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Identification
NameAmifostine
Accession NumberDB01143  (APRD00021)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia. [PubChem]
Structure
Thumb
Synonyms
Amifostina
Amifostine
Amifostine Ethiofos
Amifostinum
Aminopropylaminoethyl Thiophosphate
Apaetp
Ethiofos
Ethyol
Gammaphos
SAPEP
WR-1065
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmifostineInjection, powder, lyophilized, for solution500 mg/10mLIntravenousBedford Laboratories2008-04-02Not applicableUs
EthyolInjection, powder, lyophilized, for solution500 mg/10mLIntravenousCumberland Pharmaceuticals Inc.2016-08-01Not applicableUs
Ethyol - Pws IV 500mg/vialPowder, for solution500 mgIntravenousMedimmune Oncology, Inc.1996-12-312008-01-01Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmifostineInjection, powder, lyophilized, for solution50 mg/mLIntravenousSun Pharma Global FZE2008-03-14Not applicableUs
AmifostineInjection, powder, lyophilized, for solution50 mg/mLIntravenousSun Pharmaceutical Industries Limited2008-03-14Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EthyolNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Amifostine trihydrate
112901-68-5
Thumb
  • InChI Key: TXQPXJKRNHJWAX-UHFFFAOYSA-N
  • Monoisotopic Mass: 268.085794576
  • Average Mass: 268.26
DBSALT001833
Categories
UNIIILA426L95O
CAS number20537-88-6
WeightAverage: 214.223
Monoisotopic: 214.054099558
Chemical FormulaC5H15N2O3PS
InChI KeyJKOQGQFVAUAYPM-UHFFFAOYSA-N
InChI
InChI=1S/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)
IUPAC Name
({2-[(3-aminopropyl)amino]ethyl}sulfanyl)phosphonic acid
SMILES
NCCCNCCSP(O)(O)=O
Pharmacology
IndicationFor reduction in the cumulative renal toxicity in patients with ovarian cancer (using cisplatin) and moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer.
Structured Indications
PharmacodynamicsAmifostine is an organic thiophosphate cytoprotective agent indicated to reduce the cumulative renal toxicity associated with repeated administration of cisplatin in patients with advanced ovarian cancer or non-small cell lung cancer and also to reduce the incidence of moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer. Amifostine is a prodrug that is dephosphorylated by alkaline phosphatase in tissues to a pharmacologically active free thiol metabolite, believed to be responsible for the reduction of the cumulative renal toxicity of cisplatin and for the reduction of the toxic effects of radiation on normal oral tissues. Healthy cells are preferentially protected because amifostine and metabolites are present in healthy cells at 100-fold greater concentrations than in tumour cells.
Mechanism of actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1Proteinunknown
inducer
HumanP22413 details
Alkaline phosphatase, placental-likeProteinyes
inducer
HumanP10696 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Amifostine is rapidly dephosphorylated by alkaline phosphatase in tissues primarily to the active free thiol metabolite and, subsequently, to a less active disulfide metabolite.

Route of eliminationAfter a 10-second bolus dose of 150 mg/m2 of ETHYOL, renal excretion of the parent drug and its two metabolites was low during the hour following drug administration, averaging 0.69%, 2.64% and 2.22% of the administered dose for the parent, thiol and disulfide, respectively.
