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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
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
In vitro ruminal biotransformation of benzimidazole sulphoxide anthelmintics: enantioselective sulphoreduction in sheep and cattle.
2002 Feb
Effect of grapefruit juice or cimetidine coadministration on albendazole bioavailability.
2002 Mar
Placental transfer of albendazole sulphoxide enantiomers in sheep.
2002 Mar
Metabolism and residue depletion of albendazole and its metabolites in rainbow trout, tilapia and Atlantic salmon after oral administration.
2003 Dec
Effect of two formulations of benzimidazole carbamates on the viability of cysts of Echinococcus granulosus in vivo.
2003 Dec
Simultaneous liquid chromatography-tandem mass spectrometric determination of albendazole sulfoxide and albendazole sulfone in plasma.
2003 Jan 5
Placental and fetal toxicity of albendazole sulphoxide in Wistar rats.
2003 Jun
Therapy for neurocysticercosis.
2004 Jan
Albendazole sulphoxide concentrations in plasma of endemic normals from a lymphatic filariasis endemic region using liquid chromatography.
2004 Jan 25
Inhibitory effect of albendazole and its metabolites on cytochromes P450 activities in rat and mouflon in vitro.
2005 Jan-Feb
Death related to albendazole-induced pancytopenia: case report and review.
2005 Mar
Antitumor activity of albendazole against the human colorectal cancer cell line HT-29: in vitro and in a xenograft model of peritoneal carcinomatosis.
2005 May
An in vitro kinetic method for detection of precipitation of poorly soluble drugs.
2005 Nov 4
Role of ABC transporters in veterinary drug research and parasite resistance.
2006 Apr
Albendazole trial at 15 or 30 mg/kg/day for subarachnoid and intraventricular cysticercosis.
2006 Feb 14
Efficacy of nitazoxanide, tizoxanide and tizoxanide/albendazole sulphoxide combination against Taenia crassiceps cysts.
2007 Feb
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
Synthesis and in vitro cysticidal activity of new benzimidazole derivatives.
2009 Apr
Use of albendazole sulfoxide, albendazole sulfone, and combined solutions as scolicidal agents on hydatid cysts (in vitro study).
2009 Jan 7
Stability of ricobendazole in aqueous solutions.
2009 Jul 12
Diagnostic problems with parasitic and non-parasitic splenic cysts.
2009 May 29
Comparative in vitro effect of artemether and albendazole on adult Toxocara canis.
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 UTC 2023
Edited
by admin
on Fri Dec 15 16:12:26 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 Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
Code System Code Type Description
SMS_ID
100000087715
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
PUBCHEM
83969
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
EVMPD
SUB05296MIG
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
CHEBI
16959
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
FDA UNII
J39B52TV34
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
MESH
C027186
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
CAS
54029-12-8
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID4057768
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
NCI_THESAURUS
C72157
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
DRUG CENTRAL
104
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
MERCK INDEX
m1473
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB13871
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
INN
5979
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL1665
Created by admin on Fri Dec 15 16:12:26 UTC 2023 , Edited by admin on Fri Dec 15 16:12:26 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