Suplatast tosilate

Suplatast tosilate
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (3-{[4-(3-ethoxy-2-hydroxypropoxy)phenyl]amino}-3-oxopropyl)(dimethyl)sulfonium 4-methylbenzenesulfonate;
CAS Number	94055-76-2 ;
PubChem CID	71773;
ChemSpider	64811 ;
UNII	C9J89787U1;
KEGG	D01423 ;
ChEMBL	ChEMBL115435 ;
CompTox Dashboard (EPA)	DTXSID9045003 ;
ECHA InfoCard	100.220.132
Chemical and physical data
Formula	C23H33NO7S2
Molar mass	499.64 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOCC(COC1=CC=C(C=C1)NC(=O)CC[S+](C)C)O.CC1=CC=C(C=C1)S(=O)(=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.^[1] Overstimulation of these T_h2 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

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

^ 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.

Synthesis

References

Further reading