ALBITIAZOLIUM BROMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H42N2O2S2.2Br
Molecular Weight	614.54
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].[Br-].CC1=C(CCO)SC=[N+]1CCCCCCCCCCCC[N+]2=CSC(CCO)=C2C

InChI

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

HIDE SMILES / InChI

Molecular Formula	C24H40N2O2S2
Molecular Weight	452.717
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800023259 | https://www.ncbi.nlm.nih.gov/pubmed/25470252 | https://www.ncbi.nlm.nih.gov/pubmed/28607017

Albitiazolium (SAR97276) is a clinical antimalarial candidate from a series of choline analogs designed to inhibit plasmodial phospholipid metabolism. Albitiazolium exerts powerful in vitro and in vivo antimalarial activities. Albitiazolium has been shown to have appropriate pharmacokinetic and safety parameters in humans and it was being tested in phase II clinical trials by Sanofi, with confirmed antimalarial activity in adult patients. However, Sanofi discontinued development of Albitiazolium.

Originator

Approval Year

PubMed

Title	Date	PubMed
Transport and pharmacodynamics of albitiazolium, an antimalarial drug candidate.	2012 Aug	22471905
A chemical proteomics approach for the search of pharmacological targets of the antimalarial clinical candidate albitiazolium in Plasmodium falciparum using photocrosslinking and click chemistry.	2014	25470252
High Accumulation and In Vivo Recycling of the New Antimalarial Albitiazolium Lead to Rapid Parasite Death.	2017 Aug	28607017

Sample Use Guides

In Vivo Use Guide

A total of 113 malaria patients received SAR97276. Adults were randomized to receive a single dose SAR97296 given either intramuscularly (IM) (0.18 mg/kg) or intravenously (IV) (0.14 mg/kg). If a single dose was not efficacious a second adult group was planned to test a three dose regimen administered IM once daily for 3 days. Single dose SAR97276 showed insufficient efficacy in adults (IM: 20 of 34 cured, 59%; and IV: 23/30 cured, 77%). The 3-day IM regimen showed acceptable efficacy in adults (27/30, 90%) but not in children (13/19, 68%).

Route of Administration: Parenteral

In Vitro Use Guide

Albitiazolium strongly inhibited in vitro plasmodial growth with an IC50 value of 4.2 nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:15:20 GMT 2023` Edited by `admin` on `Fri Dec 15 16:15:20 GMT 2023`
Record UNII	3AC0AJ4ILP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALBITIAZOLIUM BROMIDE

Official Name

English

albitiazolium bromide [INN]

Common Name

English

3,3'-(DODECAN-1,12-DIYL)BIS(5-(2-HYDROXYETHYL)-4-METHYL-1,3-THIAZOL-3-IUM) DIBROMIDE

Systematic Name

English

SAR97276A

Code

English

SAR-97276A

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C271