Loperamide

Base Information

• Chemical Name: Loperamide
• CAS No.: 53179-11-6
• Molecular Formula: C29H33 Cl N2 O2
• Molecular Weight: 477.046
• Hs Code.: 29252000
• European Community (EC) Number: 258-416-5
• UNII: 6X9OC3H4II
• DSSTox Substance ID: DTXSID6045165
• Nikkaji Number: J10.085D
• Wikipedia: Loperamide
• Wikidata: Q423751
• NCI Thesaurus Code: C618
• RXCUI: 6468
• Pharos Ligand ID: WXFXAH3QBV55
• Metabolomics Workbench ID: 38692
• ChEMBL ID: CHEMBL841
• Mol file: 53179-11-6.mol

Synonyms:Hydrochloride, Loperamide;Imodium;Loperamide;Loperamide Hydrochloride;Loperamide Monohydrochloride;Monohydrochloride, Loperamide;R 18553;R-18553;R18553

Chemical Property of Loperamide

Chemical Property:

• Vapor Pressure: 1.23E-17mmHg at 25°C
• Boiling Point: 647.2 °C at 760 mmHg
• PKA: pKa 8.66(H2O) (Uncertain)
• Flash Point: 345.2 °C
• PSA: 43.78000
• Density: 1.187g/cm³
• LogP: 5.02590
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 476.2230560
• Heavy Atom Count: 34
• Complexity: 623

Purity/Quality:

99.9% ^*data from raw suppliers

Loperamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gastrointestinal Agents; Opioids
• Canonical SMILES: CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4
• Recent ClinicalTrials: A Study of LY2835219 (Abemaciclib) in Combination With Therapies for Breast Cancer That Has Spread
• Recent EU Clinical Trials: A Randomized Phase II Study to Evaluate the Incidence of Discontinuations due to Diarrhoea at 3 Cycles in patients with Early-stage HER2-positive (HER2+), Hormone Receptor-positive (HR+) Breast Cancer treated with Neratinib plus Loperamide prophylaxis versus Neratinib with Initial Dose Escalation plus PRN Loperamide prophylaxis versus Neratinib plus Loperamide plus Colesevelam prophylaxis. “DIANER Study”
• Uses: Loperamide is presently used more often as an antidiarrheal drug than as an analgesic, and it is also included in the list of over-the-counter drugs because of its insignificant action on the CNS. It reduces intestinal smooth muscle tone and motility as a result of binding to intestinal opiate receptors. It is used for symptomatic treatment of severe and chronic diarrhea of various origins. The most popular synonym for loperamide is imodium.
• Therapeutic Function: Antidiarrheal

Technology Process of Loperamide

There total 6 articles about Loperamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

loperamide N-oxide → loperamide (53179-11-6)

Guidance literature:

With sodium tetrahydroborate; In ethanol; water; at 50 - 60 ℃; chemoselective reaction;

DOI:10.1016/j.tetlet.2010.08.045

Reference yield: 80.0%

4-(4-chlorophenyl)-4-hydroxypiperidine (39512-49-7) + N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide (37743-18-3) → loperamide (53179-11-6)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1016/j.bmcl.2004.08.032

Reference yield:

4-Bromo-2,2-diphenylbutyric acid (37742-98-6) → loperamide (53179-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride; dimethylformamide / CHCl₃ / 4 h / Heating

2: Na₂CO₃ / tetrahydrofuran

3: 80 percent / Na₂CO₃ / dimethylformamide / 80 °C

With thionyl chloride; sodium carbonate; N,N-dimethyl-formamide; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.08.032

upstream raw materials:

4-(4-chlorophenyl)-4-hydroxypiperidine

N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide

4-Bromo-2,2-diphenylbutyric acid

4-bromo-2,2-diphenylbutyric acid chloride

Refernces

• 1、 -. "Solid Pharmaceutical Preparations Containing Copolymers Based On Polyethers Combined With Poorly Water-Soluble Polymers". . . Retrieved 2012/03/12.
• 2、 Gowda, Narendra B.,Rao, Gopal Krishna,Ramakrishna, Ramesha A.. "A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water". experimental part. p. 5690 - 5693. Retrieved 2010/11/05.