Bisacodyl

Base Information

• Chemical Name: Bisacodyl
• CAS No.: 603-50-9
• Molecular Formula: C22H19NO4
• Molecular Weight: 361.397
• Hs Code.: 2933399090
• European Community (EC) Number: 210-044-4
• NSC Number: 755914,614826
• UNII: 10X0709Y6I
• DSSTox Substance ID: DTXSID1022681
• Nikkaji Number: J3.307C
• Wikipedia: Bisacodyl
• Wikidata: Q417874
• NCI Thesaurus Code: C28870
• RXCUI: 1596
• Metabolomics Workbench ID: 152092
• ChEMBL ID: CHEMBL942
• Mol file: 603-50-9.mol

Synonyms:Phenol,4,4'-(2-pyridinylmethylene)bis-, diacetate (ester) (9CI);Phenol,4,4'-(2-pyridylmethylene)di-, diacetate (6CI,7CI);Phenol,4,4'-(2-pyridylmethylene)di-, diacetate (ester) (8CI);4,4'-(2-Pyridylmethylene)diphenol diacetate;Bicol;Bis(p-acetoxyphenyl)-2-pyridylmethane;Bisacodyl;Brocalax;Broxalax;Contralax;Correctol Caplets;Dulcolan;Durolax;Eulaxan;Godalax;Hillcolax;Ivilax;Laco;Laxanin N;Laxine;Laxorex;Neolax;Perilax;Prepacol;Pyrilax;SK-Bisacodyl;Ulcol;Zetrax;

Chemical Property of Bisacodyl

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 138 °C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 492.333 °C at 760 mmHg
• PKA: 4.69±0.10(Predicted)
• Flash Point: 251.554 °C
• PSA: 65.49000
• Density: 1.2 g/cm³
• LogP: 4.11240
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute mineral acids.
• Water Solubility.: Soluble in alcohol (slightly), ether (slightly), chloroform, and acetone. Insoluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 361.13140809
• Heavy Atom Count: 27
• Complexity: 457

Purity/Quality:

99% ^*data from raw suppliers

Bisacodyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: CC(=O)OC1=CC=C(C=C1)C(C2=CC=C(C=C2)OC(=O)C)C3=CC=CC=N3
• Recent ClinicalTrials: A Study to Evaluate the Drug Levels of BMS-986166 in Healthy Male Participants
• Recent EU Clinical Trials: Placebo-controlled crossover study of the ability of Naloxegol to reverse opioid effect on colonic motor patterns in healthy volunteers
• Uses: Cathartic. Stimulant laxative. Bisacodyl is used in the inhibition of (Na+K)ATPase, the increase of mucosal PGE2, and the activation of adenyl cyclase in rat intestine studies. It is used as a laxative drug. It is typically prescribed for relief of constipation.
• Clinical Use: Laxative
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Bisacodyl

There total 14 articles about Bisacodyl 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%

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + acetic anhydride (108-24-7) → bisacodyl (603-50-9)

Guidance literature:

With sodium acetate; at 100 - 140 ℃; Temperature; Large scale;

Reference yield: 74.0%

acetic anhydride (108-24-7) + 3-(4-methoxyphenyl)-[l,2,3]triazolo[1,5-a]pyridine (78539-92-1) + (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (159191-56-7) → bisacodyl (603-50-9)

Guidance literature:

3-(4-methoxyphenyl)-[l,2,3]triazolo[1,5-a]pyridine; (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid; With potassium carbonate; In benzene; at 20 ℃; for 10h; UV-irradiation;

With hydrogen bromide; acetic acid; Reflux;

acetic anhydride; With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1039/c9sc02448d

Reference yield:

pyridine-2-carbaldehyde (1121-60-4) → bisacodyl (603-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: concentrated sulfuric acid

2: sodium acetate

With sulfuric acid; sodium acetate;

upstream raw materials:

4,4'-(2-pyridylmethylene)diphenol

acetic anhydride

pyridine-2-carbonyl chloride

2-Picolinic acid

Downstream raw materials:

4,4'-(2-pyridylmethylene)diphenol

Refernces

• 1、 -. "Synthetic method of 4,4'-(2-pyridylmethylene)diphenol diacetate". Paragraph 0014; 0025; 0028; 0029; 0032; 0033; 0036. . Retrieved 2018/11/22.