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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

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
2554
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
138
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
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

PubMed

TitleDatePubMed
In vitro susceptibility of the opportunistic fungus Cryptococcus neoformans to anthelmintic benzimidazoles.
1994 Feb
Susceptibility of Encephalitozoon cuniculi to several drugs in vitro.
1995 Jun
Activity of benzimidazoles against cryptosporidiosis in neonatal BALB/c mice.
1995 Oct
In vitro susceptibilities of the AIDS-associated microsporidian Encephalitozoon intestinalis to albendazole, its sulfoxide metabolite, and 12 additional benzimidazole derivatives.
1997 Dec
Ultrastructural changes in Ascaris suum after oxibendazole treatment.
1998 Feb
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
One season of pasture exposure fails to induce a protective resistance to cyathostomes but increases numbers of hypobiotic third-stage larvae.
2002 Aug
An introductory survey of helminth control practices in south africa and anthelmintic resistance on Thoroughbred stud farms in the Western Cape Province.
2002 Dec
Plasma disposition, faecal excretion and in vitro metabolism of oxibendazole following oral administration in horses.
2002 Feb
Evaluation of tests for anthelmintic resistance in cyathostomes.
2002 Jul 2
Development and validation of a liquid chromatographic-electrospray tandem mass spectrometric multiresidue method for anthelmintics in milk.
2002 Nov 8
HPLC assay for albendazole and metabolites in human plasma for clinical pharmacokinetic studies.
2002 Oct 15
Quantitative chromatographic determination of several benzimidazole anthelmintic molecules in parasite material.
2003 Dec 5
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
Evaluation of a larval development assay (DrenchRite) for the detection of anthelmintic resistance in cyathostomin nematodes of horses.
2004 May 7
Prevalence of anthelmintic resistant cyathostomes on horse farms.
2004 Sep 15
Field studies on endoparasites of Thoroughbred foals on seven farms in central Kentucky in 2004.
2006 Apr
Parasite field study in central Kentucky on thoroughbred foals (born in 2004) treated with pyrantel tartrate daily and other parasiticides periodically.
2007 Feb
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
Restrictions of anthelmintic usage: perspectives and potential consequences.
2009 Sep 25
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
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.
Name Type Language
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
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
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
CFR 21 CFR 520.623
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
WHO-VATC QP52AC57
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
WHO-VATC QP52AC07
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
Code System Code Type Description
CAS
20559-55-1
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
EVMPD
SUB09521MIG
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
MESH
C011321
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
PUBCHEM
4622
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
DAILYMED
022N12KJ0X
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
INN
3437
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
MERCK INDEX
m8305
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY Merck Index
FDA UNII
022N12KJ0X
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
SMS_ID
100000083040
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
WIKIPEDIA
OXIBENDAZOLE
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL1087630
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
NCI_THESAURUS
C66262
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045625
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
RXCUI
1009342
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB04910
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
ECHA (EC/EINECS)
243-877-7
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
NSC
758459
Created by admin on Fri Dec 15 15:40:52 UTC 2023 , Edited by admin on Fri Dec 15 15:40:52 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of OXIBENDAZOLE
NIH
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