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

Molecular Formula	C12H15N3O3
Molecular Weight	249.2658
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Activity of benzimidazoles against cryptosporidiosis in neonatal BALB/c mice.	1995 Oct	7472880
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
Continuance of studies on Population S benzimidazole-resistant small strongyles in a Shetland pony herd in Kentucky: effect of pyrantel pamoate (1992-1999).	2001 Jan 20	11137272
One season of pasture exposure fails to induce a protective resistance to cyathostomes but increases numbers of hypobiotic third-stage larvae.	2002 Aug	12197113
An introductory survey of helminth control practices in south africa and anthelmintic resistance on Thoroughbred stud farms in the Western Cape Province.	2002 Dec	12665133
Plasma disposition, faecal excretion and in vitro metabolism of oxibendazole following oral administration in horses.	2002 Feb	12002632
Evaluation of tests for anthelmintic resistance in cyathostomes.	2002 Jul 2	12079739
Development and validation of a liquid chromatographic-electrospray tandem mass spectrometric multiresidue method for anthelmintics in milk.	2002 Nov 8	12462609
HPLC assay for albendazole and metabolites in human plasma for clinical pharmacokinetic studies.	2002 Oct 15	12367706
Quantitative chromatographic determination of several benzimidazole anthelmintic molecules in parasite material.	2003 Dec 5	14630366
Transtegumental diffusion of benzimidazole anthelmintics into Moniezia benedeni: correlation with their octanol-water partition coefficients.	2003 Jan-Feb	12810040
Population-S benzimidazole- and tetrahydropyrimidine-resistant small strongyles in a pony herd in Kentucky (1977-1999): effects of anthelmintic treatment on the parasites as determined in critical tests.	2003 Nov	14530968
Evaluation of a larval development assay (DrenchRite) for the detection of anthelmintic resistance in cyathostomin nematodes of horses.	2004 May 7	15110410
Prevalence of anthelmintic resistant cyathostomes on horse farms.	2004 Sep 15	15485051
Field studies on endoparasites of Thoroughbred foals on seven farms in central Kentucky in 2004.	2006 Apr	16385405
Comparative study of sample preparation methods; supported liquid membrane and solid phase extraction in the determination of benzimidazole anthelmintics in biological matrices by liquid chromatography-electrospray-mass spectrometry.	2006 Mar 15	18970561
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
The little-known scenario of anthelmintic resistance in equine cyathostomes in Italy.	2008 Dec	19120201
Evaluation of parasiticidal activity of fenbendazole, ivermectin, oxibendazole, and pyrantel pamoate in horse foals with emphasis on ascarids (Parascaris equorum) in field studies on five farms in Central Kentucky in 2007.	2008 Jul	18470536
Field studies indicating reduced activity of ivermectin on small strongyles in horses on a farm in Central Kentucky.	2008 Jun	18389281
Species-specific identification of equine cyathostomes resistant to fenbendazole and susceptible to oxibendazole and moxidectin by macroarray probing.	2009 Jan	18950625
Diagnosis and control of anthelmintic-resistant Parascaris equorum.	2009 Sep 25	19778469
Restrictions of anthelmintic usage: perspectives and potential consequences.	2009 Sep 25	19778468
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
Anthelmintic resistance in cyathostomin populations from horse yards in Italy, United Kingdom and Germany.	2009 Sep 25	19778463
Equine cyathostomins: a review of biology, clinical significance and therapy.	2009 Sep 25	19778462
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.	2010 Feb 3	20128898
Stimulation of pro-inflammatory responses by mebendazole in human monocytic THP-1 cells through an ERK signaling pathway.	2011 Mar	20848085
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
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:40:52 GMT 2023` Edited by `admin` on `Fri Dec 15 15:40:52 GMT 2023`
Record UNII	022N12KJ0X
Record Status	`Validated (UNII)`
Record Version

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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