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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
Albendazole sulphoxide enantiomeric ratios in plasma and target tissues after intravenous administration of ricobendazole to cattle.
2001 Apr
Pharmacokinetics of ricobendazole in calves.
2001 Jun
Effect of ruminal microflora on the biotransformation of netobimin, albendazole, albendazole sulfoxide, and albendazole sulfoxide enantiomers in an artificial rumen.
2001 May
Enantioselective analysis of albendazole sulfoxide in cerebrospinal fluid by capillary electrophoresis.
2001 Sep
Separation of albendazole sulfoxide enantiomers by chiral supercritical-fluid chromatography.
2002 Dec 31
Effect of grapefruit juice or cimetidine coadministration on albendazole bioavailability.
2002 Mar
Laparoscopic treatment of hepatic hydatid cysts with a liposuction device.
2002 Oct-Dec
Effect of clotrimazole on microsomal metabolism and pharmacokinetics of albendazole.
2003 Jun
The co-administration of ivermectin and albendazole--safety, pharmacokinetics and efficacy against Onchocerca volvulus.
2003 Mar
Aspects of the pharmacokinetics of albendazole sulphoxide in sheep.
2003 Oct
Intestinal elimination of albendazole sulfoxide: pharmacokinetic effects of inhibitors.
2003 Sep 16
Secondary and primary murine alveolar echinococcosis: combined albendazole/nitazoxanide chemotherapy exhibits profound anti-parasitic activity.
2004 Apr
Resistance to benzimidazole and macrocyclic lactone anthelmintics in cattle nematodes in Argentina.
2004 Aug 6
A possible model of benzimidazole binding to beta-tubulin disclosed by invoking an inter-domain movement.
2004 Dec
Pharmacokinetic investigation of albendazole and praziquantel in Thai children infected with Giardia intestinalis.
2004 Jun
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
[Influence of mobile phase composition on chiral separation of albendazole sulfoxide racemates].
2004 May
Enantioselective renal excretion of albendazole metabolites in patients with neurocysticercosis.
2004 Oct
Quantitative determination of albendazole metabolites in sheep spermatozoa and seminal plasma by liquid chromatographic analysis with fluorescence detection.
2004 Sep 3
Liver microsomal biotransformation of albendazole in deer, cattle, sheep and pig and some related wild breeds.
2005 Aug
Inhibitory effect of albendazole and its metabolites on cytochromes P450 activities in rat and mouflon in vitro.
2005 Jan-Feb
Transport of anthelmintic benzimidazole drugs by breast cancer resistance protein (BCRP/ABCG2).
2005 May
Development and optimization of a rapid HPLC method for analysis of ricobendazole and albendazole sulfone in sheep plasma.
2005 Sep 1
Albendazole trial at 15 or 30 mg/kg/day for subarachnoid and intraventricular cysticercosis.
2006 Feb 14
Enantiomeric separation of chiral sulfoxides by supercritical fluid chromatography.
2006 Jul
Evaluation of the efficacy of albendazole sulphoxide and praziquantel in combination on Taenia crassiceps cysts: in vitro studies.
2006 Mar
Pharmacokinetics of albendazole sulfoxide enantiomers administered in racemic form and separately in rats.
2008 Aug
Albendazole versus praziquantel in the treatment of neurocysticercosis: a meta-analysis of comparative trials.
2008 Mar 12
Phase I biotransformation of albendazole in lancet fluke (Dicrocoelium dendriticum).
2009 Feb
Use of albendazole sulfoxide, albendazole sulfone, and combined solutions as scolicidal agents on hydatid cysts (in vitro study).
2009 Jan 7
Effect of age and gender in the pharmacokinetics of albendazole and albendazole sulphoxide enantiomers in goats.
2009 Jun
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
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 Fri Dec 15 16:12:26 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:26 GMT 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 Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
Code System Code Type Description
SMS_ID
100000087715
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
PUBCHEM
83969
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
EVMPD
SUB05296MIG
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
CHEBI
16959
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
FDA UNII
J39B52TV34
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
MESH
C027186
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
CAS
54029-12-8
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID4057768
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
NCI_THESAURUS
C72157
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
DRUG CENTRAL
104
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
MERCK INDEX
m1473
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB13871
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
INN
5979
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL1665
Created by admin on Fri Dec 15 16:12:26 GMT 2023 , Edited by admin on Fri Dec 15 16:12:26 GMT 2023
PRIMARY
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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