Suplatast tosilate
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AHFS/Drugs.com | International Drug Names |
Routes of administration | Oral |
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ECHA InfoCard | 100.220.132 |
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Formula | C23H33NO7S2 |
Molar mass | 499.64 g·mol−1 |
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Suplatast tosilate (INN) is an inhibitor of cytokine T helper cells.[1] Overstimulation of these Th2 cells can lead to an allergic reaction,[2] so the drug is used as an antihistamine.[3] It has also been used in the treatment of Kimura's disease.[4][5]
Synthesis
[edit]Acylation of 1-(4-aminophenoxy)-3-ethoxypropan-2-ol (1) with 3-methylthiopropionyl chloride (2) gives the amide (3). Methylation of the thioether using methyl tosylate (4) yields suplatast as its toluenesulfonic acid salt.[6][7][8]
References
[edit]- ^ Tamaoki J, Kondo M, Sakai N, et al. (July 2000). "Effect of suplatast tosilate, a Th2 cytokine inhibitor, on steroid-dependent asthma: a double-blind randomised study. Tokyo Joshi-Idai Asthma Research Group". Lancet. 356 (9226): 273–8. doi:10.1016/S0140-6736(00)02501-0. PMID 11071181. S2CID 25482487.
- ^ Zhu J, Paul WE (September 2008). "CD4 T cells: fates, functions, and faults". Blood. 112 (5): 1557–1569. doi:10.1182/blood-2008-05-078154. PMC 2518872. PMID 18725574.
- ^ Taniguchi H, Togawa M, Ohwada K, et al. (December 1996). "Suplatast tosilate, a new type of antiallergic agent, prevents the expression of airway hyperresponsiveness in guinea pigs". European Journal of Pharmacology. 318 (2–3): 447–54. doi:10.1016/S0014-2999(96)00810-2. PMID 9016937.
- ^ Ueda T, Arai S, Amoh Y, Katsuoka K (2011). "Kimura's disease treated with suplatast tosilate and loratadine". European Journal of Dermatology. 21 (6): 1020–1. doi:10.1684/ejd.2011.1539. PMID 21914581.
- ^ Tsukagoshi H, Nagashima M, Horie T, et al. (December 1998). "Kimura's disease associated with bronchial asthma presenting eosinophilia and hyperimmunoglobulinemia E which were attenuated by suplatast tosilate (IPD-1151T)". Internal Medicine. 37 (12): 1064–7. doi:10.2169/internalmedicine.37.1064. PMID 9932643.
- ^ US patent 4556737, Akihide Koda, et al., "Sulfonium compounds, processes for preparing the compounds and pharmacological composiitons containing the same", issued 1985-12-03, assigned to Taiho Pharmaceutical Co Ltd
- ^ "Suplatast tosilate". Thieme. Retrieved 2024-07-03.
- ^ "Suplatast tosilate". chemdrug.com. Retrieved 2024-07-03.
Further reading
[edit]- Sano Y (December 1996). "[Anti-inflammatory drugs for the treatment of bronchial hyperresponsiveness]". Nihon Kyōbu Shikkan Gakkai Zasshi (in Japanese). 34 Suppl: 48–53. PMID 9216184.