Difenoxin hydrochlorideProduct ingredient for Difenoxin

Name
Difenoxin hydrochloride
Drug Entry
Difenoxin

Difenoxin is a 4-phenylpiperidine which is closely related to the opioid analgesic meperidine. Difenoxin alone is a USA Schedule I controlled drug, as it may be habit forming. However, it is listed as a Schedule IV controlled drug if combined with atropine, which is added to decrease deliberate misuse. Motofen(R) is a brand mixture which combines atropine sulfate and difenoxin hydrochloride. It is approved by the FDA to treat acute and chronic diarrhea.

Difenoxin is an active metabolite of the anti-diarrheal drug, diphenoxylate, which is also used in combination with atropine in the brand mixture Lomotil(R). It works mostly in the periphery and activates opioid receptors in the intestine rather than the central nervous system (CNS). [3] Difenoxin is also closely related to loperamide, but unlike loperamide it is still capable of crossing the blood brain barrier to produce weak sedative and analgesic effects. However, the antidiarrheal potency of difenoxin is much greater than its CNS effects, which makes it an attractive alternative to other opioids.

Accession Number
DBSALT000047
Structure
Synonyms
Difenoxin HCl
UNII
VQZ63K01IW
CAS Number
35607-36-4
Weight
Average: 460.995
Monoisotopic: 460.191755889
Chemical Formula
C28H29ClN2O2
InChI Key
VMIZTXDGZPTKIK-UHFFFAOYSA-N
InChI
InChI=1S/C28H28N2O2.ClH/c29-22-28(24-12-6-2-7-13-24,25-14-8-3-9-15-25)18-21-30-19-16-27(17-20-30,26(31)32)23-10-4-1-5-11-23;/h1-15H,16-21H2,(H,31,32);1H
IUPAC Name
1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid hydrochloride
SMILES
Cl.OC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1
PubChem Compound
37193
ChemSpider
34134
ChEBI
59790
ChEMBL
CHEMBL1200599
Wikipedia
Difenoxin
Predicted Properties
PropertyValueSource
Water Solubility0.00208 mg/mLALOGPS
logP4.39ALOGPS
logP2.65Chemaxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.38Chemaxon
pKa (Strongest Basic)9.41Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area64.33 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity137.24 m3·mol-1Chemaxon
Polarizability47.53 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon