Oxatomide

Oxatomide

Systematic (IUPAC) name
1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-1,3-dihydro-2H-benzimidazol-2-one
Clinical data
Trade names	Tinset, Cedlips, Atoxan
AHFS/Drugs.com	International Drug Names
Legal status	℞ (Prescription only)
Routes of administration	Oral
Identifiers
CAS Number	60607-34-3 N
ATC code	R06AE06 (WHO)
PubChem	CID: 4615
ChemSpider	4454 Y
UNII	J31IL9Z2EE Y
KEGG	D01773 Y
ChEMBL	CHEMBL13828 Y
Chemical data
Formula	C27H30N4O
Molecular mass	426.553 g/mol
SMILES O=C2Nc1ccccc1N2CCCN5CCN(C(c3ccccc3)c4ccccc4)CC5
InChI InChI=1S/C27H30N4O/c32-27-28-24-14-7-8-15-25(24)31(27)17-9-16-29-18-20-30(21-19-29)26(22-10-3-1-4-11-22)23-12-5-2-6-13-23/h1-8,10-15,26H,9,16-21H2,(H,28,32) Y Key:BAINIUMDFURPJM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Oxatomide (R35443) is a first-generation antihistamine of the phenylpiperazine class. It was discovered at Janssen Pharmaceutica in 1975. Oxatomide lacks any anticholinergic effects. In addition to its H₁ receptor antagonism, it also possesses antiserotonergic actions.

Synthesis

Oxatomide synthesis:

Reaction of 2-Benzimidazolinone with isopropenyl acetate leads to the singly protected imidazolone derivative (2). Alkylation of this with 3-chloro-1-bromopropane affords the functionalized derivative (3). Alkylation of the monobenzhydryl derivative of piperazine (4) with 3 gives oxatomide (5), after hydrolytic removal of the protecting group.

See also

• Piperazine
• Milenperone, Declenperone.