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
- 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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- 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.
Target Actions Organism UTubulin beta-4B chain Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- 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
- 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]
- Magambo JK: Ultrastructural changes in Ascaris suum after oxibendazole treatment. Afr J Health Sci. 1998 Feb;5(1):38-41. [Article]
- External Links
- PubChem Compound
- 4622
- PubChem Substance
- 175426899
- ChemSpider
- 4461
- BindingDB
- 31048
- 1009342
- ChEBI
- 92907
- ChEMBL
- CHEMBL1087630
- ZINC
- ZINC000004685859
- Wikipedia
- Oxibendazole
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 230 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.347 mg/mL ALOGPS logP 2.07 ALOGPS logP 2.52 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 9.64 Chemaxon pKa (Strongest Basic) 4.56 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 76.24 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 66.66 m3·mol-1 Chemaxon Polarizability 26.98 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9961 Blood Brain Barrier + 0.9398 Caco-2 permeable - 0.6343 P-glycoprotein substrate Non-substrate 0.5548 P-glycoprotein inhibitor I Non-inhibitor 0.8365 P-glycoprotein inhibitor II Non-inhibitor 0.9136 Renal organic cation transporter Non-inhibitor 0.8413 CYP450 2C9 substrate Non-substrate 0.8287 CYP450 2D6 substrate Non-substrate 0.6486 CYP450 3A4 substrate Non-substrate 0.5155 CYP450 1A2 substrate Inhibitor 0.758 CYP450 2C9 inhibitor Non-inhibitor 0.8965 CYP450 2D6 inhibitor Non-inhibitor 0.7517 CYP450 2C19 inhibitor Non-inhibitor 0.8081 CYP450 3A4 inhibitor Non-inhibitor 0.9171 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8601 Ames test Non AMES toxic 0.7022 Carcinogenicity Non-carcinogens 0.9435 Biodegradation Not ready biodegradable 0.9896 Rat acute toxicity 2.6303 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8784 hERG inhibition (predictor II) Non-inhibitor 0.8975
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0gdi-2790000000-36a8e52bd89d68997bca
Targets

- 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
- 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