Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H19NO4 |
| Molecular Weight | 301.3371 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(COCCN)C2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
InChI
InChIKey=FERWCFYKULABCE-UHFFFAOYSA-N
InChI=1S/C17H19NO4/c1-9-6-15(19)22-16-10(2)17-13(7-12(9)16)14(11(3)21-17)8-20-5-4-18/h6-7H,4-5,8,18H2,1-3H3
Amotosalen (S-59, psoralen derivative), a chemical capable of binding to nucleic acids is added to platelets. UVA illumination (320 – 400 nm wavelengths) of amotosalen-treated platelet components induces covalent cross-linking of any nucleic acids to which amotosalen is bound; thereby, preventing further replication. Amotosalen is used in the INTERCEPT process to cross-link DNA and RNA. Amotosalen has protective activity against pathogens such as bacteria, viruses, protozoa, and leukocytes. Prior to administration amotosalen is added to plasma and platelets, then in vivo this agent penetrates pathogens and targets DNA and RNA. Upon activation by ultraviolet A light, amotosalen forms interstrand DNA and RNA crosslinks and prevents replication. Thus, the pathogen-inactivation system using amotosalen/ultraviolet A offers the potential to mitigate the risk of ZIKV transmission by plasma and platelet transfusion. Inactivation of leukocytes can prevent graft versus host disease upon transfusion.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Preclinical safety of a nucleic acid-targeted Helinx compound: a clinical perspective. | 2001 Oct |
|
| Pharmacokinetic study of FFP photochemically treated with amotosalen (S-59) and UV light compared to FFP in healthy volunteers anticoagulated with warfarin. | 2002 Oct |
|
| Amotosalen: Allogeneic Cellular Immunotherapies system, INTERCEPT Plasma System, INTERCEPT Platelet System, S 59. | 2003 |
|
| Allogeneic T cells treated with amotosalen prevent lethal cytomegalovirus disease without producing graft-versus-host disease following bone marrow transplantation. | 2003 Dec 1 |
|
| Transfusion of pooled buffy coat platelet components prepared with photochemical pathogen inactivation treatment: the euroSPRITE trial. | 2003 Mar 15 |
|
| In vitro evaluation of COM.TEC apheresis platelet concentrates using a preparation set and pathogen inactivation over a storage period of five days. | 2004 |
|
| In vitro evaluation of pooled buffy coat platelets treated with photochemical pathogen inactivation using amotosalen. | 2004 Apr |
|
| Recovery and life span of 111indium-radiolabeled platelets treated with pathogen inactivation with amotosalen HCl (S-59) and ultraviolet A light. | 2004 Dec |
|
| Implementation of the INTERCEPT Blood System for Platelets into routine blood bank manufacturing procedures: evaluation of apheresis platelets. | 2004 May |
|
| Inactivation of viruses in platelet concentrates by photochemical treatment with amotosalen and long-wavelength ultraviolet light. | 2005 Apr |
|
| Fresh frozen plasma prepared with amotosalen HCl (S-59) photochemical pathogen inactivation: transfusion of patients with congenital coagulation factor deficiencies. | 2005 Aug |
|
| Amotosalen-treated donor T cells have polyclonal antigen-specific long-term function without graft-versus-host disease after allogeneic bone marrow transplantation. | 2005 Mar |
|
| Polymerase chain reaction inhibition assay documenting the amotosalen-based photochemical pathogen inactivation process of platelet concentrates. | 2005 Sep |
|
| Pathogen inactivation of platelets with a photochemical treatment with amotosalen HCl and ultraviolet light: process used in the SPRINT trial. | 2006 Apr |
|
| Quantification of viral inactivation by photochemical treatment with amotosalen and UV A light, using a novel polymerase chain reaction inhibition method with preamplification. | 2006 Dec 15 |
|
| Platelet dose consistency and its effect on the number of platelet transfusions for support of thrombocytopenia: an analysis of the SPRINT trial of platelets photochemically treated with amotosalen HCl and ultraviolet A light. | 2006 Jan |
|
| Risks of fresh frozen plasma and platelets. | 2006 Jun |
|
| Transfusion of 7-day-old amotosalen photochemically treated buffy-coat platelets to patients with thrombocytopenia: a pilot study. | 2006 Mar |
|
| Platelets photochemically treated with amotosalen HCl and ultraviolet A light correct prolonged bleeding times in patients with thrombocytopenia. | 2006 May |
|
| Transfusion-transmitted infections. | 2007 Jun 6 |
|
| Photochemical inactivation with amotosalen and long-wavelength ultraviolet light of Plasmodium and Babesia in platelet and plasma components. | 2008 Aug |
|
| Coagulation function in fresh-frozen plasma prepared with two photochemical treatment methods: methylene blue and amotosalen. | 2008 Jan |
|
| An active haemovigilance programme characterizing the safety profile of 7437 platelet transfusions prepared with amotosalen photochemical treatment. | 2008 May |
|
| Quantitative analysis of DNA interstrand cross-links and monoadducts formed in human cells induced by psoralens and UVA irradiation. | 2008 Nov 15 |
|
| INTERCEPT plasma: comparability with conventional fresh-frozen plasma based on coagulation function--an in vitro analysis. | 2010 Jan |
|
| Transfusion-transmitted parasitic infections. | 2010 Jul |
|
| An active hemovigilance program characterizing the safety profile of 7483 transfusions with plasma components prepared with amotosalen and UVA photochemical treatment. | 2010 Jun |
|
| Monitoring photochemical pathogen inactivation treatment using amotosalen and ultraviolet-A light: evaluation of an indicator label. | 2010 Nov |
|
| The how's and why's of evidence based plasma therapy. | 2010 Sep |
Patents
Sample Use Guides
Using the LDA assay, treatment with 150 uM of
amotosalen and 1.0–3.0 J/cm2 UVA light inactivated
>5.4 – 0.3 log of T cells in single donor plateletpheresis
units. The minimum concentration of amotosalen required to inactivate T cells after illumination with 1 J/cm2 of UVA light was 0.05 uM.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C582
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
159599
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY | |||
|
K1LDZ0VBC0
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY | |||
|
C76756
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY | |||
|
CHEMBL2110621
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY | |||
|
8118
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY | |||
|
C118577
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY | |||
|
161262-29-9
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY | |||
|
300000036914
Created by
admin on Fri Dec 15 16:03:25 GMT 2023 , Edited by admin on Fri Dec 15 16:03:25 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
