U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H25Cl2N3O2
Molecular Weight 434.359
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMUSTALINE

SMILES

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

InChI

InChIKey=BDLWRIAFNYVGTC-UHFFFAOYSA-N
InChI=1S/C22H25Cl2N3O2/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)

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pathogen inactivation of Dengue virus in red blood cells using amustaline and glutathione.
2017 Dec
Patents

Sample Use Guides

In Vitro Use Guide
Curator's Comment: A series of experiments were performed in whole blood (WB) to measure the level of viral and bacterial inactivation.
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 16:03:26 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:26 GMT 2023
Record UNII
25571657UW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMUSTALINE
Common Name English
.BETA.-ALANINE, N-9-ACRIDINYL-, 2-(BIS(2-CHLOROETHYL)AMINO)ETHYL ESTER
Common Name English
S-303
Code English
2-(BIS(2-CHLOROETHYL)AMINO)ETHYL 3-(ACRIDIN-9-YLAMINO)PROPANOATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1590
Created by admin on Fri Dec 15 16:03:26 GMT 2023 , Edited by admin on Fri Dec 15 16:03:26 GMT 2023
Code System Code Type Description
FDA UNII
25571657UW
Created by admin on Fri Dec 15 16:03:26 GMT 2023 , Edited by admin on Fri Dec 15 16:03:26 GMT 2023
PRIMARY
CAS
220180-88-1
Created by admin on Fri Dec 15 16:03:26 GMT 2023 , Edited by admin on Fri Dec 15 16:03:26 GMT 2023
PRIMARY
NCI_THESAURUS
C75926
Created by admin on Fri Dec 15 16:03:26 GMT 2023 , Edited by admin on Fri Dec 15 16:03:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID20176473
Created by admin on Fri Dec 15 16:03:26 GMT 2023 , Edited by admin on Fri Dec 15 16:03:26 GMT 2023
PRIMARY
PUBCHEM
6433104
Created by admin on Fri Dec 15 16:03:26 GMT 2023 , Edited by admin on Fri Dec 15 16:03:26 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY