Suplatast Tosilate

Base Information

• Chemical Name: Suplatast Tosilate
• CAS No.: 94055-76-2
• Molecular Formula: C23H33NO7S2
• Molecular Weight: 499.65
• European Community (EC) Number: 692-147-8
• UNII: C9J89787U1
• DSSTox Substance ID: DTXSID9045003
• Wikipedia: Suplatast_tosilate
• Wikidata: Q7644399
• NCI Thesaurus Code: C152475
• ChEMBL ID: CHEMBL115435
• Mol file: 94055-76-2.mol

Synonyms:(2-(4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoyl)ethyl)dimethylsulfonium p-toluenesulfonate;IPD 1151T;IPD-1151T;suplatast tosilate

Chemical Property of Suplatast Tosilate

Chemical Property:

• Appearance/Colour: white or off-white crystals
• Melting Point: 84-87 °C
• PSA: 158.67000
• LogP: 3.72220
• Storage Temp.: Store at RT
• Solubility.: DMSO: >20mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 499.16984474
• Heavy Atom Count: 33
• Complexity: 500

Purity/Quality:

99% ^*data from raw suppliers

Suplatast Tosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOCC(COC1=CC=C(C=C1)NC(=O)CC[S+](C)C)O.CC1=CC=C(C=C1)S(=O)(=O)[O-]
• Recent EU Clinical Trials: A Phase 2, Randomized, Double-Blind, Placebo-Controlled Study of YM672 in the Treatment of Painful Bladder Syndrome/Interstitial Cystitis
• Recent NIPH Clinical Trials: A prospective, randomized, single- blind, controlled study to investigate the effect of suplatast tosilate on early- stage idiopathic pulmonary fibrosis
• Description: Suplatast tosylate is a unique dimethylsulfonium salt marketed in Japan for the treatment of bronchial asthma, atopic dermatitis and allergic rhinitis. Suplatast tosylate is a potent inhibitor of IgE synthesis without suppressing IgM and IgG. The mechanism of action for suplatast tosylate is thought to be via the inhibition of interleukin-4 and interleukin-6 production by T-cells at the gene level. In allergic patients, suplatast tosylate markedly improved clinical symptoms which correlated with a significant decrease in serum IgE antibody levels. Suplatast is an antiallergic agent. It inhibits IL-4 and IL-5 production in conalbumin-stimulated D10.G4.1 murine T helper 2 (Th2) cells in a concentration-dependent manner. Suplatast (100 mg/kg) inhibits ovalbumin-induced increases in eosinophil and total cell numbers, as well as IL-4, IL-5, and IL-13, but not IFN-γ, levels in bronchoalveolar lavage fluid (BALF) in an ovalbumin-sensitized mouse model of asthma. It also inhibits ovalbumin-induced increases in ovalbumin-specific IgE in serum and bronchial hyperresponsiveness to methacholine in the ovalbumin-sensitized mouse model of asthma.
• Uses: 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. Suplatast Tosilate is a novel capsular anti-asthmatic agent that suppresses both IgE production, IL-4 and IL-5 synthesis with IC50 above 100 μM.

Technology Process of Suplatast Tosilate

There total 12 articles about Suplatast Tosilate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

methyl p-toluene sulfonate (80-48-8) + 2-{4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoyl}ethyl methyl sulfide (160114-16-9,160114-21-6,94057-02-0) → suplatast tosilate (94055-76-2)

Guidance literature:

at 20 - 60 ℃;

Reference yield: 83.0%

C5H11O2S(1+)*C7H7O3S(1-) + C10H15NO3 → suplatast tosilate (94055-76-2)

Guidance literature:

C₅H₁₁O₂S⁽¹⁺⁾*C₇H₇O₃S^(1-); With 1,1'-carbonyldiimidazole; In acetone; at 20 - 30 ℃; for 2h;

C₁₀H₁₅NO₃; In acetone; at 20 - 30 ℃; for 4h;

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → suplatast tosilate (94055-76-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) pyridine, 2.) aq. KOH / 1.) 90 deg C, 6 h, 2.) acetone, RT, 2 h

2: H₂SO₄ / 6 h / 80 °C

3: H₂ / 10percent Pd/C / ethanol / 8 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 3 h / 10 °C

5: CH₂Cl₂ / 120 h / Ambient temperature

With pyridine; potassium hydroxide; sulfuric acid; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jm970285z

upstream raw materials:

methyl p-toluene sulfonate

2-{4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoyl}ethyl methyl sulfide

4-nitro-phenol

4-nitrophenyl 2-oxiranylmethyl ether

Refernces

• 1、 -. "Preparation method of metasulfonate". Paragraph 0006; 0026-0028. . Retrieved 2021/03/30.
• 2、 Tada, Yukio,Yamawaki, Ichiro,Ueda, Shuichi,Matsumoto, Hiroshi,Matsuura, Naosuke,Yasumoto, Mitsugi,Koda, Akihide,Hori, Mikio. "Synthesis and antiallergic activity of dimethyl-2- (phenylcarbamoyl)ethylsulfonium p-toluenesulfonate derivatives". . p. 3330 - 3336. Retrieved 2007/10/03.