Difenoxinum
- CAS No.
- 28782-42-5
- Chemical Name:
- Difenoxinum
- Synonyms
- Difenoxine;Difenoxinum;McN-JR-15403-11;Difenoxylic Acid;Difenoxilic Acid;Diphenoxylic Acid;Difenoxin EP impurity A;Diphenoxylate Impurity A;UFIVBRCCIRTJTN-UHFFFAOYSA-N;Diphenoxylate EP impurity A
- CBNumber:
- CB01178506
- Molecular Formula:
- C28H28N2O2
- Molecular Weight:
- 424.53
- MDL Number:
- MOL File:
- 28782-42-5.mol
| Boiling point | 632.7±55.0 °C(Predicted) |
|---|---|
| Density | 1.175±0.06 g/cm3(Predicted) |
| solubility | soluble in DMSO, Methanol |
| form | Powder |
| pka | 3.55±0.20(Predicted) |
| color | Brown |
| FDA UNII | 3ZZ5BJ9F2Q |
SAFETY
Risk and Safety Statements
| HS Code | 2933330000 |
|---|---|
| Toxicity | rat,LD50,oral,149mg/kg (149mg/kg),Drug Development Research. Vol. 1, Pg. 1, 1981. |
Difenoxinum Chemical Properties,Uses,Production
Originator
Lyspafena,Cilag Chemie,W. Germany,1980
Uses
The active metabolite of Diphenoxylate. Antiperistaltic; antidiarrheal. This is a controlled substance (opiate).
Definition
ChEBI: A piperidinemonocarboxylic acid that is 4-phenylpiperidine-4-carboxylic acid in which the hydrogen attached to the nitrogen atom is substituted by a 3-cyano-3,3-diphenylpropyl group.
Manufacturing Process
To a stirred solution of 5.52 parts of t-potassiurn butanolate in 60 parts of dimethylsulfoxide are added 1.7 parts of ethyl-1-(3-cyano-3,3- diphenylpropyl)-4-phenylisonipecotate hydrochloride and the whole is stirred on an oil bath (90°C) for 4 hours. The reaction mixture is cooled (30°C) and poured onto 180 parts of water with stirring. After two extractions with benzene, the aqueous phase is acidified with glacial acetic acid to pH 6.5 with stirring. The precipitated product is filtered off, washed with water, dried, dissolved in 50 parts of 0.4 N potassium hydroxide and precipitated again with glacial acetic acid. The crude free base is filtered off and dissolved in a mixture of 2-propanol and chloroform and gaseous hydrogen chloride is introduced into the solution. The whole is filtered and the filtrate is evaporated. The residue is mixed with benzene and the latter is evaporated again. The residue is recrystallized from 2-propanol, yielding 1-(3-cyano-3,3- diphenylpropyl)-4-phenylisonipecotic acid hydrochloride.
brand name
Dioctin;Lyspafen;Lyspofenac;Motofen.
Therapeutic Function
Antiperistaltic
World Health Organization (WHO)
Difenoxin is the principal metabolite of diphenoxylate. See WHO comment for diphenoxylate.