suplatast tosilate

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (3-{[4-(3-ethoxy-2-hydroxypropoxy)phenyl]amino}-3-oxopropyl)(dimethyl)sulfonium 4-methylbenzenesulfonate

| image = suplatast tosilate.png

| tradename =

| Drugs.com = {{drugs.com|international|suplatast-tosilate}}

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA =

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| legal_US =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 94055-76-2

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| PubChem = 71773

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 115435

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = C9J89787U1

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01423

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 64811

| chemical_formula =

| C=23 | H=33 | N=1 | O=7 | S=2

| smiles = CCOCC(COC1=CC=C(C=C1)NC(=O)CC[S+](C)C)O.CC1=CC=C(C=C1)S(=O)(=O)[O-]

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RYVJQEZJUFRANT-UHFFFAOYSA-N

}}

Suplatast tosilate (INN) is an inhibitor of cytokine T helper cells.{{cite journal |vauthors=Tamaoki J, Kondo M, Sakai N, etal |title=Effect of suplatast tosilate, a Th2 cytokine inhibitor, on steroid-dependent asthma: a double-blind randomised study. Tokyo Joshi-Idai Asthma Research Group |journal=Lancet |volume=356 |issue=9226 |pages=273–8 | date=July 2000 |pmid=11071181 |doi=10.1016/S0140-6736(00)02501-0|s2cid=25482487 }} Overstimulation of these Th2 cells can lead to an allergic reaction,{{cite journal | vauthors = Zhu J, Paul WE | title = CD4 T cells: fates, functions, and faults | journal = Blood | volume = 112 | issue = 5 | pages = 1557–1569 | date = September 2008 | pmid = 18725574 | pmc = 2518872 | doi = 10.1182/blood-2008-05-078154 }} so the drug is used as an antihistamine.{{cite journal |vauthors=Taniguchi H, Togawa M, Ohwada K, etal |title=Suplatast tosilate, a new type of antiallergic agent, prevents the expression of airway hyperresponsiveness in guinea pigs |journal=European Journal of Pharmacology |volume=318 |issue=2–3 |pages=447–54 | date=December 1996 |pmid=9016937 |doi=10.1016/S0014-2999(96)00810-2}} It has also been used in the treatment of Kimura's disease.{{cite journal |vauthors=Ueda T, Arai S, Amoh Y, Katsuoka K |title=Kimura's disease treated with suplatast tosilate and loratadine |journal=European Journal of Dermatology |volume=21 |issue=6 |pages=1020–1 |year=2011 |pmid=21914581 |doi=10.1684/ejd.2011.1539}}{{cite journal |vauthors=Tsukagoshi H, Nagashima M, Horie T, etal |title=Kimura's disease associated with bronchial asthma presenting eosinophilia and hyperimmunoglobulinemia E which were attenuated by suplatast tosilate (IPD-1151T) |journal=Internal Medicine |volume=37 |issue=12 |pages=1064–7 | date=December 1998 |pmid=9932643 |doi=10.2169/internalmedicine.37.1064|doi-access=free }}

Synthesis

:upright=2

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.{{cite patent |country=US |number=4556737 |inventor=Akihide Koda, et al. |status=patent |gdate=1985-12-03 |fdate=1984-02-07 |pridate=1984-01-18 |title=Sulfonium compounds, processes for preparing the compounds and pharmacological composiitons containing the same |assign1=Taiho Pharmaceutical Co Ltd}}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-19-0114 |title=Suplatast tosilate |publisher=Thieme |access-date=2024-07-03}}{{cite web |url=https://www.chemdrug.com/article/8/3284/16419973.html |title=Suplatast tosilate |website=chemdrug.com |access-date=2024-07-03 }}

References

{{Reflist}}

Further reading

  • {{cite journal |author=Sano Y |title=[Anti-inflammatory drugs for the treatment of bronchial hyperresponsiveness] |language=ja |journal=Nihon Kyōbu Shikkan Gakkai Zasshi |volume=34 Suppl |pages=48–53 | date=December 1996 |pmid=9216184}}

Category:Sulfonium compounds

Category:Anilides

Category:Ethoxy compounds

Category:Phenol ethers

Category:Carboxamides

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