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Fig. 1 | Lipids in Health and Disease

Fig. 1

From: Drug triggered pruritus, rash, papules, and blisters – is AGEP a clash of an altered sphingolipid-metabolism and lysosomotropism of drugs accumulating in the skin?

Fig. 1

Lysosomotropism and photosensitizing. Various drugs with supposed lysosomotropism (*), confirmed lysosomotropism (blue), no lysosomotropism (red) [6, 7], and photosensitizing (°) [3] with characteristic cutaneous adverse reactions (rash, urticaria, pruritus, and AGEP) according to their human medicine european public assessment report (EPAR) product information [8] and https://www.drugs.com [26]. Brown circles indicate the nitrogen atoms responsible for lysosomotropism; the orange circles indicate the strongest basic nitrogen atoms in photosensitizing compounds or its metabolites. pKa of the strongest basic nitrogen [27]: duloxetine 9.7, sertraline 9.85, amitriptyline 9.76, ciprofloxacine 8.68, linagliptin 9.86, lisinopril 10.21, metoprolol 9.67, terbinafine 8.86, pregabalin 10.23, ranolanzine 7.17, loratadine 4,33, desloratadine 9,73, amiodarone 8.47, minocycline 8.25, and doxycycline 8.33. High therapeutic dosage (e.g., terbinafine 250 mg/d, ranolazine 750 mg twice per day) may compensate for poor lysosmotropism. (A) Drugs with confirmed (blue) and supposed lysosomotropism (*). (B) Metabolites of drug with supposed lysosomotropism. (C) Photosensitizing drugs hypericin and prominent tetracycline antibiotics with protonatable basic nitrogen atoms, but without lysosomotropism [28]

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Lipids in Health and Disease

ISSN: 1476-511X