CHEBI:2636 - amifostine

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ChEBI Name amifostine
ChEBI ID CHEBI:2636
Definition An organic thiophosphate that is the S-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C5H15N2O3PS
Net Charge 0
Average Mass 214.22404
Monoisotopic Mass 214.054
InChI InChI=1S/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)
InChIKey JKOQGQFVAUAYPM-UHFFFAOYSA-N
SMILES NCCCNCCSP(O)(O)=O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
radiation protective agent

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ChEBI Ontology
Outgoing amifostine (CHEBI:2636) has functional parent cysteamine (CHEBI:17141)
amifostine (CHEBI:2636) has role antioxidant (CHEBI:22586)
amifostine (CHEBI:2636) has role prodrug (CHEBI:50266)
amifostine (CHEBI:2636) has role radiation protective agent (CHEBI:66987)
amifostine (CHEBI:2636) is a diamine (CHEBI:23666)
amifostine (CHEBI:2636) is a organic thiophosphate (CHEBI:37512)
IUPAC Name
S-{2-[(3-aminopropyl)amino]ethyl} dihydrogen thiophosphate
INNs Sources
amifostina ChEBI
amifostine ChemIDplus
amifostinum ChEBI
Synonym Source
Amifostine KEGG COMPOUND
Brand Name Source
Ethyol DrugBank
Manual Xrefs Databases
156 DrugCentral
Amifostine Wikipedia
C06819 KEGG COMPOUND
DB01143 DrugBank
HMDB0015274 HMDB
LSM-4721 LINCS
US3892824 Patent
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Registry Numbers Types Sources
20537-88-6 CAS Registry Number ChemIDplus
2088122 Reaxys Registry Number Reaxys
2088122 Beilstein Registry Number Beilstein
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Last Modified
22 February 2017