Albendazole S-oxide
Albendazole S-oxide Basic information
- Product Name:
- Albendazole S-oxide
- Synonyms:
-
- Albendazole Sulphoxide HCL
- methyl n-(6-propylsulfinyl-1h-benzoimidazol-2-yl)carbamate
- Albendazole EP Impurity B-d7
- Albendazole Impurity 2（Albendazole EP Impurity B）
- Methyl [5-(propylsulfinyl)-1Hbenzimidazol-2-yl]carbamate
- Albendazole-EP-Imp-B
- RS-8852
- RICOBENDAZOLE
- CAS:
- 54029-12-8
- MF:
- C12H15N3O3S
- MW:
- 281.33
- EINECS:
- 628-805-8
- Product Categories:
-
- Veterinary drugs
- Inhibitors
- Metabolites & Impurites
- Animal Pharmaceuticals
- Various Metabolites and Impurities
- Intermediates & Fine Chemicals
- Metabolites
- Pharmaceuticals
- Mol File:
- 54029-12-8.mol
Albendazole S-oxide Chemical Properties
- Melting point:
- 226-228°C dec.
- Density
- 1.40
- storage temp.
- Sealed in dry,2-8°C
- solubility
- Chloroform (Slightly, Heated), Methanol (Slightly)
- form
- Solid
- pka
- pKa 3.28±0.01(H2O t=25.0±0.1 I=0.1(NaCl))(Approximate); 9.93±0.01(H2O t=25.0±0.1 I=0.1(NaCl))(Approximate)
- color
- colorless or white
- Water Solubility
- 62mg/L(25 ºC)
- BRN
- 677664
- InChIKey
- VXTGHWHFYNYFFV-UHFFFAOYSA-N
- CAS DataBase Reference
- 54029-12-8(CAS DataBase Reference)
Albendazole S-oxide Usage And Synthesis
Chemical Properties
White to Off-White Powder
Uses
A metabolite of Albendazole, an anthelmintic
Uses
Tubulin polymerization or assembled inhibitors
Definition
ChEBI: Albendazole S-oxide is a sulfoxide. It is functionally related to an albendazole.
Biological Activity
Ricobendazole is a key metabolite of albendazole and acts as an anthelmintic. It has been shown to induce apoptosis in human cancer cell line HT-29, possibly by arresting cell cycle at the G2/M phase.
Synthesis
34840-23-8
66868-66-4
54029-12-8
3.56 g (18 mmol) of 4-(1-propylsulfinyl)-1,2-diaminobenzene was dissolved in 45 mL of methanol and 1.03 mL of acetic acid and 3.84 g (19.8 mmol) of 1,3-bis(methoxycarbonyl)-S-methylisothiourea were added. The reaction mixture was heated to reflux for 2.5 hours, followed by cooling and removing the solvent under reduced pressure. The resulting white solid was digested with water, filtered, washed with ether and dried to give 4.1 g of white solid product, albendazole sulfoxide, with a melting point of 205°C to 216°C and a yield of 81%.
in vivo
Albendazole sulfoxide (0.5 mg/kg, i.m., BID, 15 days) reduces cyst size and weight in Balb/c mice infected with protoscoleces[3].
References
[1] Patent: US4076825, 1978, A
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