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
Structure for Difenoxin hydrochloride (DBSALT000047)
- 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
- External Links
- PubChem Compound
- 37193
- ChemSpider
- 34134
- ChEBI
- 59790
- ChEMBL
- CHEMBL1200599
- Wikipedia
- Difenoxin
- Predicted Properties
Property Value Source Water Solubility 0.00208 mg/mL ALOGPS logP 4.39 ALOGPS logP 2.65 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 3.38 Chemaxon pKa (Strongest Basic) 9.41 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 64.33 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 137.24 m3·mol-1 Chemaxon Polarizability 47.53 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon