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Suplatast tosilate

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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]

Suplatast tosilate
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (3-{[4-(3-ethoxy-2-hydroxypropoxy)phenyl]amino}-3-oxopropyl)(dimethyl)sulfonium 4-methylbenzenesulfonate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.220.132 Edit this at Wikidata
Chemical and physical data
FormulaC23H33NO7S2
Molar mass499.64 g·mol−1
3D model (JSmol)
  • CCOCC(COC1=CC=C(C=C1)NC(=O)CC[S+](C)C)O.CC1=CC=C(C=C1)S(=O)(=O)[O-]
  • InChI=1S/C16H25NO4S.C7H8O3S/c1-4-20-11-14(18)12-21-15-7-5-13(6-8-15)17-16(19)9-10-22(2)3;1-6-2-4-7(5-3-6)11(8,9)10/h5-8,14,18H,4,9-12H2,1-3H3;2-5H,1H3,(H,8,9,10) checkY
  • Key:RYVJQEZJUFRANT-UHFFFAOYSA-N checkY

Synthesis

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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

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  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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 
  7. ^ "Suplatast tosilate". Thieme. Retrieved 2024-07-03.
  8. ^ "Suplatast tosilate". chemdrug.com. Retrieved 2024-07-03.

Further reading

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  • 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.


 

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