NAV

Oxfendazole

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Oxfendazole
DrugBank Accession Number
DB11446
Background

Oxfendazole is a sulfoxide metabolite of fenbendazole. This benzimidazole antihelminthic protects livestock from roundworm. strongyles, and pinworn.

Type
Small Molecule
Groups
Investigational, Vet approved
Structure
3D
Similar Structures
Weight
Average: 315.347
Monoisotopic: 315.067761987
Chemical Formula
C15H13N3O3S
Synonyms
  • (5-(phenylsulfinyl)-1H-benzimidazol-2-yl)carbamic acid methyl ester
  • 5-(phenylsulfinyl)-2-benzimidazolecarbamic acid methyl ester
  • 5-phenylsulfinyl-2-carbomethoxyaminobenzimidazole
  • Fenbendazole S-oxide
  • Fenbendazole sulfoxide
  • Fenbendazole sulphoxide
  • OFDZ
  • Oxfendazole
External IDs
  • RS-8858

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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.
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MethotrexateThe excretion of Methotrexate can be decreased when combined with Oxfendazole.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Not Available
Direct Parent
Benzimidazoles
Alternative Parents
Phenyl sulfoxides / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Carboximidic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Monocyclic benzene moiety
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carbamate ester, sulfoxide, benzimidazoles (CHEBI:35812)
Affected organisms
Not Available

Chemical Identifiers

UNII
OMP2H17F9E
CAS number
53716-50-0
InChI Key
BEZZFPOZAYTVHN-UHFFFAOYSA-N
InChI
InChI=1S/C15H13N3O3S/c1-21-15(19)18-14-16-12-8-7-11(9-13(12)17-14)22(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)
IUPAC Name
methyl N-[5-(benzenesulfinyl)-1H-1,3-benzodiazol-2-yl]carbamate
SMILES
COC(=O)NC1=NC2=CC(=CC=C2N1)S(=O)C1=CC=CC=C1

References

General References
  1. Guinan JJ: Oxfendazole treatment of horses. Aust Vet J. 1983 Jun;60(6):193-4. [Article]
  2. Rowlands DT, Shepherd MT, Collins KR: The oxfendazole pulse release bolus. J Vet Pharmacol Ther. 1988 Dec;11(4):405-8. [Article]
  3. Middelberg A, McKenna PB: Oxfendazole resistance in Nematodirus spathiger. N Z Vet J. 1983 May;31(5):65-6. [Article]
  4. Jones PG: Oxfendazole and ivermectin in calves. Vet Rec. 1988 Feb 6;122(6):143-4. [Article]
  5. Marriner SE, Bogan JA: Pharmacokinetics of oxfendazole in sheep. Am J Vet Res. 1981 Jul;42(7):1143-5. [Article]
  6. Kingsbury PA, Rowlands DT, Reid JF: Anthelmintic activity of oxfendazole in pigs. Vet Rec. 1981 Jan 3;108(1):10-1. [Article]
  7. Soraci AL, Mestorino N, Errecalde JO: Some pharmacokinetic parameters of oxfendazole in sheep. Vet Res Commun. 1997 May;21(4):283-7. [Article]
  8. Webb RF, McCully CH: Resistance of Haemonchus contortus to oxfendazole. Aust Vet J. 1979 Jul;55(7):347-8. [Article]
  9. Morgan DW: Toxicity study of oxfendazole in pregnant sows. Vet Rec. 1982 Aug 21;111(8):161-3. [Article]
  10. Ortiz P, Terrones S, Cabrera M, Hoban C, Ceballos L, Moreno L, Canton C, Donadeu M, Lanusse C, Alvarez L: Oxfendazole flukicidal activity in pigs. Acta Trop. 2014 Aug;136:10-3. doi: 10.1016/j.actatropica.2014.03.024. Epub 2014 Apr 5. [Article]
  11. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
Human Metabolome Database
HMDB0031812
KEGG Drug
D05291
ChemSpider
37316
BindingDB
50300124
RxNav
32634
ChEBI
35812
ChEMBL
CHEMBL42442
Wikipedia
Oxfendazole

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Not Yet RecruitingTreatmentTrichuriasis1
2Not Yet RecruitingTreatmentTrichuris Infection1
2WithdrawnTreatmentHelminthiasis1
1CompletedTreatmentFilariasis1
1CompletedTreatmentHelminthic infection1
1CompletedTreatmentNeurocysticercosis1
1WithdrawnTreatmentTenia Solium Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.387 mg/mLALOGPS
logP2.16ALOGPS
logP2.62Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.26Chemaxon
pKa (Strongest Basic)3.57Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area84.08 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity84.98 m3·mol-1Chemaxon
Polarizability32.4 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0009000000-b75f3a06f0da46a11658
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0569000000-1ffed3cf65a96a10e68b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4l-0950000000-c9aa9d43cb60924d738a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0930000000-21e6ac8aab5ac86d0492
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0920000000-107b63eb5ae48e71a66f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014s-0900000000-4e25d758cb49f67ae07e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-066u-2965000000-a70e1a64ce45c89ae19a

Drug created at February 25, 2016 18:50 / Updated at February 21, 2021 18:53