Half life8 minutes
ClearanceNot Available
ToxicityRat LD50: 826 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololAcebutolol may increase the hypotensive activities of Amifostine.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Amifostine is combined with Acetazolamide.Approved, Vet Approved
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Amifostine.Approved
AliskirenAliskiren may increase the hypotensive activities of Amifostine.Approved, Investigational
AlprenololAlprenolol may increase the hypotensive activities of Amifostine.Approved, Withdrawn
AmbrisentanAmbrisentan may increase the hypotensive activities of Amifostine.Approved, Investigational
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Amifostine.Approved
AmiodaroneThe risk or severity of adverse effects can be increased when Amifostine is combined with Amiodarone.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Amifostine.Approved
AmobarbitalAmobarbital may increase the hypotensive activities of Amifostine.Approved, Illicit
Amphotericin BThe risk or severity of adverse effects can be increased when Amifostine is combined with Amphotericin B.Approved, Investigational
Amyl NitriteThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Amifostine.Approved
ApomorphineThe risk or severity of adverse effects can be increased when Amifostine is combined with Apomorphine.Approved, Investigational
ApraclonidineThe risk or severity of adverse effects can be increased when Apraclonidine is combined with Amifostine.Approved
AripiprazoleAripiprazole may increase the hypotensive activities of Amifostine.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Amifostine is combined with Arotinolol.Approved
Arsenic trioxideThe risk or severity of adverse effects can be increased when Amifostine is combined with Arsenic trioxide.Approved, Investigational
AtenololAtenolol may increase the hypotensive activities of Amifostine.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Amifostine.Approved
BarbexacloneBarbexaclone may increase the hypotensive activities of Amifostine.Experimental
BarbitalBarbital may increase the hypotensive activities of Amifostine.Illicit
BarnidipineThe risk or severity of adverse effects can be increased when Amifostine is combined with Barnidipine.Approved
BenazeprilBenazepril may increase the hypotensive activities of Amifostine.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Amifostine.Approved
BepridilBepridil may increase the hypotensive activities of Amifostine.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Amifostine.Approved
BethanidineBethanidine may increase the hypotensive activities of Amifostine.Approved
BimatoprostBimatoprost may increase the hypotensive activities of Amifostine.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Amifostine.Approved
BortezomibThe risk or severity of adverse effects can be increased when Amifostine is combined with Bortezomib.Approved, Investigational
BosentanBosentan may increase the hypotensive activities of Amifostine.Approved, Investigational
BretyliumBretylium may increase the hypotensive activities of Amifostine.Approved
BrimonidineBrimonidine may increase the hypotensive activities of Amifostine.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Amifostine is combined with Bromocriptine.Approved, Investigational
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Amifostine.Approved
BupivacaineThe risk or severity of adverse effects can be increased when Amifostine is combined with Bupivacaine.Approved, Investigational
BupranololBupranolol may increase the hypotensive activities of Amifostine.Approved
CanagliflozinThe risk or severity of adverse effects can be increased when Canagliflozin is combined with Amifostine.Approved
CandesartanCandesartan may increase the hypotensive activities of Amifostine.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Amifostine.Experimental
CaptoprilCaptopril may increase the hypotensive activities of Amifostine.Approved
CarbetocinThe risk or severity of adverse effects can be increased when Amifostine is combined with Carbetocin.Approved
CarteololCarteolol may increase the hypotensive activities of Amifostine.Approved
CarvedilolCarvedilol may increase the hypotensive activities of Amifostine.Approved, Investigational
CeliprololCeliprolol may increase the hypotensive activities of Amifostine.Approved, Investigational
ChlorothiazideChlorothiazide may increase the hypotensive activities of Amifostine.Approved, Vet Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Amifostine is combined with Chlorpromazine.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Amifostine.Approved
CilazaprilCilazapril may increase the hypotensive activities of Amifostine.Approved
CilnidipineThe risk or severity of adverse effects can be increased when Amifostine is combined with Cilnidipine.Approved
ClevidipineThe risk or severity of adverse effects can be increased when Clevidipine is combined with Amifostine.Approved
ClofarabineThe risk or severity of adverse effects can be increased when Amifostine is combined with Clofarabine.Approved, Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Amifostine is combined with Clomipramine.Approved, Vet Approved
