amifostine (CHEBI:2636)

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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

Average Mass

214.22404

Monoisotopic Mass

214.05410

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 Any compound that is able to protect normal cells from the damage caused by radiation therapy.

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

Synonym	Source
Amifostine	KEGG COMPOUND

Brand Name	Source
Ethyol	DrugBank

Last Modified

22 February 2017