3136. Difenoxin

Nomenclature

CAS number: 28782-42-5
1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic acid; 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotic acid; difenoxilic acid; difenoxylic acid; McN-JR-15403-11; Lyspafen (Cilag-Chemie).
C28H28N2O2; mol wt 424.53.
C 79.22%, H 6.65%, N 6.60%, O 7.54%.

Description and references

Active metabolite of diphenoxylate, q.v., from which it may be prepared by hydrolysis of the ethyl ester: W. Soudijn, I. van Wijngaarden, DE 1953342; eidem, US 3646207 (1970, 1972 to Janssen). Series of articles on pharmacology, toxicology, metabolism: Arzneim.-Forsch. 22, 513-531 (1972). Toxicity data: Niemegeers et al., ibid. 516.

Chemical structure

Derivative

Hydrochloride.

Nomenclature

R-15403.
C28H28N2O2.HCl; mol wt 461.00.
C 72.95%, H 6.34%, N 6.08%, O 6.94%, Cl 7.69%.

Properties

White amorphous power, mp 290°. Very slightly sol in water (0.023%); sparingly sol in chloroform, tetrahydrofuran, dimethylacetamide, DMSO. Stable, can be stored for several years under normal conditions; not hygroscopic; not affected by light. LD50 orally in rats: 149 mg/kg (Niemegeers).

Note

This is a controlled substance (opiate): 21 CFR, 1308.11.

Therapeutic Category

Antiperistaltic; antidiarrheal.

Keywords

Antidiarrheal