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 |
---|---|---|---|
Target ID: CHEMBL384 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15565325 |
2.35 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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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Separation of albendazole sulfoxide enantiomers by chiral supercritical-fluid chromatography. | 2002 Dec 31 |
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In vitro ruminal biotransformation of benzimidazole sulphoxide anthelmintics: enantioselective sulphoreduction in sheep and cattle. | 2002 Feb |
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Enantioselective binding of albendazole sulphoxide to cytosolic proteins from helminth parasites. | 2002 Jan-Feb |
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Metabolism and residue depletion of albendazole and its metabolites in rainbow trout, tilapia and Atlantic salmon after oral administration. | 2003 Dec |
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The effects of albendazole and its metabolites on hepatic cytochromes P450 activities in mouflon and rat. | 2003 Dec |
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Simultaneous liquid chromatography-tandem mass spectrometric determination of albendazole sulfoxide and albendazole sulfone in plasma. | 2003 Jan 5 |
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Transtegumental diffusion of benzimidazole anthelmintics into Moniezia benedeni: correlation with their octanol-water partition coefficients. | 2003 Jan-Feb |
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Placental and fetal toxicity of albendazole sulphoxide in Wistar rats. | 2003 Jun |
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Analysis of albendazole metabolites by electrospray LC-MS/MS as a probe to elucidate electro-oxidation mechanism of albendazole. | 2003 Jun 1 |
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Use of semipreparative supercritical fluid chromatography to obtain small quantities of the albendazole sulfoxide enantiomers. | 2003 Sep 5 |
|
Secondary and primary murine alveolar echinococcosis: combined albendazole/nitazoxanide chemotherapy exhibits profound anti-parasitic activity. | 2004 Apr |
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Reversed-phase liquid chromatographic method with fluorescence detection for the simultaneous determination of albendazole sulphoxide, albendazole sulphone and albendazole 2-aminosulphone in sheep plasma. | 2004 Jun 15 |
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The effect of solubilization on the oral bioavailability of three benzimidazole carbamate drugs. | 2004 Mar 19 |
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Effect of the ionophore antibiotic monensin on the ruminal biotransformation of benzimidazole anthelmintics. | 2004 May |
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Highly sensitive ion pair liquid chromatographic determination of albendazole marker residue in animal tissues. | 2005 Feb 23 |
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Preoperative albendazole and scolices viability in patients with hepatic echinococcosis. | 2005 Jun |
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Physicochemical characterization of ricobendazole: I. Solubility, lipophilicity, and ionization characteristics. | 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 |
|
Variation among faecal egg counts following natural nematode infection in Scottish Blackface lambs. | 2006 Feb |
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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 |
|
Efficacy of nitazoxanide, tizoxanide and tizoxanide/albendazole sulphoxide combination against Taenia crassiceps cysts. | 2007 Feb |
|
[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 |
|
LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus. | 2008 May |
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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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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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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
Substance Class |
Chemical
Created
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admin
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Edited
Wed Jul 05 23:39:54 UTC 2023
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Wed Jul 05 23:39:54 UTC 2023
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Record UNII |
J39B52TV34
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Validated (UNII)
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C250
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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 |