4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide

• ChemBase ID: 715
• Molecular Formular: C29H33ClN2O2
• Molecular Mass: 477.03752
• Monoisotopic Mass: 476.22305599
• SMILES: Clc1ccc(C2(O)CCN(CC2)CCC(c2ccccc2)(c2ccccc2)C(=O)N(C)C)cc1
• Canonical SMILES: Clc1ccc(cc1)C1(O)CCN(CC1)CCC(C(=O)N(C)C)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3
• InChIKey: RDOIQAHITMMDAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
• IUPAC Traditional name: loperamide
• Brand Name: Apo-Loperamide; Diarr-Eze; Imodium; Imodium A-D; Imodium A-D Caplets; Ioperamide; Kaopectate II; Loperacap; Loperamida [INN-Spanish]; Loperamide HCL; Loperamidum [INN-Latin]; Maalox Anti-Diarrheal; Nu-Loperamide; PMS-Loperamide; Pepto Diarrhea Control; Rho-Loperamide
• Synonyms: Loperamide

Database IDs

• CAS Number: 53179-11-6
• PubChem SID: 160964178; 46504591
• PubChem CID: 3955

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.964883
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.4130412
• LogD (pH = 7.4): 2.771404
• Log P: 4.7711906
• Molar Refractivity: 139.319 cm^3
• Polarizability: 54.263134 Å^3
• Polar Surface Area: 43.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.44
• LOG S: -5.74
• Solubility (Water): 8.60e-04 g/l

PROPERTIES

Physical Property

• Solubility: Slight
• Hydrophobicity(logP): 5.5

DETAILS

DrugBank - DB00836

• Drug Groups: approved
• Description: One of the long-acting synthetic antidiarrheals; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally. [PubChem]
• Indication: For the control and symptomatic relief of acute nonspecific diarrhea and of chronic diarrhea associated with inflammatory bowel disease or gastroenteritis. Also used for reducing the volume of discharge from ileostomies.
• Pharmacology: Loperamide is a synthetic anti-diarrheal indicated for the control and symptomatic relief of acute nonspecific diarrhea and of chronic diarrhea associated with inflammatory bowel disease. Loperamide is also indicated for reducing the volume of discharge from ileostomies. In man, Loperamide prolongs the transit time of the intestinal contents. It reduces the daily fecal volume, increases the viscosity and bulk density, and diminishes the loss of fluid and electrolytes. Tolerance to the antidiarrheal effect has not been observed. Loperamide is an opioid receptor agonist and acts on the mu opioid receptors in the myenteric plexus large intestines; it does not affect the central nervous system like other opioids. It works specifically by decreasing the activity of the myenteric plexus which decreases the motility of the circular and longitudinal smooth muscles of the intestinal wall. This increases the amount of time substances stay in the intestine, allowing for more water to be absorbed out of the fecal matter. Loperamide also decreases colonic mass movements and suppresses the gastrocolic reflex.
• Toxicity: Oral, mouse: LD₅₀ = 105 mg/kg. Symptoms of overdose include constipation, drowsiness, lethargy, and nausea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Not significantly absorbed from the gut
• Half Life: 9.1 to 14.4 hours (average 10.8 hours)
• Protein Binding: 97%
• Elimination: Excretion of the unchanged loperamide and its metabolites mainly occurs through the feces.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com