Amifostine (CHEM016559)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:37:01 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016559
Identification
Common NameAmifostine
ClassSmall Molecule
DescriptionA phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AmifostinaChEBI
AmifostinumChEBI
EthyolChEBI
Amifostine ethiofosHMDB
Aminopropylaminoethyl thiophosphateHMDB
ApaetpHMDB
EthiofosHMDB
GammaphosHMDB
SAPEPHMDB
WR-1065HMDB
Alza brand OF amifostineHMDB
Amifostine disodium saltHMDB
Amifostine trihydrateHMDB
Anhydrous, amifostineHMDB
Anhydrous, ethiofosHMDB
Monohydrochloride, amifostineHMDB
S-(N-(3-Aminopropyl)-2-aminoethyl)thiophosphoric acidHMDB
Schering plough brand OF amifostineHMDB
Amifostine alza brandHMDB
Amifostine monohydrochlorideHMDB
Disodium salt, amifostineHMDB
Trihydrate, amifostineHMDB
US bioscience brand OF amifostineHMDB
Amifostine lilly brandHMDB
Aminopropylaminoethylthiophosphoric acidHMDB
Essex brand OF amifostineHMDB
Ethiofos anhydrousHMDB
Lilly brand OF amifostineHMDB
Schering-plough brand OF amifostineHMDB
Amifostine anhydrousHMDB
Amifostine essex brandHMDB
Amifostine monohydrateHMDB
Amifostine schering-plough brandHMDB
Aminopropyl aminoethylthiophosphateHMDB
AminopropylaminoethylthiophosphateHMDB
Monohydrate, amifostineHMDB
Acid, aminopropylaminoethylthiophosphoricHMDB
Ethanethiol, 2-((3-aminopropyl)amino)-, dihydrogen phosphate (ester), trihydrateHMDB
Chemical FormulaC5H15N2O3PS
Average Molecular Mass214.223 g/mol
Monoisotopic Mass214.054 g/mol
CAS Registry Number20537-88-6
IUPAC Name({2-[(3-aminopropyl)amino]ethyl}sulfanyl)phosphonic acid
Traditional Nameamifostine
SMILESNCCCNCCSP(O)(O)=O
InChI IdentifierInChI=1S/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)
InChI KeyJKOQGQFVAUAYPM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganothiophosphorus compounds
Sub ClassNot Available
Direct ParentOrganothiophosphorus compounds
Alternative Parents
Substituents
  • Sulfenyl compound
  • Secondary amine
  • Organothiophosphorus compound
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.7 g/LALOGPS
logP-1.4ALOGPS
logP-3.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.06ChemAxon
pKa (Strongest Basic)11.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area95.58 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.28 m³·mol⁻¹ChemAxon
Polarizability21.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9300000000-8f3e83d23b65b9a18769Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-5350b8c906608c1eb7e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-bcddc871edb434e577aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-2900000000-58ff84f991edcac36e7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05nb-9200000000-ef847b9b156a08e7fa17Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-9000000000-c58215f6bca055f13ab7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014s-2930000000-d9f7a8f51a3e0639844fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kal-9500000000-deee317641b354488f7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9200000000-b4b822595957219239b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-7690000000-f26c0991b61c8d4975acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003s-7900000000-4a37816d6ed768e56c53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dm-9800000000-940b1a6dd1f6e79e9c0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0390000000-2033745753817e8b82afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-220c1777754513503a2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9000000000-8b437daef02c3cdba4c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-c0bd8a7c35f5f698e7fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-19aa33fa42f40d1742f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01143
HMDB IDHMDB0015274
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmifostine
Chemspider ID2056
ChEBI ID2636
PubChem Compound ID2141
Kegg Compound IDC06819
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Santini V, Giles FJ: The potential of amifostine: from cytoprotectant to therapeutic agent. Haematologica. 1999 Nov;84(11):1035-42.
2. Xu Y, Parmar K, Du F, Price BD, Sun Y: The radioprotective agent WR1065 protects cells from radiation damage by regulating the activity of the Tip60 acetyltransferase. Int J Biochem Mol Biol. 2011;2(4):295-302. Epub 2011 Oct 20.
3. Murley JS, Kataoka Y, Miller RC, Li JJ, Woloschak G, Grdina DJ: SOD2-mediated effects induced by WR1065 and low-dose ionizing radiation on micronucleus formation in RKO human colon carcinoma cells. Radiat Res. 2011 Jan;175(1):57-65. doi: 10.1667/RR2349.1. Epub 2010 Nov 8.
4. Poirier MC, Olivero OA, Hardy AW, Franchini G, Borojerdi JP, Walker VE, Walker DM, Shearer GM: Antiretroviral activity of the aminothiol WR1065 against Human Immunodeficiency virus (HIV-1) in vitro and Simian Immunodeficiency virus (SIV) ex vivo. AIDS Res Ther. 2009 Nov 6;6:24. doi: 10.1186/1742-6405-6-24.
5. Grdina DJ, Murley JS, Miller RC, Mauceri HJ, Sutton HG, Thirman MJ, Li JJ, Woloschak GE, Weichselbaum RR: A manganese superoxide dismutase (SOD2)-mediated adaptive response. Radiat Res. 2013 Feb;179(2):115-24. doi: 10.1667/RR3126.2. Epub 2012 Dec 13.
6. Murley JS, Baker KL, Miller RC, Darga TE, Weichselbaum RR, Grdina DJ: SOD2-mediated adaptive responses induced by low-dose ionizing radiation via TNF signaling and amifostine. Free Radic Biol Med. 2011 Nov 15;51(10):1918-25. doi: 10.1016/j.freeradbiomed.2011.08.032. Epub 2011 Sep 3.
7. Walker DM, Kajon AE, Torres SM, Carter MM, McCash CL, Swenberg JA, Upton PB, Hardy AW, Olivero OA, Shearer GM, Poirier MC, Walker VE: WR1065 mitigates AZT-ddI-induced mutagenesis and inhibits viral replication. Environ Mol Mutagen. 2009 Jul;50(6):460-72. doi: 10.1002/em.20482.
8. Mereniuk TR, Maranchuk RA, Schindler A, Penner-Chea J, Freschauf GK, Hegazy S, Lai R, Foley E, Weinfeld M: Genetic screening for synthetic lethal partners of polynucleotide kinase/phosphatase: potential for targeting SHP-1-depleted cancers. Cancer Res. 2012 Nov 15;72(22):5934-44. doi: 10.1158/0008-5472.CAN-12-0939. Epub 2012 Sep 7.
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=10553165
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=10942928
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=11013273
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=11201306
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=11984063
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=12005544
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=12433814
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=12499421
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=12561384
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=12751907
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=14980067
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=15380592
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=15698860
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=15875769
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=16465691
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=17602063
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=18072151
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=18549666
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=19712749
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=20334641
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=21347716
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=21646919
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=22267539
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=22402174
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=22440042
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=22456378
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=22496587
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=22643562
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=22844290
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=22878481
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=22885239
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=22989457
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=23040218
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=23052919
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=23092832
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=23401928
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=8612469
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=8683243