Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H19NO4.ClH |
| Molecular Weight | 337.798 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1=C(COCCN)C2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
InChI
InChIKey=MHLAMQBABOJZQW-UHFFFAOYSA-N
InChI=1S/C17H19NO4.ClH/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;1H
| 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 |
| Molecular Formula | C17H19NO4 |
| Molecular Weight | 301.3371 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| 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 |
|
| Improving the bacteriological safety of platelet transfusions. | 2004 Jan |
|
| Functional characteristics of photochemically treated platelets. | 2004 Mar |
|
| 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 |
|
| Amotosalen photochemical inactivation of severe acute respiratory syndrome coronavirus in human platelet concentrates. | 2005 Aug |
|
| Fresh frozen plasma prepared with amotosalen HCl (S-59) photochemical pathogen inactivation: transfusion of patients with congenital coagulation factor deficiencies. | 2005 Aug |
|
| In vitro photochemical inactivation of cell-associated human T-cell leukemia virus Type I and II in human platelet concentrates and plasma by use of amotosalen. | 2005 Jul |
|
| Amotosalen-treated donor T cells have polyclonal antigen-specific long-term function without graft-versus-host disease after allogeneic bone marrow transplantation. | 2005 Mar |
|
| Amotosalen interactions with platelet and plasma components: absence of neoantigen formation after photochemical treatment. | 2005 Oct |
|
| Polymerase chain reaction inhibition assay documenting the amotosalen-based photochemical pathogen inactivation process of platelet concentrates. | 2005 Sep |
|
| Leishmania inactivation in human pheresis platelets by a psoralen (amotosalen HCl) and long-wavelength ultraviolet irradiation. | 2005 Sep |
|
| Therapeutic efficacy and safety of photochemically treated apheresis platelets processed with an optimized integrated set. | 2005 Sep |
|
| Pathogen inactivation techniques. | 2006 |
|
| The role of photochemical treatment with amotosalen and UV-A light in the prevention of transfusion-transmitted cytomegalovirus infections. | 2006 Jan |
|
| Photochemical treatment of plasma with amotosalen and long-wavelength ultraviolet light inactivates pathogens while retaining coagulation function. | 2006 Jul |
|
| Risks of fresh frozen plasma and platelets. | 2006 Jun |
|
| A randomized, controlled Phase III trial of therapeutic plasma exchange with fresh-frozen plasma (FFP) prepared with amotosalen and ultraviolet A light compared to untreated FFP in thrombotic thrombocytopenic purpura. | 2006 Oct |
|
| Photochemical treatment of plasma with amotosalen and UVA light: process validation in three European blood centers. | 2008 Apr |
|
| Effects of intercept pathogen inactivation on platelet function as analysed by free oscillation rheometry. | 2008 Feb |
|
| 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 |
|
| Assessment of safety in neonates for transfusion of platelets and plasma prepared with amotosalen photochemical pathogen inactivation treatment by a 1-month intravenous toxicity study in neonatal rats. | 2009 May |
|
| 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 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:28:07 GMT 2023
by
admin
on
Fri Dec 15 15:28:07 GMT 2023
|
| Record UNII |
67B255SI5F
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C582
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NCI_THESAURUS |
C25760
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NCI_THESAURUS |
C2163
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C72699
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159598
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300000044601
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67B255SI5F
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CHEMBL2110621
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161262-45-9
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DTXSID70167093
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MM-24
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C118577
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