U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C12H15N3O3S
Molecular Weight 281.331
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALBENDAZOLE OXIDE

SMILES

CCC[S+]([O-])C1=CC=C2NC(NC(=O)OC)=NC2=C1

InChI

InChIKey=VXTGHWHFYNYFFV-UHFFFAOYSA-N
InChI=1S/C12H15N3O3S/c1-3-6-19(17)8-4-5-9-10(7-8)14-11(13-9)15-12(16)18-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.sigmaaldrich.com/catalog/product/sigma/19953 http://www.nita-farm.com/products/detail.php?ELEMENT_ID=1256

Albendazole oxide (Ricobendazole) is a methylcarbamate benzimidazole with a broad-spectrum anthelmintic activity. Ricobendazole is a key metabolite of albendazole. Ricobendazole has broad spectrum anthelmintic action; the drug is active against adult and immature nematodes (Dictyocaulus, Haemonchus, Ostertagia, Thelazia, Trichostrongylus, Nematodirus, Cooperia, Oesophagostomum, Bunostomum, Chabertia etc.), tapeworms (Moniezia, Avitellinae, Thysaniezia etc.), as well as adult flukes (Fasciola, Paramphistom, and Dicrocoelium), having an egg-killing effect; it reduces pasture contamination with helminth eggs. The mechanism of action of ricobendazole (albendazole sulfoxide), ensuring its anthelmintic activity, is associated with selective inhibition of beta-tubulin polymerization, which leads to the destruction of cytoplasmic microtubules of helminth intestinal cells; it inhibits the processes of glucose transport and disposal, and inhibits the synthesis of ATP; it blocks the movement of secretory granules and other organelles in the muscle cells of worms, disrupting the permeability of cell membranes and muscle innervation, which causes paralysis and death of the parasites. Albendazole oxide has been shown to induce apoptosis in human cancer cell line HT-29, possibly by arresting the cell cycle at the G2/M phase.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
RICAZOL

Approved Use

Ricazol shall be prescribed to cattle and small ruminants in the treatment of nematodosis, cestodiasis and distomiasis. Animal dehelmintization shall be carried out as indicated; for prevention purposes: in spring, before driving out and in autumn, before stall housing.
PubMed

