Oxatomide

Oxatomide Basic information
Product Name:Oxatomide
Synonyms:OXATOMIDE;oxatomida;r35443;tinset;1-[3-[4-(DIPHENYLMETHYL)-1-PIPERAZINYL]PROPYL]-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE;Celtect;Cobiona;Dasten
CAS:60607-34-3
MF:C27H30N4O
MW:426.55
EINECS:262-320-9
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:60607-34-3.mol
Oxatomide Structure
Oxatomide Chemical Properties
Melting point 153.60C
Boiling point 541.98°C (rough estimate)
density 1.1239 (rough estimate)
refractive index 1.6000 (estimate)
storage temp. Refrigerator
solubility DMSO: soluble
pka12.20±0.30(Predicted)
form White solid.
color white
CAS DataBase Reference60607-34-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS DE2276000
ToxicityLD50 in guinea pigs, mice, rats (mg/kg): 320, >2560, >2560 orally; 23, 27, 30 i.v. (Richards)
MSDS Information
ProviderLanguage
Oxatomide English
SigmaAldrich English
Oxatomide Usage And Synthesis
Chemical PropertiesWhite Powder
OriginatorTinset,Janssen,W. Germany ,1981
UsesInhibits the release and actions of leukotrienes
UsesOrally active anti-allergic agent; related structurally to cinnarizine and having a novel biphasic mode of action.
DefinitionChEBI: Oxatomide is a member of the class of benzimidazoles that is 1,3-dihydro-2H-benzimidazol-2-one substituted by a 3-[4-(diphenylmethyl)piperazin-1-yl]propyl group at position 1. It is an anti-allergic drug. It has a role as a geroprotector, a H1-receptor antagonist, an anti-allergic agent, an anti-inflammatory agent and a serotonergic antagonist. It is a N-alkylpiperazine, a member of benzimidazoles and a diarylmethane.
Manufacturing ProcessA mixture of 53 parts of 1-(3chloropropyl)-2H-benzimidazol-2one, 5 parts of 1-(diphenylmethyl)piperazine, 6.4 parts of sodium bicarbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with waterseparator. After cooling, water is added and the layers are separated. The 4methyl-2pentanone phase is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from a mixture of 2,2'-oxybispropane and a small amount of 2-propanol. The product is filtered off and dried, yielding 1-[3-[4-(diphenylmethyl)-1piperazinyl]propyl]-2H-benzimidazole-2-one; melting point 153.6°C.
Therapeutic FunctionAntiallergic
Safety ProfilePoison by ingestion, intraperitoneal, and intravenous routes. An experimental teratogen. Experimental reproductive effects. Used to treat allergies and asthma. When heated to decomposition it emits toxic fumes of NOx.
Chloromethyl isopropyl carbonate Albendazole Imidocarb dipropionate Alkyl benzimidazole Leflunomide Thiabendazole Benzimidazole Cyclopropyl methyl ketone 3-Methyl-2-butanone Oxatomide 1-Methylpiperazine 3-(4-ETHYL-PIPERAZIN-1-YL)-PROPYLAMINE Imidazole Phenformin 1-EBIO benzimidazolone Fenbendazole Dihydromyrcenol

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