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)
Molecular Formula | C12H15N3O3S |
Molecular Weight | 281.331 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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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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[Efficacy of albendazole immunoliposome against echinococcosis granulosus in mice]. | 2001 |
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Albendazole sulphoxide enantiomeric ratios in plasma and target tissues after intravenous administration of ricobendazole to cattle. | 2001 Apr |
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Pharmacokinetics of ricobendazole in calves. | 2001 Jun |
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Effect of ruminal microflora on the biotransformation of netobimin, albendazole, albendazole sulfoxide, and albendazole sulfoxide enantiomers in an artificial rumen. | 2001 May |
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Enantioselective analysis of albendazole sulfoxide in cerebrospinal fluid by capillary electrophoresis. | 2001 Sep |
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Separation of albendazole sulfoxide enantiomers by chiral supercritical-fluid chromatography. | 2002 Dec 31 |
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Effect of grapefruit juice or cimetidine coadministration on albendazole bioavailability. | 2002 Mar |
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Laparoscopic treatment of hepatic hydatid cysts with a liposuction device. | 2002 Oct-Dec |
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Effect of clotrimazole on microsomal metabolism and pharmacokinetics of albendazole. | 2003 Jun |
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The co-administration of ivermectin and albendazole--safety, pharmacokinetics and efficacy against Onchocerca volvulus. | 2003 Mar |
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Aspects of the pharmacokinetics of albendazole sulphoxide in sheep. | 2003 Oct |
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Intestinal elimination of albendazole sulfoxide: pharmacokinetic effects of inhibitors. | 2003 Sep 16 |
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Secondary and primary murine alveolar echinococcosis: combined albendazole/nitazoxanide chemotherapy exhibits profound anti-parasitic activity. | 2004 Apr |
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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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Pharmacokinetic investigation of albendazole and praziquantel in Thai children infected with Giardia intestinalis. | 2004 Jun |
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Simultaneous determination of albendazole and its major active metabolite in human plasma using a sensitive and specific liquid chromatographic-tandem mass spectrometric method. | 2004 Jun 29 |
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[Influence of mobile phase composition on chiral separation of albendazole sulfoxide racemates]. | 2004 May |
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Enantioselective renal excretion of albendazole metabolites in patients with neurocysticercosis. | 2004 Oct |
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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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Inhibitory effect of albendazole and its metabolites on cytochromes P450 activities in rat and mouflon in vitro. | 2005 Jan-Feb |
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Transport of anthelmintic benzimidazole drugs by breast cancer resistance protein (BCRP/ABCG2). | 2005 May |
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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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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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Pharmacokinetics of albendazole sulfoxide enantiomers administered in racemic form and separately in rats. | 2008 Aug |
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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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Phase I biotransformation of albendazole in lancet fluke (Dicrocoelium dendriticum). | 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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Effect of age and gender in the pharmacokinetics of albendazole and albendazole sulphoxide enantiomers in goats. | 2009 Jun |
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Effect of ritonavir on the pharmacokinetics of the benzimidazoles albendazole and mebendazole: an interaction study in healthy volunteers. | 2009 Oct |
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
Substance Class |
Chemical
Created
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admin
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Fri Dec 15 16:12:26 GMT 2023
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on
Fri Dec 15 16:12:26 GMT 2023
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Record UNII |
J39B52TV34
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Record Status |
Validated (UNII)
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C250
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PARENT -> METABOLITE |
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PARENT -> IMPURITY |
sum of impurities B and C: maximum 0.4 percent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |