Bisoxatin

Identification

Name
Bisoxatin
Accession Number
DB09219
Type
Small Molecule
Groups
Approved
Description

Bisoxatin is a stimulant laxative which increases peristalsis and inhibits absorbtion of water and ions in the intestine [1]. It is marketed in Belgium under the tradename Wylaxine and used for the treatment of constipation and for preparation of the colon for surgical procedures.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Wylaxine (Omega Pharma Belgium)
Categories
UNII
7C75N0L7FP
CAS number
17692-24-9
Weight
Average: 333.343
Monoisotopic: 333.100107967
Chemical Formula
C20H15NO4
InChI Key
BPKUDUSVDVLOPY-UHFFFAOYSA-N
InChI
InChI=1S/C20H15NO4/c22-15-9-5-13(6-10-15)20(14-7-11-16(23)12-8-14)19(24)21-17-3-1-2-4-18(17)25-20/h1-12,22-23H,(H,21,24)
IUPAC Name
2,2-bis(4-hydroxyphenyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one
SMILES
OC1=CC=C(C=C1)C1(OC2=CC=CC=C2NC1=O)C1=CC=C(O)C=C1

Pharmacology

Indication

For use in the treatment of constipation in the absence of bowel obstruction and for surgical preparation of the colon [1].

Pharmacodynamics

Bisoxatin is a stimulant laxative which increases peristalsis and inhibits the absorbtion of water and ions in the intestine [1]. This increases the water content of the feces and increases its movement through the intestine.

Mechanism of action

The precise mechanism of the bisoxatin's stimulant effect and inhibition of water and ion movement is unknown.

Absorption

Once dissociated from acetate, some bisoxatin is absorbed with a Tmax of 4 h [1].

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Absorbed compound is metabolized to bisoxatin glucuronide [1].

Route of elimination

Primarily excreted in the feces 48-72 h after administration as the free parent compound with a small amount remaining as the acetate salt [1]. Bisoxatin glucuronide and a trace amount of parent compound are eliminated in the urine.

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenAcetaminophen may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
AgmatineThe therapeutic efficacy of Bisoxatin can be decreased when used in combination with Agmatine.
AlprazolamAlprazolam may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
Aluminum hydroxideThe therapeutic efficacy of Bisoxatin can be decreased when used in combination with Aluminum hydroxide.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Bisoxatin.
AmiodaroneThe therapeutic efficacy of Bisoxatin can be decreased when used in combination with Amiodarone.
AmitriptylineBisoxatin may decrease the excretion rate of Amitriptyline which could result in a higher serum level.
AmlodipineThe therapeutic efficacy of Bisoxatin can be decreased when used in combination with Amlodipine.
AmoxicillinAmoxicillin may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. FAMPH: Bisoxatin Summary of Product Characteristics [Link]
External Links
PubChem Compound
28689
PubChem Substance
310265126
ChemSpider
26684
ChEBI
135955
Drugs.com
Drugs.com Drug Page
Wikipedia
Bisoxatin
ATC Codes
A06AB09 — Bisoxatin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0201 mg/mLALOGPS
logP3.61ALOGPS
logP3.75ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.79 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.92 m3·mol-1ChemAxon
Polarizability34.26 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Benzoxazinones / Benzomorpholines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Secondary carboxylic acid amides / Lactams / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Diphenylmethane / Benzoxazinone / Benzomorpholine / Benzoxazine / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Oxazinane / Carboxamide group / Lactam
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on October 21, 2015 15:47 / Updated on September 07, 2018 03:25