Tinset,Janssen,W. Germany ,1981
Orally active anti-allergic agent; related structurally to cinnarizine and having a novel biphasic mode of action.
Inhibits the release and actions of leukotrienes
ChEBI: 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.
A 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.
Poison 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.
Oxatomide is synthesized
by alkylation of 1-diphenylmethylpiperazine
with 1-(3-chloropropyl)-1,3-dihydro-2Hbenzimidazol-
2-one in the presence of Na2CO3
. In addition to its histamine H1 receptor antagonistic
effect, oxatomide may have mast-cell
stabilizing activities .
