It07:Bisacodyl

It07:Bisacodyl
General
Systematic name	(pyridin-2-ylmethylene)di-4,1-phenylene diacetate
Other names	4,4'-Diacetoxydiphenylpyridyl-2-methane; Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate; Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate (ester); Phenol, 4,4'-(2-pyridylmethylene)di-, diacetate; Bicol; Bis(p-acetoxyphenyl)-2-pyridylmethane; 2-(4,4'-Diacetoxydiphenylmethyl)pyridine; (4,4'-Diacetoxydiphenyl)(2-pyridyl)methane; 4,4'-Diacetoxydiphenylpyrid-2-ylmethane; Di-(p-acetoxyphenyl)-2-pyridylmethane; Di-(4-acetoxyphenyl)-2-pyridylmethane; Dulcolan; Dulcolax; Laxans; LA96A; Pyrilax; 4,4'-(2-Pyridylmethylene)diphenol diacetate; Sk-bisacodyl; Theralax; 4,4'-(2-Pyridylmethylene)diphenol diacetate (ester); 4-[[4-(Acetyloxy)phenyl](2-pyridinyl)methyl]phenyl acetate
Molecular formula	C22H19NO4
SMILES	CC(OC(C=C3)=CC=C3C(C2=CC=C(OC(C)=O)C=C2)C1=NC=CC=C1)=O
Molar mass	361.19 g/mol
Appearance	{{{Appearance}}}
CAS number	603-50-9
Properties
Density & phase	{{{Density}}} g/cm³
Solubility in water	{{{Sol_Water}}} g/100 ml (25°C)
Melting point	407 K
Boiling point	{{{Bp}}} K
[1]	2-8°C
Acidity (pKa)	{{{pKa}}}
Basicity (pKb)	{{{pKb}}}
Chiral rotation [α]D	{{{Rotation}}}°
Viscosity	{{{Viscosity}}} cP at 25°C
Structure
Molecular shape	{{{Mol_Shape}}}
Coordination geometry	{{{Coordination}}}
Crystal structure	{{{Crystal_Structure}}}
Dipole moment	{{{DM}}} D
Hazards
MSDS	External MSDS[2]
Main hazards	{{{Hazards}}}
NFPA 704	{{{NFPA}}}
Flash point	{{{Fp}}}°C
R/S statement	R: {{{R-S}}} S: ?
RTECS number	{{{RTECS}}}
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Other anions	{{{Other_anion}}}
Other cations	{{{Ohter_cation}}}
Related compounds	{{{Relative_Compounds}}}
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Structure
Molecular shape	{{{MolShape}}}
Coordination geometry	{{{Coordination}}}
Crystal structure	{{{CrystalStruct}}}
Dipole moment	{{{Dipole}}} D

Introduction

Bisacodyl is a stimulant laxative, which is used in a short term basis to treat constipation. It acts on nerve endings in the walls of the intestine and the rectum. It causes the muscles in the intestine to contract more often and with increased force. When the intestine contracts it moves the gut contents along faster, thereby relieving constipation. It is also used to empty the bowel before surgery or examination procedures such as X-ray procedures using barium enemas. Bisacodyl is available with or without a medical prescription.

Possible side effects

The side effects of bisacodyl on human include:

- stomach cramps

- upset stomach

- diarrhea

- stomach and intestinal irritation

- faintness

- irritation or burning in the rectum (from suppositories)

Consult the doctor if the above symptoms are severe and persist.

Storage

Store tablets in tightly closed containers in cool place.

3D Structure

Bisacodyl

Syntheisis of Bisacodyl

A new method of sythesise bisacodyl is introduced by Mereyala, H. B. and Sambaru, K. on 2005. The key step involves migrating the 2-pyridacyl group of phenyl pyridine-2-carboxylate 4 in AlCl[3] at 160 °C to yield the intermediate 4-hydroxyphenyl (2-pyridyl)ketone. The above reaction is then treated with phenol using H₃PO₄ to give bisacodyl. This method has advantage over the existing literature methods because the starting material, pyridine-2-carboxylic acid is easily available whereas the less stable compound, pyridine-2-carboxaldehyde was normally used previously.

References

1.http://webbook.nist.gov/cgi/cbook.cgi?Name=bisacodyl&Units=SI&cIR=on&cMS=on&cUV=on 2.http://chembank.broad.harvard.edu/chemistry/viewMolecule.htm?cbid=982&desc=* 3.http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a601027.html

4.H. B. Mereyala and K. Sambaru, Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 2005, 44, 615-617.