PubMed

TitleDatePubMed
Resistance to benzimidazole and macrocyclic lactone anthelmintics in cattle nematodes in Argentina.
2004 Aug 6
A possible model of benzimidazole binding to beta-tubulin disclosed by invoking an inter-domain movement.
2004 Dec
Therapy for neurocysticercosis.
2004 Jan
[Influence of mobile phase composition on chiral separation of albendazole sulfoxide racemates].
2004 May
Quantitative determination of albendazole metabolites in sheep spermatozoa and seminal plasma by liquid chromatographic analysis with fluorescence detection.
2004 Sep 3
Liver microsomal biotransformation of albendazole in deer, cattle, sheep and pig and some related wild breeds.
2005 Aug
Analytical and semipreparative resolution of enatiomers of albendazole sulfoxide by HPLC on amylose tris (3,5-dimethylphenylcarbamate) chiral stationary phases.
2005 Jan 31
Inhibitory effect of albendazole and its metabolites on cytochromes P450 activities in rat and mouflon in vitro.
2005 Jan-Feb
Preoperative albendazole and scolices viability in patients with hepatic echinococcosis.
2005 Jun
Death related to albendazole-induced pancytopenia: case report and review.
2005 Mar
Physicochemical characterization of ricobendazole: I. Solubility, lipophilicity, and ionization characteristics.
2005 May
Transport of anthelmintic benzimidazole drugs by breast cancer resistance protein (BCRP/ABCG2).
2005 May
Antitumor activity of albendazole against the human colorectal cancer cell line HT-29: in vitro and in a xenograft model of peritoneal carcinomatosis.
2005 May
An in vitro kinetic method for detection of precipitation of poorly soluble drugs.
2005 Nov 4
Pharmacokinetics of ricobendazole after its intravenous, intraruminal and subcutaneous administration in sheep.
2005 Oct
Development and optimization of a rapid HPLC method for analysis of ricobendazole and albendazole sulfone in sheep plasma.
2005 Sep 1
Role of ABC transporters in veterinary drug research and parasite resistance.
2006 Apr
Assessments of pharmacokinetic drug interactions and tolerability of albendazole, praziquantel and ivermectin combinations.
2006 Apr
Interaction of enrofloxacin with breast cancer resistance protein (BCRP/ABCG2): influence of flavonoids and role in milk secretion in sheep.
2006 Aug
Variation among faecal egg counts following natural nematode infection in Scottish Blackface lambs.
2006 Feb
Albendazole trial at 15 or 30 mg/kg/day for subarachnoid and intraventricular cysticercosis.
2006 Feb 14
Enantiomeric separation of chiral sulfoxides by supercritical fluid chromatography.
2006 Jul
Evaluation of the efficacy of albendazole sulphoxide and praziquantel in combination on Taenia crassiceps cysts: in vitro studies.
2006 Mar
A dual anthelmintic treatment strategic scheme for the control of fasciolosis in dairy sheep farms.
2006 Nov
Plasma disposition and faecal excretion of netobimin metabolites and enantiospecific disposition of albendazole sulphoxide produced in ewes.
2006 Oct
Efficacy of nitazoxanide, tizoxanide and tizoxanide/albendazole sulphoxide combination against Taenia crassiceps cysts.
2007 Feb
Pharmacokinetics of albendazole in New Zealand white rabbits: oral versus intraperitoneal administration.
2007 Jan-Feb
Simultaneous determination of albendazole metabolites, praziquantel and its metabolite in plasma by high-performance liquid chromatography-electrospray mass spectrometry.
2007 Jun 28
Absorption and metabolism of albendazole after intestinal ischemia/reperfusion.
2007 May
Pharmacokinetics of albendazole sulfoxide enantiomers administered in racemic form and separately in rats.
2008 Aug
[In vitro observation on albendazole sulfoxide and its enantiomers against Echinococcus granulosus protoscolex].
2008 Dec 30
Determination of albendazole metabolites by direct injection of bovine plasma and multidimensional achiral-chiral high performance liquid chromatography.
2008 Jun 30
Kinetic disposition of albendazole in goats subclinically infected with gastrointestinal nematodes vis-à-vis naive animals following oral and intraruminal administration.
2008 Mar
Albendazole versus praziquantel in the treatment of neurocysticercosis: a meta-analysis of comparative trials.
2008 Mar 12
Determination of albendazole and its metabolites in the muscle tissue of hybrid striped and largemouth bass using liquid chromatography with fluorescence detection.
2008 Mar-Apr
LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus.
2008 May
Diagnosis and treatment of pulmonary cystic hydatidosis.
2008 Oct
Characterization of substrates and inhibitors for the in vitro assessment of Bcrp mediated drug-drug interactions.
2008 Oct
Synthesis and in vitro cysticidal activity of new benzimidazole derivatives.
2009 Apr
Albendazole enantiomeric metabolism and binding to cytosolic proteins in the liver fluke Fasciola hepatica.
2009 Feb
Use of albendazole sulfoxide, albendazole sulfone, and combined solutions as scolicidal agents on hydatid cysts (in vitro study).
2009 Jan 7
Stability of ricobendazole in aqueous solutions.
2009 Jul 12
Pharmacological assessment of netobimin as a potential anthelmintic for use in horses: plasma disposition, faecal excretion and efficacy.
2009 Jun
Effect of age and gender in the pharmacokinetics of albendazole and albendazole sulphoxide enantiomers in goats.
2009 Jun
Diagnostic problems with parasitic and non-parasitic splenic cysts.
2009 May 29
Residue depletion of albendazole and its metabolites in the muscle tissue of large mouth and hybrid striped bass after oral administration.
2009 Nov 13
Effect of ritonavir on the pharmacokinetics of the benzimidazoles albendazole and mebendazole: an interaction study in healthy volunteers.
2009 Oct
Comparative in vitro effect of artemether and albendazole on adult Toxocara canis.
2009 Oct
Liquid chromatography/mass spectrometric identification of benzimidazole anthelminthics metabolites formed ex vivo by Dicrocoelium dendriticum.
2009 Sep
Enantiomeric behaviour of albendazole and fenbendazole sulfoxides in domestic animals: pharmacological implications.
2009 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be injected http://www.nita-farm.com/products/detail.php?ELEMENT_ID=1256
For sheep and cattle dosages of 7.5 to 10 mg/kg bw of albendazole oxide are recommended and should be given at monthly intervals
Route of Administration: Oral
Albendazole oxide inhibited human cancer cell line HT-29 with IC50 2.35 uM
Name Type Language
ALBENDAZOLE OXIDE
INN  
INN  
Official Name English
RS8852
Code English
RICOBENDAZOLE
Common Name English
ALBENDAZOLE SULFOXIDE
MI  
Common Name English
RYCOBEN
Brand Name English
albendazole oxide [INN]
Common Name English
RYCOBENDAZOLE
Common Name English
METHYL 5-(PROPYLSULFINYL)-2-BENZIMIDAZOLECARBAMATE
Common Name English
METHYL N-(5-(PROPYLSULFINYL)-1H-BENZIMIDAZOL-2-YL)CARBAMATE
Systematic Name English
(±)-ALBENDAZOLE SULFOXIDE
Common Name English
RS-8852
Code English
ALBENDAZOLE SULFOXIDE [MI]
Common Name English
ALBENDAZOLE IMPURITY B [EP IMPURITY]
Common Name English
METHYL (5-(PROPYLSULFINYL)-1H-BENZO(D)IMIDAZOL-2-YL)CARBAMATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
Code System Code Type Description
SMS_ID
100000087715
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
PUBCHEM
83969
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
EVMPD
SUB05296MIG
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
CHEBI
16959
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
FDA UNII
J39B52TV34
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
MESH
C027186
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
CAS
54029-12-8
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID4057768
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
NCI_THESAURUS
C72157
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
DRUG CENTRAL
104
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
MERCK INDEX
m1473
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB13871
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
INN
5979
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL1665
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY