OXIBENDAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H15N3O3
Molecular Weight	249.2658
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCOC1=CC2=C(NC(NC(=O)OC)=N2)C=C1

InChI

InChIKey=RAOCRURYZCVHMG-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB04910

Oxibendazole is an anthelmintics drug which is used to protect against roundworms, strongyles, threadworms, pinworms and lungworm infestations in horses and other domestic pets. 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin alpha chain 3 Target ID: P50719 Gene ID: NA Gene Symbol: NA Target Organism: Haemonchus contortus (Barber pole worm) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3755220	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Roundworm infection 1 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=187996	Curative		Approved 8429	Anthelcide EQ Approved Use Anthelcide EQ Paste is indicated for removal and control of: large strongyles (Strongylus edentatus, S. equinus, S. vulgaris); small strongyles (species of the genera Cylicostephanus, Cylicocyclus, Cyathostomum, Triodontophorus, Cylicodontophorus, and Gyalocephalus); large roundworms (Parascaris equorum); pinworms (Oxyuris equi) including various larval stages; and threadworms (Strongyloides westeri).

PubMed

Title	Date	PubMed
In vitro susceptibility of the opportunistic fungus Cryptococcus neoformans to anthelmintic benzimidazoles.	1994 Feb	8192471
Susceptibility of Encephalitozoon cuniculi to several drugs in vitro.	1995 Jun	7574513
In vitro susceptibilities of the AIDS-associated microsporidian Encephalitozoon intestinalis to albendazole, its sulfoxide metabolite, and 12 additional benzimidazole derivatives.	1997 Dec	9420047
Ultrastructural changes in Ascaris suum after oxibendazole treatment.	1998 Feb	17580993
One season of pasture exposure fails to induce a protective resistance to cyathostomes but increases numbers of hypobiotic third-stage larvae.	2002 Aug	12197113
HPLC assay for albendazole and metabolites in human plasma for clinical pharmacokinetic studies.	2002 Oct 15	12367706
Study (1991 to 2001) of drug-resistant Population B small strongyles in critical tests in horses in Kentucky at the termination of a 40-year investigation.	2007 Aug	17468973
Parasite field study in central Kentucky on thoroughbred foals (born in 2004) treated with pyrantel tartrate daily and other parasiticides periodically.	2007 Feb	17013652
Determination of genomic DNA sequences for beta-tubulin isotype 1 from multiple species of cyathostomin and detection of resistance alleles in third-stage larvae from horses with naturally acquired infections.	2009 Sep 25	19778467
Further evaluation in field tests of the activity of three anthelmintics (fenbendazole, oxibendazole, and pyrantel pamoate) against the ascarid Parascaris equorum in horse foals on eight farms in Central Kentucky (2009-2010).	2011 Oct	21499750

Patents

Sample Use Guides

In Vivo Use Guide

Oxibendazole should be administered orally. The dose depends on species, and constitutes 10-20 mg/kg for dogs, 10-50 mg/kg for cats, 5-15 mg/kg for cattle. 10-15 mg/kg for horses.

Route of Administration: Oral

In Vitro Use Guide

To study binding of oxibendazole to H. contortus tubulin, 10 [3H]oxibendazole (OBZ) was used as a radioligand. Solution was incubated for 15 min at 37°C. Binding was terminated by the addition of a charcoal solution. After 5 min incubation to adsorb unbound drug, the charcoal was sedimented by 5 min centrifugation, and bound [3H]OBZ was counted.

Name

Type

Language

OXIBENDAZOLE

Official Name

English

OXIBENDAZOLE [USAN]

Common Name

English

oxibendazole [INN]

Common Name

English

ALBENDAZOLE IMPURITY I [EP IMPURITY]

Common Name

English

OXIBENDAZOLE [GREEN BOOK]

Common Name

English

NSC-758459

Code

English

OXIBENDAZOLE [MART.]

Common Name

English

OXIBENDAZOLE [MI]

Common Name

English

Methyl 5-propoxy-2-benzimidazolecarbamate

Common Name

English

ANTHELCIDE EQ

Brand Name

English

FILARIBITS PLUS

Brand Name

English

METHYL N-(5-PROPOXY-1H-BENZIMIDAZOL-2-YL)CARBAMATE

Systematic Name

English

SK&F-30310

Code

English

CARBAMIC ACID, (5-PROPOXY-1H-BENZIMIDAZOL-2-YL)-, METHYL ESTER

Systematic Name

English

SK&F 30310

Code

English

Classification Tree Code System Code

CFR

21 CFR 520.1638