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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

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

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
[Efficacy of albendazole immunoliposome against echinococcosis granulosus in mice].
2001
Separation of albendazole sulfoxide enantiomers by chiral supercritical-fluid chromatography.
2002 Dec 31
In vitro ruminal biotransformation of benzimidazole sulphoxide anthelmintics: enantioselective sulphoreduction in sheep and cattle.
2002 Feb
Enantioselective binding of albendazole sulphoxide to cytosolic proteins from helminth parasites.
2002 Jan-Feb
Metabolism and residue depletion of albendazole and its metabolites in rainbow trout, tilapia and Atlantic salmon after oral administration.
2003 Dec
The effects of albendazole and its metabolites on hepatic cytochromes P450 activities in mouflon and rat.
2003 Dec
Simultaneous liquid chromatography-tandem mass spectrometric determination of albendazole sulfoxide and albendazole sulfone in plasma.
2003 Jan 5
Transtegumental diffusion of benzimidazole anthelmintics into Moniezia benedeni: correlation with their octanol-water partition coefficients.
2003 Jan-Feb
Placental and fetal toxicity of albendazole sulphoxide in Wistar rats.
2003 Jun
Analysis of albendazole metabolites by electrospray LC-MS/MS as a probe to elucidate electro-oxidation mechanism of albendazole.
2003 Jun 1
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
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
The effect of solubilization on the oral bioavailability of three benzimidazole carbamate drugs.
2004 Mar 19
Effect of the ionophore antibiotic monensin on the ruminal biotransformation of benzimidazole anthelmintics.
2004 May
Highly sensitive ion pair liquid chromatographic determination of albendazole marker residue in animal tissues.
2005 Feb 23
Preoperative albendazole and scolices viability in patients with hepatic echinococcosis.
2005 Jun
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
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
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
Characterization of substrates and inhibitors for the in vitro assessment of Bcrp mediated drug-drug interactions.
2008 Oct
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
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
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:39:54 UTC 2023
Edited
by admin
on Wed Jul 05 23:39:54 UTC 2023
Record UNII
J39B52TV34
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
Code System Code Type Description
SMS_ID
100000087715
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
PUBCHEM
83969
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
EVMPD
SUB05296MIG
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
CHEBI
16959
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
FDA UNII
J39B52TV34
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
MESH
C027186
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
CAS
54029-12-8
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID4057768
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
NCI_THESAURUS
C72157
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
DRUG CENTRAL
104
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
MERCK INDEX
M1473
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB13871
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
INN
5979
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL1665
Created by admin on Wed Jul 05 23:39:55 UTC 2023 , Edited by admin on Wed Jul 05 23:39:55 UTC 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
LIGAND->BINDER
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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