Suplatast Tosilate
Basic information
- CAS
94055-76-2- Standard SMILES
CCOCC(O)COc1ccc(NC(=O)CC[S+](C)C)cc1.Cc1ccc(S(=O)(=O)[O-])cc1- InChIKey
RYVJQEZJUFRANT-UHFFFAOYSA-N- Molecular formula
- C23H33NO7S2
- Average molar mass
- 499.6 g/mol
- Monoisotopic mass
- 499.16984474
Overview
structure given in first source; inhibits antigen-produced histamine release from mast cells; inhibits IgE antibody formation
Names & identifiers
- Preferred name
- Suplatast Tosilate
- IUPAC
- [3-[4-(3-ethoxy-2-hydroxypropoxy)anilino]-3-oxopropyl]-dimethylsulfanium;4-methylbenzenesulfonate
- English name
- Suplatast tosilate
- Molecular formula
- C23H33NO7S2
- Molecular weight
- 499.64062
Names & synonyms
Suplatast TosilateSuplatast tosylate94055-76-2IPD-1151TTosilate de suplatastTosilato de suplatastDTXSID9045003C9J89787U1DTXCID7025003(2-(4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoyl)ethyl)dimethylsulfonium p-toluenesulfonateSulfonium, (3-((4-(3-ethoxy-2-hydroxypropoxy)phenyl)amino)-3-oxopropyl)dimethyl-, salt with 4-methylbenzenesulfonic acid (1:1)suplatasti tosilas
Show more names
SuplatastSuplatast Tosylate >Methotrexate Impurity 47Suplatast tosilate USP/EP/BPSuplatast Tosylate (IPD 1151T)TIANFU CHEM--Suplatast tosilate
RefChem:890059Suplatast (Tosilate)Ipd 1151TSuplatast tosilate [INN]MFCD00867604(3-((4-(3-ethoxy-2-hydroxypropoxy)phenyl)amino)-3-oxopropyl)dimethylsulfonium 4-methylbenzenesulfonateSuplatasttosilate[3-[4-(3-ethoxy-2-hydroxypropoxy)anilino]-3-oxopropyl]-dimethylsulfanium;4-methylbenzenesulfonate
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 134 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 10
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 500
Physicochemical properties
- Melting point
- 84 · 84-87°C
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 20 mg/mL · DMSO: >20mg/mL
- form
- powder
- color
- white to off-white
- Merck
- 14 · 14,9003
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
- 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)
- InChIKey
- RYVJQEZJUFRANT-UHFFFAOYSA-N
- SMILES
- C1(NC(=O)CC[S+](C)C)=CC=C(OCC(O)COCC)C=C1.C1(S([O-])(=O)=O)=CC=C(C)C=C1
- CAS DataBase Reference
- 94055 · 94055-76-2(CAS DataBase Reference)
- FDA UNII
- 9 J89787U1 · C9J89787U1
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesRepr. 2 (100%)
Safety data
- wgk
- 3
- rtecs
- WR7906000
- hs_code
- 2930.90.2900
- Toxicity
- LD50 in male, female mice, male, female rats (mg/kg): 81, 96, 96, 93 i.v.; in mice, rats (g/kg): >12.5, >10 orally (Yamashita)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
Applications
DescriptionSuplatast 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.
DescriptionSuplatast 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.
UsesSuplatast 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.
UsesSuplatast Tosilate is a novel capsular anti-asthmatic agent that suppresses both IgE production, IL-4 and IL-5 synthesis with IC50 above 100 μM.
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