ClonidineClonidine may increase the hypotensive activities of Amifostine.Approved
ClozapineThe risk or severity of adverse effects can be increased when Amifostine is combined with Clozapine.Approved
ConivaptanThe risk or severity of adverse effects can be increased when Amifostine is combined with Conivaptan.Approved, Investigational
CryptenamineCryptenamine may increase the hypotensive activities of Amifostine.Approved
CyclothiazideCyclothiazide may increase the hypotensive activities of Amifostine.Approved
DapagliflozinThe risk or severity of adverse effects can be increased when Dapagliflozin is combined with Amifostine.Approved
DebrisoquinDebrisoquin may increase the hypotensive activities of Amifostine.Approved
DeserpidineDeserpidine may increase the hypotensive activities of Amifostine.Approved
DesfluraneThe risk or severity of adverse effects can be increased when Amifostine is combined with Desflurane.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Amifostine.Approved, Vet Approved
DiazoxideDiazoxide may increase the hypotensive activities of Amifostine.Approved
DiclofenamideThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Amifostine.Approved
DihydralazineDihydralazine may increase the hypotensive activities of Amifostine.Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Amifostine.Approved
DinutuximabThe risk or severity of adverse effects can be increased when Dinutuximab is combined with Amifostine.Approved
DipyridamoleThe risk or severity of adverse effects can be increased when Dipyridamole is combined with Amifostine.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Amifostine.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Amifostine.Approved
DuloxetineAmifostine may increase the orthostatic hypotensive activities of Duloxetine.Approved
EfonidipineEfonidipine may increase the hypotensive activities of Amifostine.Approved
EmpagliflozinThe risk or severity of adverse effects can be increased when Empagliflozin is combined with Amifostine.Approved
EnalaprilEnalapril may increase the hypotensive activities of Amifostine.Approved, Vet Approved
EnalaprilatEnalaprilat may increase the hypotensive activities of Amifostine.Approved
EplerenoneThe risk or severity of adverse effects can be increased when Eplerenone is combined with Amifostine.Approved
EpoprostenolEpoprostenol may increase the hypotensive activities of Amifostine.Approved
EprosartanEprosartan may increase the hypotensive activities of Amifostine.Approved
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Amifostine.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Amifostine.Approved
FelodipineFelodipine may increase the hypotensive activities of Amifostine.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Amifostine.Approved
FimasartanThe risk or severity of adverse effects can be increased when Amifostine is combined with Fimasartan.Approved
FosinoprilFosinopril may increase the hypotensive activities of Amifostine.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Amifostine.Approved, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Amifostine.Approved
GuanadrelGuanadrel may increase the hypotensive activities of Amifostine.Approved
GuanethidineGuanethidine may increase the hypotensive activities of Amifostine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Amifostine.Approved, Investigational
HalothaneThe risk or severity of adverse effects can be increased when Amifostine is combined with Halothane.Approved, Vet Approved
HexamethoniumHexamethonium may increase the hypotensive activities of Amifostine.Experimental
HexobarbitalHexobarbital may increase the hypotensive activities of Amifostine.Approved
HydralazineHydralazine may increase the hypotensive activities of Amifostine.Approved
HydrochlorothiazideHydrochlorothiazide may increase the hypotensive activities of Amifostine.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Amifostine.Approved
IloprostThe risk or severity of adverse effects can be increased when Amifostine is combined with Iloprost.Approved, Investigational
ImidaprilImidapril may increase the hypotensive activities of Amifostine.Investigational
ImipramineThe risk or severity of adverse effects can be increased when Amifostine is combined with Imipramine.Approved
IndapamideIndapamide may increase the hypotensive activities of Amifostine.Approved
IndenololIndenolol may increase the hypotensive activities of Amifostine.Withdrawn
IndoraminIndoramin may increase the hypotensive activities of Amifostine.Withdrawn
IrbesartanIrbesartan may increase the hypotensive activities of Amifostine.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Amifostine is combined with Isocarboxazid.Approved
IsofluraneThe risk or severity of adverse effects can be increased when Amifostine is combined with Isoflurane.Approved, Vet Approved
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Isosorbide Dinitrate is combined with Amifostine.Approved
