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Suplatast tosilate (94055-76-2)

Identification
Name:Suplatast tosilate
Synonyms:Sulfonium,[3-[[4-(3-ethoxy-2-hydroxypropoxy) phenyl]amino]-3-oxopropyl]dimethyl-,salt with 4-methylbenzenesulfonic acid (1:1);Suplatast tosylate;(+-)-(2-((p-(3-Ethoxy-2-hydroxypropoxy)phenyl)carbamoyl)ethyl)dimethylsulfonium p-toluenesulfonate;Tosilato de suplatast [INN-Spanish];IPD-1151T;Sulfonium, (3-((4-(3-ethoxy-2-hydroxypropoxy)phenyl)amino)-3-oxopropyl)dimethyl-, salt with 4-methylbenzenesulfonic acid (1:1);2-[[4-(3-ethoxy-2-hydroxy-propoxy)phenyl]carbamoyl]ethyl-dimethyl-sulfanium; 4-methylbenzenesulfonate;(+-)-(2-(4-(3-Ethoxy-2-hydroxypropoxy)phenyl)carbamoyl)ethyldimethylsulfonium p-tosylate;Ipd 1151T (TN);Ipd 1151T;
CAS:94055-76-2
Molecular Formula: C23H33NO7S2
Molecular Weight: 499.64
InChI: InChI=1/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)
Molecular Structure: (C23H33NO7S2) Sulfonium,[3-[[4-(3-ethoxy-2-hydroxypropoxy) phenyl]amino]-3-oxopropyl]dimethyl-,salt with 4-methylb...
Properties
Flash Point: °C
Boiling Point: °Cat760mmHg
Density:g/cm3
Appearance:white or off-white crystals
Specification:

The IUPAC name of Suplatast tosilate is [3-[4-(3-ethoxy-2-hydroxypropoxy)anilino]-3-oxopropyl]-dimethylsulfanium; 4-methylbenzenesulfonate. With the CAS registry number 94055-76-2, it is also named as (+-)-(2-((p-(3-Ethoxy-2-hydroxypropoxy)phenyl)carbamoyl)ethyl)dimethylsulfonium p-toluenesulfonate; Tosilate de suplatast.   

The other characteristics of this product can be summarized as: (1)#H bond acceptors: 5; (2)#H bond donors: 2; (3)#Freely Rotating Bonds: 11; (4)Rotatable Bond Count: 10; (5)Tautomer Count: 2; (6)Exact Mass: 499.169844; (7)MonoIsotopic Mass: 499.169844; (8)Topological Polar Surface Area: 134; (9)Heavy Atom Count: 33; (10)Complexity: 500; (11)Undefined Atom StereoCenter Count: 1; (12)Covalently-Bonded Unit Count: 2.

Preparation of Suplatast tosilate: Condensating 3-(methylmercapto)propionyl chloride (I) and 4-(3-ethoxy-2 hydroxypropoxy) aniline (II) by means of triethylamine in DMF gives the corresponding amide (III). Then treating III with methyl p-toluenesulfonate (IV) in dichloromethane.


Uses of Suplatast tosilate: It is used as histamine antagonists and anti-allergic agents. Histamine antagonists mean drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only. Suplatast tosilate as a T helper (Th)2 cytokine inhibitor that inhibits the synthesis of interleukin (IL)-4, IL-5, immunoglobulin (Ig)E production, and local eosinophil accumulation.

People can use the following data to convert to the molecule structure.
1. SMILES: [O-]S(=O)(=O)c1ccc(cc1)C.O=C(Nc1ccc(OCC(O)COCC)cc1)CC[S+](C)C;
2. InChI: InChI=1/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).

The following are the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 2124mg/kg (2124mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
mouse LD50 intravenous 81mg/kg (81mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
mouse LD50 oral > 12500mg/kg (12500mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
rat LD50 intravenous 93mg/kg (93mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
rat LD50 oral > 10gm/kg (10000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.

Biological Activity: Th2 cytokine inhibitor that attenuates IL-2, IL-5 and IL-13 production and has no effect on IFN- γ production. Acts as an immunoregulator that suppresses IgE production, eosinophil infiltration and histamine release. Exhibits antiasthmatic, anti-inflammatory and antifibrotic activity in vivo and is orally active.
Flash Point: °C
Storage Temperature: Store at RT
Usage:Suplatast Tosylate is an antiallergic drug. Suplatast Tosylate inhibits antigen-induced histamine release from mast cells as well as IgE antibody formation. Suplatast Tosylate suppresses interleukin (IL)-4 release from T cells, however in human peripheral basophils, Suplatast Tosylate inhibited the antigen-induced release of IL-13 but not IL-4.
Safety Data
 

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