NAV

Bisoxatin

Identification

Generic Name
Bisoxatin
DrugBank Accession Number
DB09219
Background

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.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 333.343
Monoisotopic: 333.100107967
Chemical Formula
C20H15NO4
Synonyms
  • Bisoxatin
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAbacavir may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Bisoxatin which could result in a higher serum level.
AcetazolamideThe risk or severity of dehydration can be increased when Acetazolamide is combined with Bisoxatin.
Food Interactions
Not Available

Products

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International/Other Brands
Wylaxine (Omega Pharma Belgium)

Categories

ATC Codes
A06AB09 — Bisoxatin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
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Substituents
1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Benzomorpholine / Benzoxazine / Benzoxazinone / Carbonyl group / Carboxamide group / Carboxylic acid derivative
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7C75N0L7FP
CAS number
17692-24-9
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

References

General References
  1. FAMPH: Bisoxatin Summary of Product Characteristics [Link]
PubChem Compound
28689
PubChem Substance
310265126
ChemSpider
26684
ChEBI
135955
ZINC
ZINC000002017901
Drugs.com
Drugs.com Drug Page
Wikipedia
Bisoxatin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-0002-3719000000-80675a9182cffee4ad90
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-30d33f37042e8ea068bc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-d5f2947e5fe49ff143cd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-5319000000-55df61f7eee5cad4e82a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000x-0194000000-13500052d1c28b141f23
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-0920000000-86171fc2578284a00541
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0297-9250000000-304d25c6b8f29a0de70c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.8098169
predicted
DarkChem Lite v0.1.0
[M-H]-178.32356
predicted
DeepCCS 1.0 (2019)
[M+H]+193.1179169
predicted
DarkChem Lite v0.1.0
[M+H]+180.68156
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.4811169
predicted
DarkChem Lite v0.1.0
[M+Na]+187.68132
predicted
DeepCCS 1.0 (2019)

Drug created at October 21, 2015 21:47 / Updated at February 21, 2021 18:52