Dapsone-induced Hemolytic Anemia in Lung Allograft Recipients

Naik, P.M.; Lyon, G. Marshall; Ramirez, Allan; Lawrence, E. Clinton; Neujahr, David C.; Force, Seth D.; Peláez, Andrés

doi:10.1016/j.healun.2008.07.025

Cited by 31 publications

(38 citation statements)

References 15 publications

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“…The experimental information in Table 4 for Dapsone was taken from ref. [17]. Note, that the agreement in measured and calculated wavenumbers cannot be too good, because the molecules in the calculations are in the gas phase, while the experimental spectra were recorded in condensed phase leading to intermolecular interactions not present in the calculated models.…”

Section: Discussionmentioning

confidence: 93%

“…We extended the work to diphenylsulfone [18,19] as the main building unit of the sulfa drug to understand the nature of the forces that control the conformational stability of such an important system. In an early study the characteristic vibrational modes of the -NH 2 and SO 2 groups and the aromatic ring have been assigned from isotopic shifts and studies in different solvents [17]. The determination of the molecular structure of Dapsone has shown that in the solid state it has a structure that slightly deviates from C 2v symmetry, with the benzene rings almost parallel to each other and both nearly perpendicular to the OSO plane [8] (see Table 2 for a definition of these geometries).…”

Section: Discussionmentioning

confidence: 99%

“…Calculated (dp denotes calculated depolarization ratio) and observed wavenumbers (Infrared and Raman spectra) [17] together with the ratio of observed to calculated wavenumbers (always with the observed infrared wavenumbers if possible) and the assignment of the vibrations to atomic motions based on the program GAUSSVIEW for 4,4 -sulfonyldianiline (Dapsone, C 2v : 23 the vibrational frequencies of the ground state structures at the DFT-B3LYP/6-311G** level of calculation, since it is well known that DFT yields wavenumbers in rather good agreement with experiment. Assignments of the normal modes were carried out using the program GAUSSVIEW 3.0 for the stable conformers of the molecules instead of normal mode calculations as described previously [10,11,23].…”

Section: Vibrational Wavenumbers Spectra and Assignments Of Normal Mmentioning

confidence: 99%

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A DFT Analysis of the Molecular Structures and Vibrational Spectra of Diphenylsulfone and 4,4'-Sulfonyldianiline (Dapsone)

Förner

Badawi

2011

Zeitschrift Für Naturforschung B

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We have performed density functional calculations with the B3LYP functional and a 6-311G** basis set to obtain the vibrational spectra in harmonic approximation of the anti-leprosy drug Dapsone and the parent compound diphenylsulfone. Although the chemical difference between the two molecules is not that pronounced (Dapsone has amino groups in the para positions in the phenyl rings), Dapsone is an active drug, while to our knowledge diphenylsulfone shows no medical activity. We compared the theoretical results to experimental vibrational spectra found in the literature. With the help of the program GAUSSVIEW we were able to assign the experimentally found spectral lines to specific atomic motions. The remarkable difference between the two molecules, regarding their structural behavior, is that the drug Dapsone has a more flexible structure of the phenyl ring than the parent molecule has. This might contribute to a greater ability of the drug to fit into receptor sites in a cell membrane although one has to be well aware that this plays most propably only a minor role in the drug activity of Dapsone.

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Section: Discussionmentioning

confidence: 93%

Section: Discussionmentioning

confidence: 99%

Section: Vibrational Wavenumbers Spectra and Assignments Of Normal Mmentioning

confidence: 99%

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A DFT Analysis of the Molecular Structures and Vibrational Spectra of Diphenylsulfone and 4,4'-Sulfonyldianiline (Dapsone)

Förner

Badawi

2011

Zeitschrift Für Naturforschung B

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“…Clinical risk factors associated with methemoglobinemia include renal failure (13), sepsis, gastrointestinal infection (14) and decreased glucose-6-phosphatase dehydrogenase (G6PD) activity (15). G6PD is necessary to generate NADPH, which otherwise maintains an adequate glutathione concentration within erythrocytes and counteracts hemoglobin oxidation.…”

Section: Discussionmentioning

confidence: 99%

Methemoglobinemia Induced by Trimethoprim-Sulfamethoxazole in a Patient with Systemic Lupus Erythematosus

et al. 2013

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We herein report a case of methemoglobinemia induced by trimethoprim-sulfamethoxazole (TMP/SMX). A 41-year-old woman with systemic lupus erythematosus (SLE) received TMP/SMX for prophylaxis of pneumocystis pneumonia (PCP) on the 7th day of hospitalization. She suddenly developed dyspnea and cyanosis on the 9th day of hospitalization. The level of oxygen saturation (SaO2) decreased, and the concentration of methemoglobin (MetHb) in the blood was elevated. We diagnosed the patient with methemoglobinemia induced by TMP/SMX. Methemoglobinemia should be considered in cases of sudden dyspnea following TMP/ SMX administration.

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“…Prophylactic antimicrobial agents, including ganciclovir, valganciclovir, dapsone, and trimethoprim-sulfamethoxazole, can cause myelosuppression and anemia. Glucose 6-phosphate dehydrogenase is an essential enzyme for normal RBC life span and oxidizing processes, and in its absence, dapsone and, less commonly, trimethoprim-sulfamethoxazole, can lead to sudden destruction of RBCs and hemolytic anemia (16,34). Ganciclovir and valganciclovir induce bone marrow suppression in 8% to 25% of solid-organ transplant patients (35).…”

Section: Medicationsmentioning

confidence: 99%