albitiazolium   Click here for help

GtoPdb Ligand ID: 10407

Synonyms: SAR97276 | T3
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Albitiazolium was the clinical lead from the bisthiazolium series, a novel class of choline analogue with potent antimalarial activity [2-3].
We display the structure of the parent compound, with PubChem and ChEMBL links provided in the table below. However, the INN-assigned compound is in complex with bromide (represented in PubChem CID 11377022) and this compound is used in the experimental data listed under the 'biological activity' tab.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 104.7
Molecular weight 454.27
XLogP 6.8
No. Lipinski's rules broken 2
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Canonical SMILES OCCc1sc[n+](c1C)CCCCCCCCCCCC[n+]1csc(c1C)CCO
Isomeric SMILES OCCc1sc[n+](c1C)CCCCCCCCCCCC[n+]1csc(c1C)CCO
InChI InChI=1S/C24H42N2O2S2/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/q+2
1. Held J, Supan C, Salazar CLO, Tinto H, Bonkian LN, Nahum A, Sié A, Abdulla S, Cantalloube C, Djeriou E et al.. (2017)
Safety and efficacy of the choline analogue SAR97276 for malaria treatment: results of two phase 2, open-label, multicenter trials in African patients.
Malar. J., 16 (1): 188. [PMID:28472957]
2. Nicolas O, Margout D, Taudon N, Wein S, Calas M, Vial HJ, Bressolle FM. (2005)
Pharmacological properties of a new antimalarial bisthiazolium salt, T3, and a corresponding prodrug, TE3.
Antimicrob. Agents Chemother., 49 (9): 3631-9. [PMID:16127032]
3. Vial HJ, Wein S, Farenc C, Kocken C, Nicolas O, Ancelin ML, Bressolle F, Thomas A, Calas M. (2004)
Prodrugs of bisthiazolium salts are orally potent antimalarials.
Proc. Natl. Acad. Sci. U.S.A., 101 (43): 15458-63. [PMID:15492221]
4. Wein S, Maynadier M, Bordat Y, Perez J, Maheshwari S, Bette-Bobillo P, Tran Van Ba C, Penarete-Vargas D, Fraisse L, Cerdan R et al.. (2012)
Transport and pharmacodynamics of albitiazolium, an antimalarial drug candidate.
Br. J. Pharmacol., 166 (8): 2263-76. [PMID:22471905]