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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:18 UTC
HMDB IDHMDB0015274
Secondary Accession Numbers
  • HMDB15274
Metabolite Identification
Common NameAmifostine
DescriptionAmifostine is only found in individuals that have used or taken this drug. It is a phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia. [PubChem]The thiol metabolite is responsible for most of the cytoprotective and radioprotective properties of amifostine. It is readily taken up by cells where it binds to and detoxifies reactive metabolites of platinum and alkylating agents as well as scavenges free radicals. Other possible effects include inhibition of apoptosis, alteration of gene expression and modification of enzyme activity.
Structure
Data?1582753278
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 Weight214.223
Monoisotopic Molecular Weight214.054099558
IUPAC Name({2-[(3-aminopropyl)amino]ethyl}sulfanyl)phosphonic acid
Traditional Nameamifostine
CAS Registry Number20537-88-6
SMILES
NCCCNCCSP(O)(O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.7 g/LNot Available
LogP-1.9Not Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available146.74931661259
DarkChem[M-H]-PredictedNot Available141.20331661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9300000000-8f3e83d23b65b9a187692017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-5350b8c906608c1eb7e42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-bcddc871edb434e577ae2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-2900000000-58ff84f991edcac36e7d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05nb-9200000000-ef847b9b156a08e7fa172017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-9000000000-c58215f6bca055f13ab72017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014s-2930000000-d9f7a8f51a3e0639844f2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kal-9500000000-deee317641b354488f7c2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9200000000-b4b822595957219239b72016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-7690000000-f26c0991b61c8d4975ac2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003s-7900000000-4a37816d6ed768e56c532016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dm-9800000000-940b1a6dd1f6e79e9c0f2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01143 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01143 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01143
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2056
KEGG Compound IDC06819
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmifostine
METLIN IDNot Available
PubChem Compound2141
PDB IDNot Available
ChEBI ID2636
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Santini V, Giles FJ: The potential of amifostine: from cytoprotectant to therapeutic agent. Haematologica. 1999 Nov;84(11):1035-42. [PubMed:10553165 ]
  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. [PubMed:22187663 ]
  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. [PubMed:21175348 ]
  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. [PubMed:19895691 ]
  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. [PubMed:23237540 ]
  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. [PubMed:21945096 ]
  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. [PubMed:19334055 ]
  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. [PubMed:22962271 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
References
  1. Shaw LM, Bonner H, Lieberman R: Pharmacokinetic profile of amifostine. Semin Oncol. 1996 Aug;23(4 Suppl 8):18-22. [PubMed:8783662 ]
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
References
  1. Capizzi RL: The preclinical basis for broad-spectrum selective cytoprotection of normal tissues from cytotoxic therapies by amifostine. Semin Oncol. 1999 Apr;26(2 Suppl 7):3-21. [PubMed:10348255 ]
  2. Orditura M, De Vita F, Roscigno A, Infusino S, Auriemma A, Iodice P, Ciaramella F, Abbate G, Catalano G: Amifostine: A selective cytoprotective agent of normal tissues from chemo-radiotherapy induced toxicity (Review). Oncol Rep. 1999 Nov-Dec;6(6):1357-62. [PubMed:10523712 ]
  3. Santini V, Giles FJ: The potential of amifostine: from cytoprotectant to therapeutic agent. Haematologica. 1999 Nov;84(11):1035-42. [PubMed:10553165 ]
  4. Plasswilm L, Hanjalic A, Hoeper J, Cordes N, Tannapfel A: Microvessel density and endothelial cell proliferation after amifostine (Ethyol) administration in vivo. Anticancer Res. 1999 Sep-Oct;19(5B):4241-5. [PubMed:10628381 ]
  5. Buschini A, Anceschi E, Carlo-Stella C, Regazzi E, Rizzoli V, Poli P, Rossi C: Amifostine (WR-2721) selective protection against melphalan genotoxicity. Leukemia. 2000 Sep;14(9):1642-51. [PubMed:10995012 ]
General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]