210584-54-6

210584-54-6 structure

Name: Amustaline dihydrochloride
Chemical Name: 2-[bis(2-chloroethyl)amino]ethyl 3-(acridin-9-ylamino)propanoate,dihydrochloride
CAS Number: 210584-54-6
Molecular Formula: C₂₂H₂₇Cl₄N₃O₂
Molecular Weight: 507.28100
Catalog: Signaling Pathways Anti-infection Bacterial
Create Date: 2017-09-10 00:43:38
Modify Date: 2024-01-09 11:47:51
Amustaline (S-303) dihydrochloride, a nucleic acid-targeted alkylator, is an efficient pathogen inactivation agent for blood components containing red blood cells. Amustaline dihydrochloride has three components: an acridine anchor (an intercalator that targets nucleic acids non-covalently), an effector (a bis-alkylator group that reacts with nucleophiles), and a linker (a small flexible carbon chain containing a labile ester bond that hydrolyzes at neutral pH to yield non-reactive breakdown products)[1][2].

Name	2-[bis(2-chloroethyl)amino]ethyl 3-(acridin-9-ylamino)propanoate,dihydrochloride
Synonyms	Amustaline Dihydrochloride Amustaline HCl S-303.2HCl UNII-C5MKX7XOYA S 303 dihydrochloride

Description	Amustaline (S-303) dihydrochloride, a nucleic acid-targeted alkylator, is an efficient pathogen inactivation agent for blood components containing red blood cells. Amustaline dihydrochloride has three components: an acridine anchor (an intercalator that targets nucleic acids non-covalently), an effector (a bis-alkylator group that reacts with nucleophiles), and a linker (a small flexible carbon chain containing a labile ester bond that hydrolyzes at neutral pH to yield non-reactive breakdown products)[1][2].
Related Catalog	Signaling Pathways >> Anti-infection >> HIV Research Areas >> Infection Signaling Pathways >> Anti-infection >> Bacterial
In Vitro	S‐303 (200 μM; 20 h) and glutathione (GSH; 20 mM) inactivates high titres of Chikungunya virus (CHIKV) in red blood cells (RBCs)[1]. S-303 (200 μM; 20 h) and GSH (2 mM) inactivates >6.5 logs of HIV, >5.7 logs of Bluetongue virus, >7.0 logs of Yersinia enterocolitica, 4.2 logs of Serratia marcescens, and 7.5 logs of Staphylococcus epidermidis in whole blood experiments[2]. S-303 (200 μM; 20 h) and GSH (20 mM) inactivates approximately 5 logs or greater of Y. enterocolitica, E. coli, S. marcescens, S. aureus, HIV, bovine viral diarrhoea virus, bluetongue virus and human adenovirus 5 in RBC[2]. S-303 (200 μM; 20 h) retains in vitro parameters of RBC function and physiology (including total ATP, extracellular potassium, hemolysis, glucose consumption, lactate production, and pH at 37 °C) compared to conventional RBC[2].
In Vivo	S‐303 RBCs (a single transfusion) is well tolerated in rats (50 μmol/kg) and dogs (70 μmol/kg)[3]. S‐303 RBCs (repeated transfusions) is well tolerated in rats (10 μmol/kg) and dogs (10 μmol/kg) with no histopathologic evidence of organ toxicity[3].
References	[1]. Aubry M, et, al. Amustaline (S-303) treatment inactivates high levels of Chikungunya virus in red-blood-cell components. Vox Sang. 2018 Apr;113(3):232-241. [2]. Mufti NA, et, al. Treatment of whole blood (WB) and red blood cells (RBC) with S-303 inactivates pathogens and retains in vitro quality of stored RBC. Biologicals. 2010 Jan;38(1):14-9. [3]. North A, et, al. Preclinical pharmacokinetic and toxicology assessment of red blood cells prepared with S-303 pathogen inactivation treatment. Transfusion. 2011 Oct;51(10):2208-18.

Boiling Point	575.2ºC at 760 mmHg
Molecular Formula	C₂₂H₂₇Cl₄N₃O₂
Molecular Weight	507.28100
Flash Point	301.7ºC
Exact Mass	505.08600
PSA	57.69000
LogP	5.53870
Vapour Pressure	3.1E-13mmHg at 25°C

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