AMUSTALINE DIHYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H25Cl2N3O2.2ClH
Molecular Weight	507.281
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.ClCCN(CCCl)CCOC(=O)CCNC1=C2C=CC=CC2=NC3=C1C=CC=C3

InChI

InChIKey=WEOLKSYHLNAIRH-UHFFFAOYSA-N

InChI=1S/C22H25Cl2N3O2.2ClH/c23-10-13-27(14-11-24)15-16-29-21(28)9-12-25-22-17-5-1-3-7-19(17)26-20-8-4-2-6-18(20)22;;/h1-8H,9-16H2,(H,25,26);2*1H

HIDE SMILES / InChI

Molecular Formula	C22H25Cl2N3O2
Molecular Weight	434.359
Charge	0
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C75926 | https://www.interceptbloodsystem.com/en/blood-center/intercept/mechanism-action-amustaline | https://www.ncbi.nlm.nih.gov/pubmed/29314033

Amustaline (S-303) is a quinacrine mustard compound with potential antineoplastic activity. Amustaline binds to, intercalates and crosslinks DNA and RNA. This agent is mainly used for ex vivo purposes, specifically for the inactivation of pathogens such as viruses, protozoa and bacteria in red blood cells (RBCs). When S-303 is added to red blood cells, the compound rapidly passes through membranes, including those of cells and viral envelopes, due to its amphipathic character, and intercalates into helical regions of the nucleic acids of pathogens and white blood cells. TERCEPTTMBlood System usingamustaline (S-303) and glutathione (GSH) was able to inactivate high levels of DENV and ZIKV in RBCs. S-303 system has been shown to effectively inactivate a broad spectrum of pathogens, while maintaining RBC quality.

Originator

Approval Year

PubMed

Title	Date	PubMed
Pathogen inactivation of Dengue virus in red blood cells using amustaline and glutathione.	2017 Dec	28921542
Red blood cells treated with the amustaline (S-303) pathogen reduction system: a transfusion study in cardiac surgery.	2018 Apr	29498049
Amustaline (S-303) treatment inactivates high levels of Chikungunya virus in red-blood-cell components.	2018 Apr	29314033

Patents

Sample Use Guides

In Vitro Use Guide

0.2mM S-303 and 2mM glutathione (GSH) inactivated >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. A series of studies in RBC showed that 0.2mM S-303 and 20mM GSH inactivated 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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:03:15 GMT 2023` Edited by `admin` on `Fri Dec 15 16:03:15 GMT 2023`
Record UNII	C5MKX7XOYA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMUSTALINE DIHYDROCHLORIDE

Official Name

English

S-303 DIHYDROCHLORIDE

Code

English

2-[Bis(2-chloroethyl)amino]ethyl 3-(acridin-9-ylamino)propanoate dihydrochloride

Systematic Name

English

AMUSTALINE DIHYDROCHLORIDE [USAN]

Common Name

English

.BETA.-ALANINE, N-9-ACRIDINYL-, 2-(BIS(2-CHLOROETHYL)AMINO)ETHYL ESTER, DIHYDROCHLORIDE

Systematic Name

English

S-303.2HCL

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1590