1196. Bezitramide

Nomenclature

CAS number: 15301-48-1
1-[1-(3-Cyano-3,3-diphenylpropyl)-4-piperidinyl]-1,3-dihydro-3-(1-oxopropyl)-2H-benzimidazol-2-one; 1-[1-(3-cyano-3,3-diphenylpropyl)-4-piperidyl]-3-propionyl-2-benzimidazolinone; 1-(3-cyano-3,3-diphenylpropyl)-4-(2-oxo-3-propionyl-1-benzimidazolinyl)piperidine; benzitramide; R-4845; Burgodin (Janssen).
C31H32N4O2; mol wt 492.61.
C 75.58%, H 6.55%, N 11.37%, O 6.50%.

Description and references

Opioid analgesic. Prepn: BE 633495; P. A. J. Janssen, US 3196157 (1963, 1965 both to Janssen). Pharmacology and clinical data: P. A. J. Janssen et al., Arzneim.-Forsch. 21, 862 (1971); W. K. P. Amery et al., ibid. 868; H. Knape, Anaesthesist 21, 251 (1972).

Chemical structure

Properties

White crystalline powder, mp 145-149°. Also reported as pale yellow amorphous powder, mp 124.5-126°. Solubility of >1 g/100 ml in ethyl acetate, acetone, benzene, chloroform. Almost insol in water, dilute acids. LD50 orally in mice, rats: 2101, 141 mg/kg (Janssen).

Note

This is a controlled substance (opiate): 21 CFR, 1308.12.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Diphenylpropylamine Derivatives