3313. Diphenoxylate

Nomenclature

CAS number: 915-30-0
1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic acid ethyl ester; 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotic acid ethyl ester; ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotate; ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylate; 2,2-diphenyl-4-(4-carbethoxy-4-phenylpiperidino)butyronitrile; R-1132.
C30H32N2O2; mol wt 452.59.
C 79.61%, H 7.13%, N 6.19%, O 7.07%.

Description and references

Prepn: Janssen, US 2898340 (1959). Pharmacokinetics and metabolism: Karim et al., J. Pharmacol. Exp. Ther. 177, 546 (1971); Clin. Pharmacol. Ther. 13, 407 (1972). See also Difenoxin, the active metabolite of diphenoxylate. Comprehensive description: D. D. Hung, Anal. Profiles Drug Subs. 7, 149-169 (1978).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 3810-80-8
C30H32N2O2.HCl; mol wt 489.05.
C 73.68%, H 6.80%, N 5.73%, O 6.54%, Cl 7.25%.

Properties

Crystals, mp 220.5-222°. uv max (methanol): 252, 258, 264 nm. Soly in mg/ml at 25°: acetic acid 500; DMF 500; chloroform 360; methanol >50; ethanol 3; water 0.8; hexane 0.5.

Derivative

Mixture of hydrochloride with atropine sulfate.

Nomenclature

Lomotil (Searle); Diarsed (Sanofi Winthrop); Reasec (Janssen).

Note

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

Therapeutic Category

Antiperistaltic; antidiarrheal.

Keywords

Antidiarrheal