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MedKoo Cat#: 319819 | Name: Albitiazolium bromide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Albitiazolium bromide, also known as SAR 97276, is a choline analogue which is currently being evaluated in clinical trials (phase II) for severe malaria. Albitiazolium bromide inhibits choline transport into Plasmodium-infected erythrocytes, thus preventing parasite PC biosynthesis, and also to interact with plasmodial haemoglobin degradation in the food vacuole.

Chemical Structure

Albitiazolium bromide
Albitiazolium bromide
CAS#321915-72-4 (bromide)

Theoretical Analysis

MedKoo Cat#: 319819

Name: Albitiazolium bromide

CAS#: 321915-72-4 (bromide)

Chemical Formula: C24H42Br2N2O2S2

Exact Mass:

Molecular Weight: 614.54

Elemental Analysis: C, 46.91; H, 6.89; Br, 26.00; N, 4.56; O, 5.21; S, 10.43

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
753439-46-2 (cation) 321915-72-4 (bromide)
Synonym
SAR97276; SAR-97276; SAR 97276; Albitiazolium bromide
IUPAC/Chemical Name
3,3'-(dodecane-1,12-diyl)bis(5-(2-hydroxyethyl)-4-methylthiazol-3-ium) bromide
InChi Key
AFJCGBHHSKAACR-UHFFFAOYSA-L
InChi Code
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
SMILES Code
CC1=C(CCO)SC=[N+]1CCCCCCCCCCCC[N+]2=CSC(CCO)=C2C.[Br-].[Br-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 614.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Penarete-Vargas DM, Boisson A, Urbach S, Chantelauze H, Peyrottes S, Fraisse L, Vial HJ. A chemical proteomics approach for the search of pharmacological targets of the antimalarial clinical candidate albitiazolium in Plasmodium falciparum using photocrosslinking and click chemistry. PLoS One. 2014 Dec 3;9(12):e113918. doi: 10.1371/journal.pone.0113918. eCollection 2014. PubMed PMID: 25470252; PubMed Central PMCID: PMC4254740. 2: Peyrottes S, Caldarelli S, Wein S, Perigaud C, Vial H. Exploring prodrug approaches for albitiazolium and its analogues. Curr Top Med Chem. 2014;14(14):1653-67. PubMed PMID: 25116583. 3: Wein S, Tran Van Ba C, Maynadier M, Bordat Y, Perez J, Peyrottes S, Fraisse L, Vial HJ. New insight into the mechanism of accumulation and intraerythrocytic compartmentation of albitiazolium, a new type of antimalarial. Antimicrob Agents Chemother. 2014 Sep;58(9):5519-27. doi: 10.1128/AAC.00040-14. Epub 2014 Jul 7. PubMed PMID: 25001307; PubMed Central PMCID: PMC4135818. 4: Caldarelli SA, Hamel M, Duckert JF, Ouattara M, Calas M, Maynadier M, Wein S, Périgaud C, Pellet A, Vial HJ, Peyrottes S. Disulfide prodrugs of albitiazolium (T3/SAR97276): synthesis and biological activities. J Med Chem. 2012 May 24;55(10):4619-28. doi: 10.1021/jm3000328. Epub 2012 May 16. PubMed PMID: 22591034. 5: Wein S, Maynadier M, Bordat Y, Perez J, Maheshwari S, Bette-Bobillo P, Tran Van Ba C, Penarete-Vargas D, Fraisse L, Cerdan R, Vial H. Transport and pharmacodynamics of albitiazolium, an antimalarial drug candidate. Br J Pharmacol. 2012 Aug;166(8):2263-76. doi: 10.1111/j.1476-5381.2012.01966.x. PubMed PMID: 22471905; PubMed Central PMCID: PMC3437492. 6: Alberge B, Gannoun-Zaki L, Bascunana C, Tran van Ba C, Vial H, Cerdan R. Comparison of the cellular and biochemical properties of Plasmodium falciparum choline and ethanolamine kinases. Biochem J. 2009 Dec 14;425(1):149-58. doi: 10.1042/BJ20091119. PubMed PMID: 19845508. 7: Margout D, Wein S, Gandon H, Gattacceca F, Vial HJ, Bressolle FM. Quantitation of SAR97276 in mouse tissues by rapid resolution liquid chromatography-mass spectrometry. J Sep Sci. 2009 Jun;32(11):1808-15. doi: 10.1002/jssc.200900059. PubMed PMID: 19479768. 8: Margout D, Bontemps N, Kocken CH, Vial HJ, Bressolle FM. Rapid resolution liquid chromatography-mass spectrometry determination of SAR97276 in monkey matrices. Pharmacokinetics in rhesus monkey infected by Plasmodium cynomolgi. J Pharm Biomed Anal. 2009 Jul 12;49(5):1266-71. doi: 10.1016/j.jpba.2009.02.019. Epub 2009 Feb 27. PubMed PMID: 19303732. 9: Taudon N, Margout D, Wein S, Calas M, Vial HJ, Bressolle FM. Quantitative analysis of a bis-thiazolium antimalarial compound, SAR97276, in mouse plasma and red blood cell samples, using liquid chromatography mass spectrometry. J Pharm Biomed Anal. 2008 Jan 7;46(1):148-56. Epub 2007 Oct 13. PubMed PMID: 18023551. 10: Nicolas O, Margout D, Taudon N, Wein S, Calas M, Vial HJ, Bressolle FM. Pharmacological properties of a new antimalarial bisthiazolium salt, T3, and a corresponding prodrug, TE3. Antimicrob Agents Chemother. 2005 Sep;49(9):3631-9. PubMed PMID: 16127032; PubMed Central PMCID: PMC1195427. 11: Nicolas O, Margout D, Taudon N, Calas M, Vial HJ, Bressolle F. Liquid chromatography-electrospray mass spectrometry determination of a bis-thiazolium compound with potent antimalarial activity and its neutral bioprecursor in human plasma, whole blood and red blood cells. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):83-93. Epub 2005 Apr 19. PubMed PMID: 15866496. 12: Nicolas O, Farenc C, Calas M, Vial HJ, Bressolle F. Quantification of antimalarial bisthiazolium compounds and their neutral bioprecursors in plasma by liquid chromatography-electrospray mass spectrometry. Clin Chem. 2005 Mar;51(3):593-602. Epub 2005 Jan 6. PubMed PMID: 15637133.