the discovery of a new class of non-sulfonamide CA inhibitors, potentially with more controlled specificity for different CA isozymes, could lead to the development of useful alternatives to existing drugs.…”

Section: Introductionmentioning

confidence: 99%

“…Imidazole-containing drugs have a broader scope in remedying various dispositions in clinical medicine [ 26 ]. Similarly, pyrimidine is also a heterocyclic compound that has shown diverse biological activities, such as antimicrobial, CNS-depressant, anti-inflammatory, analgesic, anti-convulsant, anticancer, anti-helmentic, antioxidant, and herbicidal [ 27 ]. The pyrazole-based imidazole derivatives are reported as potent inhibitors of hCA-IX and hCA-II [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis with Green Chemistry Approach of Novel Pharmacophores of Imidazole-Based Hybrids for Tumor Treatment: Mechanistic Insights from In Situ to In Silico

Khan

Shah

Khan

et al. 2022

Cancers

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Imidazole-based pyrimidine hybrids are considered a remarkable class of compounds in pharmaceutical chemistry. Here, we report the anticancer bioactivities of eleven imidazole-based pyrimidine hybrids (1–11) that specifically target cytosolic carbonic anhydrase (CAs) isoenzymes, including human CA-II and human CA-IX (hCA-II, and hCA-IX). A highly eco-friendly aqueous approach was used for the formation of a carbon–carbon bond by reacting aromatic nitro group substitution of nitroimidazoles with carbon nucleophiles. The in vitro results indicate that this new class of compounds (1–11) includes significant inhibitors of hCA IX with IC50 values in the range of 9.6 ± 0.2–32.2 ± 1.0 µM, while hCA II showed IC50 values in range of 11.6 ± 0.2–31.1 ± 1.3 µM. Compound 2 (IC50 = 12.3 ± 0.1 µM) showed selective inhibition for hCA-II while 7, 8, and 10 (IC50 = 9.6–32.2 µM) were selective for hCA-IX. The mechanism of action was investigated through in vitro kinetics studies that revealed that compounds 7, 3, 11, 10, 4, and 9 for CA-IX and 1, 2, and 11 for CA-II are competitive inhibitors with dissociation constant (Ki) in the range of 7.32–17.02 µM. Furthermore, the in situ cytotoxicity of these compounds was investigated in the human breast cancer cell line MDA-MB-231 and compared with the normal human breast cell line, MCF-10A. Compound 5 showed excellent anticancer/cytotoxic activity in MDA-MB-231 with no toxicity to the normal breast cells. In addition, in silico molecular docking was employed to predict the binding mechanism of active compounds with their targets. This in silico observation aligned with our experimental results. Our findings signify that imidazole-based hybrids could be a useful choice to design anticancer agents for breast and lung tumors, or antiglaucoma compounds, by specific inhibition of carbonic anhydrases.

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“…5 Cutaneous delayed reactions to sulfonamides occur within 3–13 days of initiation and are dose-dependent. 5…”

mentioning

confidence: 99%