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Suplatast tosilate

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Chemical compound Pharmaceutical compound
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
IUPAC name
  • (3-{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
3D model (JSmol)
SMILES
  • CCOCC(COC1=CC=C(C=C1)NC(=O)CC(C)C)O.CC1=CC=C(C=C1)S(=O)(=O)
InChI
  • 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)
  • Key:RYVJQEZJUFRANT-UHFFFAOYSA-N

Suplatast tosilate (INN) is an inhibitor of cytokine T helper cells. Overstimulation of these Th2 cells can lead to an allergic reaction, so the drug is used as an antihistamine. It has also been used in the treatment of Kimura's disease.

Synthesis

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.

References

  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

  • Sano Y (December 1996). "". Nihon Kyōbu Shikkan Gakkai Zasshi (in Japanese). 34 Suppl: 48–53. PMID 9216184.


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