Fixed drug eruption caused by noscapine

Ishiguro, Emiko; Hatamochi, Atsushi; Hayashi, Shujiro; Hamasaki, Yoichiro; Yamazaki, Soji

doi:10.1111/j.1346-8138.2010.01118.x

Cited by 3 publications

(2 citation statements)

References 5 publications

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“…From new literature, it is known that the Netherlands Pharmacovigilance Centre received 10 reports of angioedema associated with the use of noscapine between 1987 and 2013 . Furthermore, two cases of erythema occurring in Japan after noscapine administration have been published (Ishiguro et al., ).…”

Section: Assessmentmentioning

confidence: 99%

Update of the Scientific Opinion on opium alkaloids in poppy seeds

Knutsen¹,

Alexander²,

Barregård³

et al. 2018

EFS2

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Poppy seeds are obtained from the opium poppy (Papaver somniferum L.). They are used as food and to produce edible oil. The opium poppy plant contains narcotic alkaloids such as morphine and codeine. Poppy seeds do not contain the opium alkaloids, but can become contaminated with alkaloids as a result of pest damage and during harvesting. The European Commission asked EFSA to provide an update of the Scientific Opinion on opium alkaloids in poppy seeds. The assessment is based on data on morphine, codeine, thebaine, oripavine, noscapine and papaverine in poppy seed samples. The CONTAM Panel confirms the acute reference dose (ARfD) of 10 lg morphine/kg body weight (bw) and concluded that the concentration of codeine in the poppy seed samples should be taken into account by converting codeine to morphine equivalents, using a factor of 0.2. The ARfD is therefore a group ARfD for morphine and codeine, expressed in morphine equivalents. Mean and high levels of dietary exposure to morphine equivalents from poppy seeds considered to have high levels of opium alkaloids (i.e. poppy seeds from varieties primarily grown for pharmaceutical use) exceed the ARfD in most age groups. For poppy seeds considered to have relatively low concentrations of opium alkaloids (i.e. primarily varieties for food use), some exceedance of the ARfD is also seen at high levels of dietary exposure in most surveys. For noscapine and papaverine, the available data do not allow making a hazard characterisation. However, comparison of the dietary exposure to the recommended therapeutical doses does not suggest a health concern for these alkaloids. For thebaine and oripavine, no risk characterisation was done due to insufficient data. However, for thebaine, limited evidence indicates a higher acute lethality than for morphine and the estimated exposure could present a health risk.

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Section: Assessmentmentioning

confidence: 99%

Update of the Scientific Opinion on opium alkaloids in poppy seeds

Knutsen¹,

Alexander²,

Barregård³

et al. 2018

EFS2

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“…Unlike taxanes and vincas, it is water soluble and readily crosses the blood–brain barrier. However, it exhibits some toxic effects such as fixed drug eruption (20). It has also been demonstrated to slow down the growth rate of dorsal root ganglion cultures by affecting axonal degeneration (21).…”

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confidence: 99%

Determination of Noscapine’s Localization and Interaction with the Tubulin‐α/β Heterodimer

Alisaraie

Tuszyński

2011

Chem Biol Drug Des

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Noscapine, the benzylisoquinoline alkaloid, 5-(4,5-Dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium, has been extensively used as a cough-suppressing medication with low toxicity. It has been recently shown to also have anti-cancer activity in mice and humans. In this work, using in silico analyses, the most probable binding site for noscapine is identified to be at the intradimer region of the α and β subunits of the tubulin heterodimer. By utilization of small molecule docking techniques, and an analysis of the thermodynamically favorable binding modes of noscapine in its binding site, the key residues of tubulin monomers interacting with noscapine are determined. Upon noscapine binding, the conformational change in the tubulin heterodimer along with a potential long-range allosteric effect on both the N and E sites is studied by means of molecular dynamics simulations. Noscapine is found to function as a tubulin-stabilizing agent that interacts strongest with the lateral and longitudinal segments of the tubulin dimer, impacting the interaction between monomers in neighboring protofilaments. We infer that this may act as a depolymerization inhibitor of microtubules. As a result of this study, we have designed novel analogues of noscapine with the ultimate goal of finding agents with increased anti-tumor activity and lower inhibitory concentrations than that of noscapine.

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Peloruside, Laulimalide, and Noscapine Interactions with Beta-Tubulin

2012

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This article reviews the recent findings regarding the binding sites, binding modes and binding affinities of three novel antimitotic drugs peloruside, laulimalide and noscapine with respect to tubulin as the target of their action. These natural compounds are shown to bind to β-tubulin and stabilize microtubules for the cases of peloruside A and laulimalide, and prolong the time spent in pause for noscapine. Particular attention is focused on β-tubulin isotypes as targets for new cancer chemotherapy agents and the amino acid differences in the binding site for these compounds between isotypes. We propose a new strategy for antimitotic drug design that exploits differential distributions of tubulin isotypes between normal and cancer cells and corresponding differential affinities between various drug molecules and tubulin isotypes.

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Fixed drug eruption caused by noscapine

Cited by 3 publications

References 5 publications

Update of the Scientific Opinion on opium alkaloids in poppy seeds

Update of the Scientific Opinion on opium alkaloids in poppy seeds

Determination of Noscapine’s Localization and Interaction with the Tubulin‐α/β Heterodimer

Peloruside, Laulimalide, and Noscapine Interactions with Beta-Tubulin

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