Albitiazolium bromide - CAS 321915-72-4
Catalog number: 321915-72-4
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C24H42Br2N2O2S2
Molecular Weight:
614.54
COA:
Inquire
Targets:
Others
Description:
Albitiazolium bromide is a choline analogue acts as a cholinergic receptor antagonists, inhibits choline transport into Plasmodium-infected erythrocytes, thus preventing parasite PC biosynthesis, and also to interact with plasmodial haemoglobin degradation in the food vacuole.
Purity:
≥95%
Appearance:
Solid powder
Synonyms:
SAR 97276; 1,12-bis[4-Methyl-5-(2-hydroxyethyl)thiazol-3-ium-3-yl]dodecane dibromide; 2-[3-[12-[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]dodecyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;dibromide;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
Cholinergic receptor antagonists
Quality Standard:
Enterprise standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Quantity:
Milligrams-Grams
InChIKey:
AFJCGBHHSKAACR-UHFFFAOYSA-L
InChI:
1S/C24H42N2O2S2.2BrH/c1-21-23(13-17-27)29-19-25(21)15-11-9-7-5-3-4-6-8-10-12-16-26-20-30-24(14-18-28)22(26)2;;/h19-20,27-28H,3-18H2,1-2H3;2*1H/q+2;;/p-2
Canonical SMILES:
CC1=C(SC=[N+]1CCCCCCCCCCCC[N+]2=CSC(=C2C)CCO)CCO.[Br-].[Br-]
Current Developer:
Sanofi-aventis
1.Antimalarial compounds in Phase II clinical development.
Held J;Jeyaraj S;Kreidenweiss A Expert Opin Investig Drugs. 2015 Mar;24(3):363-82. doi: 10.1517/13543784.2015.1000483. Epub 2015 Jan 7.
INTRODUCTION: ;Malaria is a major health problem in endemic countries and chemotherapy remains the most important tool in combating it. Treatment options are limited and essentially rely on a single drug class - the artemisinins. Efforts are ongoing to restrict the evolving threat of artemisinin resistance but declining sensitivity has been reported. Fueled by the ambitious aim of malaria eradication, novel antimalarial compounds, with improved properties, are now in the progressive phase of drug development.;AREAS COVERED: ;Herein, the authors describe antimalarial compounds currently in Phase II clinical development and present the results of these investigations.;EXPERT OPINION: ;Thanks to recent efforts, a number of promising antimalarial compounds are now in the pipeline. First safety data have been generated for all of these candidates, although their efficacy as antimalarials is still unclear for most of them. Of particular note are KAE609, KAF156 and DSM265, which are of chemical scaffolds new to malaria chemotherapy and would truly diversify antimalarial options. Apart from SAR97276, which also has a novel chemical scaffold that has had its development stopped, all other compounds in the pipeline belong to already known substance classes, which have been chemically modified.
2.Disulfide prodrugs of albitiazolium (T3/SAR97276): synthesis and biological activities.
Caldarelli SA;Hamel M;Duckert JF;Ouattara M;Calas M;Maynadier M;Wein S;Périgaud C;Pellet A;Vial HJ;Peyrottes S J Med Chem. 2012 May 24;55(10):4619-28. doi: 10.1021/jm3000328. Epub 2012 May 16.
We report herein the design, synthesis, and biological screening of a series of 15 disulfide prodrugs as precursors of albitiazolium bromide (T3/SAR97276, compound 1), a choline analogue which is currently being evaluated in clinical trials (phase II) for severe malaria. The corresponding prodrugs are expected to revert back to the active bis-thiazolium salt through an enzymatic reduction of the disulfide bond. To enhance aqueous solubility of these prodrugs, an amino acid residue (valine or lysine) or a phosphate group was introduced on the thiazolium side chain. Most of the novel derivatives exhibited potent in vitro antimalarial activity against P. falciparum. After oral administration, the cyclic disulfide prodrug 8 showed the best improvement of oral efficacy in comparison to the parent drug.
3.Quantitation of SAR97276 in mouse tissues by rapid resolution liquid chromatography-mass spectrometry.
Margout D;Wein S;Gandon H;Gattacceca F;Vial HJ;Bressolle FM J Sep Sci. 2009 Jun;32(11):1808-15. doi: 10.1002/jssc.200900059.
1,12-Bis[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium]dodecane dibromide (SAR97276, T3) is a new antimalarial drug, which is currently being evaluated in clinical trials for severe malaria. Drug accumulation inside the parasite and a dual mechanism of action are a major strength of this compound, as it could help delay the development of resistance. The purpose of this article was to develop a rapid resolution LC-MS method for quantifying SAR97276 in mouse tissues. The LC system consisted of Zorbax Eclipse XDB C8 (1.8 microm, 50 x 4.6 mm, 60 degrees C) column. Elution with a gradient mobile phase consisting of ACN-trimethylamine-formate buffer (pH 3) at a flow rate of 1 mL/min yielded sharp, utmost-resolved peaks within 2 min. Tissue samples were powdered under liquid nitrogen. After protein precipitation with citric acid, SPE using WCX cartridges was used for sample preparation. There was no influence of the matrix on the detection of either SAR97276 or the IS. Assay precision was <13% and accuracy was 90-107%. The lower LOQs were 3.3 microg/kg in brain and 33 microg/kg in liver and heart. This newly developed method was used to study the tissue distribution of SAR97276 in mouse as part of the ongoing development of SAR97276.
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CAS 321915-72-4 Albitiazolium bromide

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