NAV

Oxibendazole

Identification

Generic Name
Oxibendazole
DrugBank Accession Number
DB04910
Background

Oxibendazole is a polymerase inhibitor in phase III trials for the treatment of helminth intestinal infections.

Type
Small Molecule
Groups
Investigational, Vet approved
Structure
3D
Similar Structures
Weight
Average: 249.2658
Monoisotopic: 249.111341361
Chemical Formula
C12H15N3O3
Synonyms
  • 5-Propoxy-2-benzimidazolecarbamic acid methyl ester
  • Methyl 5-n-propoxy-2-benzimidazole carbamate
  • Methyl 5-propoxy-2-benzimidazolecarbamate
  • Oxibendazole
  • Oxibendazolo
  • Oxibendazolum
External IDs
  • SK&F 30310
  • SK&F-30310
  • SKF 30310

Pharmacology

Indication

Investigated for use/treatment in infectious and parasitic disease (unspecified) and pediatric indications.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Oxibendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.

TargetActionsOrganism
UTubulin beta-4B chainNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic

Route of elimination

Not Available

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.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Loditac

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
2-benzimidazolylcarbamic acid esters
Direct Parent
2-benzimidazolylcarbamic acid esters
Alternative Parents
Alkyl aryl ethers / Benzenoids / Imidazoles / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
2-benzimidazolylcarbamic acid ester / Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Ether
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Helminthic Microorganisms

Chemical Identifiers

UNII
022N12KJ0X
CAS number
20559-55-1
InChI Key
RAOCRURYZCVHMG-UHFFFAOYSA-N
InChI
InChI=1S/C12H15N3O3/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
IUPAC Name
methyl N-(6-propoxy-1H-1,3-benzodiazol-2-yl)carbamate
SMILES
CCCOC1=CC2=C(C=C1)N=C(NC(=O)OC)N2

References

General References
  1. Gokbulut C, Nolan AM, McKellar QA: Plasma disposition, faecal excretion and in vitro metabolism of oxibendazole following oral administration in horses. Res Vet Sci. 2002 Feb;72(1):11-5. [Article]
  2. Magambo JK: Ultrastructural changes in Ascaris suum after oxibendazole treatment. Afr J Health Sci. 1998 Feb;5(1):38-41. [Article]
PubChem Compound
4622
PubChem Substance
175426899
ChemSpider
4461
BindingDB
31048
RxNav
1009342
ChEBI
92907
ChEMBL
CHEMBL1087630
ZINC
ZINC000004685859
Wikipedia
Oxibendazole

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
PropertyValueSource
melting point (°C)230 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.347 mg/mLALOGPS
logP2.07ALOGPS
logP2.52Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.64Chemaxon
pKa (Strongest Basic)4.56Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area76.24 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity66.66 m3·mol-1Chemaxon
Polarizability26.98 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9961
Blood Brain Barrier+0.9398
Caco-2 permeable-0.6343
P-glycoprotein substrateNon-substrate0.5548
P-glycoprotein inhibitor INon-inhibitor0.8365
P-glycoprotein inhibitor IINon-inhibitor0.9136
Renal organic cation transporterNon-inhibitor0.8413
CYP450 2C9 substrateNon-substrate0.8287
CYP450 2D6 substrateNon-substrate0.6486
CYP450 3A4 substrateNon-substrate0.5155
CYP450 1A2 substrateInhibitor0.758
CYP450 2C9 inhibitorNon-inhibitor0.8965
CYP450 2D6 inhibitorNon-inhibitor0.7517
CYP450 2C19 inhibitorNon-inhibitor0.8081
CYP450 3A4 inhibitorNon-inhibitor0.9171
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8601
Ames testNon AMES toxic0.7022
CarcinogenicityNon-carcinogens0.9435
BiodegradationNot ready biodegradable0.9896
Rat acute toxicity2.6303 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8784
hERG inhibition (predictor II)Non-inhibitor0.8975
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0gdi-2790000000-36a8e52bd89d68997bca

Targets

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Details1. Tubulin beta-4B chain
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Unfolded protein binding
Specific Function
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name
TUBB4B
Uniprot ID
P68371
Uniprot Name
Tubulin beta-4B chain
Molecular Weight
49830.72 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51