Chemical Properties
White Powder
Originator
Tinset,Janssen,W. Germany ,1981
Uses
Inhibits the release and actions of leukotrienes
Uses
Orally active anti-allergic agent; related structurally to cinnarizine and having a novel biphasic mode of action
Uses
Orally active anti-allergic agent; related structurally to cinnarizine and having a novel biphasic mode of action.
Definition
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.
Manufacturing Process
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.
Therapeutic Function
Antiallergic
Biological Activity
Oxatomidefound in several antihistaminescan suppress mast cell degranulation. It can be used as an alternative to individuals with allergic rhinitis who do not or poorly respond to more established antihistamines. Oxatomide exhibits both antihistamine and anti-inflammatory properties. It exhibits therapeutic effects against asthma and vulvar lichen sclerosus.''Oxatomide is an anti-allergy compound. It suppresses platelet activating factor (PAF)-induced bronchoconstriction and inhibits leukotriene production.
Synthesis
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 .
