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
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)
DescriptionSources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500009687.pdfCurator'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
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500009687.pdf
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL384 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15565325 |
2.35 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | RICAZOL Approved UseRicazol 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
Title | Date | PubMed |
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Resistance to benzimidazole and macrocyclic lactone anthelmintics in cattle nematodes in Argentina. | 2004 Aug 6 |
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A possible model of benzimidazole binding to beta-tubulin disclosed by invoking an inter-domain movement. | 2004 Dec |
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Therapy for neurocysticercosis. | 2004 Jan |
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[Influence of mobile phase composition on chiral separation of albendazole sulfoxide racemates]. | 2004 May |
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Quantitative determination of albendazole metabolites in sheep spermatozoa and seminal plasma by liquid chromatographic analysis with fluorescence detection. | 2004 Sep 3 |
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Liver microsomal biotransformation of albendazole in deer, cattle, sheep and pig and some related wild breeds. | 2005 Aug |
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Analytical and semipreparative resolution of enatiomers of albendazole sulfoxide by HPLC on amylose tris (3,5-dimethylphenylcarbamate) chiral stationary phases. | 2005 Jan 31 |
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Inhibitory effect of albendazole and its metabolites on cytochromes P450 activities in rat and mouflon in vitro. | 2005 Jan-Feb |
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Preoperative albendazole and scolices viability in patients with hepatic echinococcosis. | 2005 Jun |
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Death related to albendazole-induced pancytopenia: case report and review. | 2005 Mar |
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Physicochemical characterization of ricobendazole: I. Solubility, lipophilicity, and ionization characteristics. | 2005 May |
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Transport of anthelmintic benzimidazole drugs by breast cancer resistance protein (BCRP/ABCG2). | 2005 May |
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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 |
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An in vitro kinetic method for detection of precipitation of poorly soluble drugs. | 2005 Nov 4 |
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Pharmacokinetics of ricobendazole after its intravenous, intraruminal and subcutaneous administration in sheep. | 2005 Oct |
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Development and optimization of a rapid HPLC method for analysis of ricobendazole and albendazole sulfone in sheep plasma. | 2005 Sep 1 |
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Role of ABC transporters in veterinary drug research and parasite resistance. | 2006 Apr |
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Assessments of pharmacokinetic drug interactions and tolerability of albendazole, praziquantel and ivermectin combinations. | 2006 Apr |
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Interaction of enrofloxacin with breast cancer resistance protein (BCRP/ABCG2): influence of flavonoids and role in milk secretion in sheep. | 2006 Aug |
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Variation among faecal egg counts following natural nematode infection in Scottish Blackface lambs. | 2006 Feb |
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Albendazole trial at 15 or 30 mg/kg/day for subarachnoid and intraventricular cysticercosis. | 2006 Feb 14 |
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Enantiomeric separation of chiral sulfoxides by supercritical fluid chromatography. | 2006 Jul |
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Evaluation of the efficacy of albendazole sulphoxide and praziquantel in combination on Taenia crassiceps cysts: in vitro studies. | 2006 Mar |
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A dual anthelmintic treatment strategic scheme for the control of fasciolosis in dairy sheep farms. | 2006 Nov |
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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 |
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Pharmacokinetics of albendazole in New Zealand white rabbits: oral versus intraperitoneal administration. | 2007 Jan-Feb |
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Simultaneous determination of albendazole metabolites, praziquantel and its metabolite in plasma by high-performance liquid chromatography-electrospray mass spectrometry. | 2007 Jun 28 |
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Absorption and metabolism of albendazole after intestinal ischemia/reperfusion. | 2007 May |
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Pharmacokinetics of albendazole sulfoxide enantiomers administered in racemic form and separately in rats. | 2008 Aug |
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[In vitro observation on albendazole sulfoxide and its enantiomers against Echinococcus granulosus protoscolex]. | 2008 Dec 30 |
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Determination of albendazole metabolites by direct injection of bovine plasma and multidimensional achiral-chiral high performance liquid chromatography. | 2008 Jun 30 |
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Kinetic disposition of albendazole in goats subclinically infected with gastrointestinal nematodes vis-à-vis naive animals following oral and intraruminal administration. | 2008 Mar |
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Albendazole versus praziquantel in the treatment of neurocysticercosis: a meta-analysis of comparative trials. | 2008 Mar 12 |
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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 |
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LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus. | 2008 May |
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Diagnosis and treatment of pulmonary cystic hydatidosis. | 2008 Oct |
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Characterization of substrates and inhibitors for the in vitro assessment of Bcrp mediated drug-drug interactions. | 2008 Oct |
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Synthesis and in vitro cysticidal activity of new benzimidazole derivatives. | 2009 Apr |
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Albendazole enantiomeric metabolism and binding to cytosolic proteins in the liver fluke Fasciola hepatica. | 2009 Feb |
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Use of albendazole sulfoxide, albendazole sulfone, and combined solutions as scolicidal agents on hydatid cysts (in vitro study). | 2009 Jan 7 |
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Stability of ricobendazole in aqueous solutions. | 2009 Jul 12 |
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Pharmacological assessment of netobimin as a potential anthelmintic for use in horses: plasma disposition, faecal excretion and efficacy. | 2009 Jun |
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Effect of age and gender in the pharmacokinetics of albendazole and albendazole sulphoxide enantiomers in goats. | 2009 Jun |
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Diagnostic problems with parasitic and non-parasitic splenic cysts. | 2009 May 29 |
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Residue depletion of albendazole and its metabolites in the muscle tissue of large mouth and hybrid striped bass after oral administration. | 2009 Nov 13 |
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Effect of ritonavir on the pharmacokinetics of the benzimidazoles albendazole and mebendazole: an interaction study in healthy volunteers. | 2009 Oct |
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Comparative in vitro effect of artemether and albendazole on adult Toxocara canis. | 2009 Oct |
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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
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500009687.pdf
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15565325
Albendazole oxide inhibited human cancer cell line HT-29 with IC50 2.35 uM
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NCI_THESAURUS |
C250
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ACTIVE MOIETY
PARENT (METABOLITE)