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
| 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 |
|---|---|---|
| Amotosalen: Allogeneic Cellular Immunotherapies system, INTERCEPT Plasma System, INTERCEPT Platelet System, S 59. | 2003 |
|
| 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 |
|
| 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 |
|
| Facilitating T-cell immune reconstitution after haploidentical transplantation in adults. | 2004 Nov-Dec |
|
| Photochemical treatment of platelet concentrates with amotosalen and long-wavelength ultraviolet light inactivates a broad spectrum of pathogenic bacteria. | 2004 Oct |
|
| 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 |
|
| Clinical safety of platelets photochemically treated with amotosalen HCl and ultraviolet A light for pathogen inactivation: the SPRINT trial. | 2005 Dec |
|
| Effect of the psoralen-based photochemical pathogen inactivation on mitochondrial DNA in platelets. | 2005 Dec |
|
| 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 |
|
| 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 |
|
| In vitro evaluation of Haemonetics MCS+ apheresis platelet concentrates treated with photochemical pathogen inactivation following plasma volume reduction using the INTERCEPT Preparation Set. | 2006 Feb |
|
| 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 |
|
| The role of photochemical treatment with amotosalen and UV-A light in the prevention of transfusion-transmitted cytomegalovirus infections. | 2006 Jan |
|
| Transfusion of 7-day-old amotosalen photochemically treated buffy-coat platelets to patients with thrombocytopenia: a pilot study. | 2006 Mar |
|
| Cytokine accumulation in photochemically treated and gamma-irradiated platelet concentrates during storage. | 2006 May |
|
| Platelets photochemically treated with amotosalen HCl and ultraviolet A light correct prolonged bleeding times in patients with thrombocytopenia. | 2006 May |
|
| Leukoreduced buffy coat-derived platelet concentrates photochemically treated with amotosalen HCl and ultraviolet A light stored up to 7 days: assessment of hemostatic function under flow conditions. | 2007 Apr |
|
| The efficacy of photochemical treatment with amotosalen HCl and ultraviolet A (INTERCEPT) for inactivation of Trypanosoma cruzi in pooled buffy-coat platelets. | 2007 Mar |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:03:25 GMT 2023
by
admin
on
Fri Dec 15 16:03:25 GMT 2023
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| Record UNII |
K1LDZ0VBC0
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C582
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159599
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K1LDZ0VBC0
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C76756
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CHEMBL2110621
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8118
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C118577
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161262-29-9
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300000036914
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