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=CC2=C(NC(NC(=O)OC)=N2)C=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 |
|---|---|---|
| Residue depletion of albendazole and its metabolites in the muscle tissue of large mouth and hybrid striped bass after oral administration. | 2009-11-13 |
|
| Effect of ritonavir on the pharmacokinetics of the benzimidazoles albendazole and mebendazole: an interaction study in healthy volunteers. | 2009-10 |
|
| Comparative in vitro effect of artemether and albendazole on adult Toxocara canis. | 2009-10 |
|
| Liquid chromatography/mass spectrometric identification of benzimidazole anthelminthics metabolites formed ex vivo by Dicrocoelium dendriticum. | 2009-09 |
|
| Enantiomeric behaviour of albendazole and fenbendazole sulfoxides in domestic animals: pharmacological implications. | 2009-09 |
|
| Stability of ricobendazole in aqueous solutions. | 2009-07-12 |
|
| Pharmacological assessment of netobimin as a potential anthelmintic for use in horses: plasma disposition, faecal excretion and efficacy. | 2009-06 |
|
| Effect of age and gender in the pharmacokinetics of albendazole and albendazole sulphoxide enantiomers in goats. | 2009-06 |
|
| Diagnostic problems with parasitic and non-parasitic splenic cysts. | 2009-05-29 |
|
| Synthesis and in vitro cysticidal activity of new benzimidazole derivatives. | 2009-04 |
|
| Albendazole enantiomeric metabolism and binding to cytosolic proteins in the liver fluke Fasciola hepatica. | 2009-02 |
|
| Phase I biotransformation of albendazole in lancet fluke (Dicrocoelium dendriticum). | 2009-02 |
|
| Use of albendazole sulfoxide, albendazole sulfone, and combined solutions as scolicidal agents on hydatid cysts (in vitro study). | 2009-01-07 |
|
| [In vitro observation on albendazole sulfoxide and its enantiomers against Echinococcus granulosus protoscolex]. | 2008-12-30 |
|
| Diagnosis and treatment of pulmonary cystic hydatidosis. | 2008-10 |
|
| Characterization of substrates and inhibitors for the in vitro assessment of Bcrp mediated drug-drug interactions. | 2008-10 |
|
| Pharmacokinetics of albendazole sulfoxide enantiomers administered in racemic form and separately in rats. | 2008-08 |
|
| Determination of albendazole metabolites by direct injection of bovine plasma and multidimensional achiral-chiral high performance liquid chromatography. | 2008-06-30 |
|
| Determination of albendazole and its metabolites in the muscle tissue of hybrid striped and largemouth bass using liquid chromatography with fluorescence detection. | 2008-05-15 |
|
| LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus. | 2008-05 |
|
| Albendazole versus praziquantel in the treatment of neurocysticercosis: a meta-analysis of comparative trials. | 2008-03-12 |
|
| Kinetic disposition of albendazole in goats subclinically infected with gastrointestinal nematodes vis-à-vis naive animals following oral and intraruminal administration. | 2008-03 |
|
| Simultaneous determination of albendazole metabolites, praziquantel and its metabolite in plasma by high-performance liquid chromatography-electrospray mass spectrometry. | 2007-06-28 |
|
| Absorption and metabolism of albendazole after intestinal ischemia/reperfusion. | 2007-05 |
|
| Pharmacokinetics of albendazole in New Zealand white rabbits: oral versus intraperitoneal administration. | 2007-03-14 |
|
| Efficacy of nitazoxanide, tizoxanide and tizoxanide/albendazole sulphoxide combination against Taenia crassiceps cysts. | 2007-02 |
|
| A dual anthelmintic treatment strategic scheme for the control of fasciolosis in dairy sheep farms. | 2006-11 |
|
| Plasma disposition and faecal excretion of netobimin metabolites and enantiospecific disposition of albendazole sulphoxide produced in ewes. | 2006-10 |
|
| Interaction of enrofloxacin with breast cancer resistance protein (BCRP/ABCG2): influence of flavonoids and role in milk secretion in sheep. | 2006-08 |
|
| Enantiomeric separation of chiral sulfoxides by supercritical fluid chromatography. | 2006-07 |
|
| Role of ABC transporters in veterinary drug research and parasite resistance. | 2006-04 |
|
| Assessments of pharmacokinetic drug interactions and tolerability of albendazole, praziquantel and ivermectin combinations. | 2006-04 |
|
| Evaluation of the efficacy of albendazole sulphoxide and praziquantel in combination on Taenia crassiceps cysts: in vitro studies. | 2006-03 |
|
| Albendazole trial at 15 or 30 mg/kg/day for subarachnoid and intraventricular cysticercosis. | 2006-02-14 |
|
| Variation among faecal egg counts following natural nematode infection in Scottish Blackface lambs. | 2006-02 |
|
| An in vitro kinetic method for detection of precipitation of poorly soluble drugs. | 2005-11-04 |
|
| Pharmacokinetics of ricobendazole after its intravenous, intraruminal and subcutaneous administration in sheep. | 2005-10 |
|
| Development and optimization of a rapid HPLC method for analysis of ricobendazole and albendazole sulfone in sheep plasma. | 2005-09-01 |
|
| Liver microsomal biotransformation of albendazole in deer, cattle, sheep and pig and some related wild breeds. | 2005-08 |
|
| Preoperative albendazole and scolices viability in patients with hepatic echinococcosis. | 2005-06 |
|
| Physicochemical characterization of ricobendazole: I. Solubility, lipophilicity, and ionization characteristics. | 2005-05 |
|
| Transport of anthelmintic benzimidazole drugs by breast cancer resistance protein (BCRP/ABCG2). | 2005-05 |
|
| Antitumor activity of albendazole against the human colorectal cancer cell line HT-29: in vitro and in a xenograft model of peritoneal carcinomatosis. | 2005-05 |
|
| Death related to albendazole-induced pancytopenia: case report and review. | 2005-03 |
|
| Highly sensitive ion pair liquid chromatographic determination of albendazole marker residue in animal tissues. | 2005-02-23 |
|
| Analytical and semipreparative resolution of enatiomers of albendazole sulfoxide by HPLC on amylose tris (3,5-dimethylphenylcarbamate) chiral stationary phases. | 2005-01-31 |
|
| A possible model of benzimidazole binding to beta-tubulin disclosed by invoking an inter-domain movement. | 2004-12 |
|
| Inhibitory effect of albendazole and its metabolites on cytochromes P450 activities in rat and mouflon in vitro. | 2004-05-10 |
|
| [Influence of mobile phase composition on chiral separation of albendazole sulfoxide racemates]. | 2004-05 |
|
| Therapy for neurocysticercosis. | 2004-01 |
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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Edited
Mon Mar 31 18:21:49 GMT 2025
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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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| Cmax | PHARMACOKINETIC |
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