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Albendazole S-oxide

Product NameAlbendazole S-oxide
CAS54029-12-8
MFC12H15N3O3S
MW281.33
EINECS628-805-8
MOL File54029-12-8.mol

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
Major Application	forensics and toxicology pharmaceutical (small molecule)
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)
InChIKey	VXTGHWHFYNYFFV-UHFFFAOYSA-N
SMILES	CCCS(=O)c1ccc2[nH]c(NC(=O)OC)nc2c1
CAS DataBase Reference	54029-12-8(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn
Risk Statements	22
Safety Statements	24/25
WGK Germany	3
RTECS	FD1080000
HS Code	29339900
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Repr. 2 Skin Sens. 1 STOT RE 2 Oral

Usage And Synthesis

Chemical Properties

White to Off-White Powder

Uses

Tubulin polymerization or assembled inhibitors

Uses

A metabolite of Albendazole, an anthelmintic

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

1,3-Bis(methoxycarbonyl)-2-methyl-2-thiopseudoeura

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

Preparation Products And Raw materials

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