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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 of OXIBENDAZOLE

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

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

CNS Penetrant
2588
Sources: Known to be CNS penetrant in rabbits. Human data not available.
Curator's Comment: http://www.medirabbit.com/EN/Neurology/cuniculi/pyrimethamine.htm

Originator

Approval Year

1981
142
Targets

Targets

Primary TargetPharmacologyConditionPotency
Tubulin alpha chain
3
Target ID: P50719
Gene ID: NA
Gene Symbol: NA
Target Organism: Haemonchus contortus (Barber pole worm)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
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

PubMed

TitleDatePubMed
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013-09-05
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).
2011-10
Stimulation of pro-inflammatory responses by mebendazole in human monocytic THP-1 cells through an ERK signaling pathway.
2011-03
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.
2010-02-03
Diagnosis and control of anthelmintic-resistant Parascaris equorum.
2009-09-25
Restrictions of anthelmintic usage: perspectives and potential consequences.
2009-09-25
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.
2009-09-25
Anthelmintic resistance in cyathostomin populations from horse yards in Italy, United Kingdom and Germany.
2009-09-25
Equine cyathostomins: a review of biology, clinical significance and therapy.
2009-09-25
Species-specific identification of equine cyathostomes resistant to fenbendazole and susceptible to oxibendazole and moxidectin by macroarray probing.
2009-01
The little-known scenario of anthelmintic resistance in equine cyathostomes in Italy.
2008-12
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.
2008-07
Field studies indicating reduced activity of ivermectin on small strongyles in horses on a farm in Central Kentucky.
2008-06
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.
2007-08
Parasite field study in central Kentucky on thoroughbred foals (born in 2004) treated with pyrantel tartrate daily and other parasiticides periodically.
2007-02
Field studies on endoparasites of Thoroughbred foals on seven farms in central Kentucky in 2004.
2006-04
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.
2006-03-15
Prevalence of anthelmintic resistant cyathostomes on horse farms.
2004-09-15
Evaluation of a larval development assay (DrenchRite) for the detection of anthelmintic resistance in cyathostomin nematodes of horses.
2004-05-07
Quantitative chromatographic determination of several benzimidazole anthelmintic molecules in parasite material.
2003-12-05
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.
2003-11
Transtegumental diffusion of benzimidazole anthelmintics into Moniezia benedeni: correlation with their octanol-water partition coefficients.
2003-06-18
An introductory survey of helminth control practices in south africa and anthelmintic resistance on Thoroughbred stud farms in the Western Cape Province.
2002-12
Development and validation of a liquid chromatographic-electrospray tandem mass spectrometric multiresidue method for anthelmintics in milk.
2002-11-08
HPLC assay for albendazole and metabolites in human plasma for clinical pharmacokinetic studies.
2002-10-15
One season of pasture exposure fails to induce a protective resistance to cyathostomes but increases numbers of hypobiotic third-stage larvae.
2002-08
Evaluation of tests for anthelmintic resistance in cyathostomes.
2002-07-02
Plasma disposition, faecal excretion and in vitro metabolism of oxibendazole following oral administration in horses.
2002-02
Continuance of studies on Population S benzimidazole-resistant small strongyles in a Shetland pony herd in Kentucky: effect of pyrantel pamoate (1992-1999).
2001-01-20
Ultrastructural changes in Ascaris suum after oxibendazole treatment.
1998-02
In vitro susceptibilities of the AIDS-associated microsporidian Encephalitozoon intestinalis to albendazole, its sulfoxide metabolite, and 12 additional benzimidazole derivatives.
1997-12
Activity of benzimidazoles against cryptosporidiosis in neonatal BALB/c mice.
1995-10
Susceptibility of Encephalitozoon cuniculi to several drugs in vitro.
1995-06
In vitro susceptibility of the opportunistic fungus Cryptococcus neoformans to anthelmintic benzimidazoles.
1994-02
Patents

Patents

US3574845
1

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 Mon Mar 31 18:05:18 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:18 GMT 2025
Record UNII
022N12KJ0X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTHELCIDE EQ
Preferred Name English
OXIBENDAZOLE
GREEN BOOK   INN   MART.   MI   USAN  
INN   USAN  
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
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
Created by admin on Mon Mar 31 18:05:18 GMT 2025 , Edited by admin on Mon Mar 31 18:05:18 GMT 2025
CFR 21 CFR 520.623
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WHO-VATC QP52AC57
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NCI_THESAURUS C250
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WHO-VATC QP52AC07
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Code System Code Type Description
CAS
20559-55-1
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PRIMARY
EVMPD
SUB09521MIG
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PRIMARY
MESH
C011321
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PRIMARY
PUBCHEM
4622
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PRIMARY
DAILYMED
022N12KJ0X
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PRIMARY
INN
3437
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PRIMARY
MERCK INDEX
m8305
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PRIMARY Merck Index
FDA UNII
022N12KJ0X
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PRIMARY
SMS_ID
100000083040
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PRIMARY
WIKIPEDIA
OXIBENDAZOLE
Created by admin on Mon Mar 31 18:05:18 GMT 2025 , Edited by admin on Mon Mar 31 18:05:18 GMT 2025
PRIMARY
ChEMBL
CHEMBL1087630
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PRIMARY
NCI_THESAURUS
C66262
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PRIMARY
EPA CompTox
DTXSID5045625
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PRIMARY
RXCUI
1009342
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PRIMARY RxNorm
DRUG BANK
DB04910
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PRIMARY
ECHA (EC/EINECS)
243-877-7
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PRIMARY
NSC
758459
Created by admin on Mon Mar 31 18:05:18 GMT 2025 , Edited by admin on Mon Mar 31 18:05:18 GMT 2025
PRIMARY
Related Record Type Details
Structure of ALBENDAZOLE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of OXIBENDAZOLE
ACTIVE MOIETY
NIH
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