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Isosorbide Mononitrate is combined with Amifostine.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Isoxsuprine is combined with Amifostine.Approved, Withdrawn
IsradipineIsradipine may increase the hypotensive activities of Amifostine.Approved
KetanserinKetanserin may increase the hypotensive activities of Amifostine.Investigational
LabetalolLabetalol may increase the hypotensive activities of Amifostine.Approved
LacidipineLacidipine may increase the hypotensive activities of Amifostine.Approved
LatanoprostLatanoprost may increase the hypotensive activities of Amifostine.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Amifostine.Approved, Investigational
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Amifostine.Approved
LevobupivacaineThe risk or severity of adverse effects can be increased when Amifostine is combined with Levobupivacaine.Approved
LevodopaAmifostine may increase the orthostatic hypotensive activities of Levodopa.Approved
LevosimendanThe risk or severity of adverse effects can be increased when Amifostine is combined with Levosimendan.Approved, Investigational
LisinoprilLisinopril may increase the hypotensive activities of Amifostine.Approved, Investigational
LofexidineLofexidine may increase the hypotensive activities of Amifostine.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Amifostine.Approved
MacitentanMacitentan may increase the hypotensive activities of Amifostine.Approved
ManidipineManidipine may increase the hypotensive activities of Amifostine.Approved
MannitolThe risk or severity of adverse effects can be increased when Mannitol is combined with Amifostine.Approved, Investigational
MecamylamineMecamylamine may increase the hypotensive activities of Amifostine.Approved
MethazolamideThe risk or severity of adverse effects can be increased when Methazolamide is combined with Amifostine.Approved
MethohexitalMethohexital may increase the hypotensive activities of Amifostine.Approved
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Amifostine.Approved
MethyldopaMethyldopa may increase the hypotensive activities of Amifostine.Approved
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Amifostine.Approved
MetipranololMetipranolol may increase the hypotensive activities of Amifostine.Approved
MetolazoneMetolazone may increase the hypotensive activities of Amifostine.Approved
MetoprololMetoprolol may increase the hypotensive activities of Amifostine.Approved, Investigational
MetyrosineMetyrosine may increase the hypotensive activities of Amifostine.Approved
MibefradilMibefradil may increase the hypotensive activities of Amifostine.Withdrawn
MinoxidilMinoxidil may increase the hypotensive activities of Amifostine.Approved
MoexiprilMoexipril may increase the hypotensive activities of Amifostine.Approved
MorphineThe risk or severity of adverse effects can be increased when Amifostine is combined with Morphine.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Amifostine.Approved
NabiloneThe risk or severity of adverse effects can be increased when Amifostine is combined with Nabilone.Approved, Investigational
NadololNadolol may increase the hypotensive activities of Amifostine.Approved
NaftopidilNaftopidil may increase the hypotensive activities of Amifostine.Investigational
NebivololNebivolol may increase the hypotensive activities of Amifostine.Approved, Investigational
NesiritideThe risk or severity of adverse effects can be increased when Nesiritide is combined with Amifostine.Approved, Investigational
NicardipineNicardipine may increase the hypotensive activities of Amifostine.Approved
NicorandilNicorandil may increase the hypotensive activities of Amifostine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Nifedipine is combined with Amifostine.Approved
NiguldipineNiguldipine may increase the hypotensive activities of Amifostine.Experimental
NilvadipineNilvadipine may increase the hypotensive activities of Amifostine.Approved
NimodipineNimodipine may increase the hypotensive activities of Amifostine.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Amifostine.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Amifostine.Approved
Nitric OxideThe risk or severity of adverse effects can be increased when Amifostine is combined with Nitric Oxide.Approved
NitroglycerinThe risk or severity of adverse effects can be increased when Nitroglycerin is combined with Amifostine.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Amifostine.Approved
ObinutuzumabThe risk or severity of adverse effects can be increased when Amifostine is combined with Obinutuzumab.Approved
OlmesartanOlmesartan may increase the hypotensive activities of Amifostine.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Amifostine.Investigational
OxprenololOxprenolol may increase the hypotensive activities of Amifostine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Amifostine is combined with Paclitaxel.Approved, Vet Approved
PapaverineThe risk or severity of adverse effects can be increased when Papaverine is combined with Amifostine.Approved
PargylinePargyline may increase the hypotensive activities of Amifostine.Approved
PenbutololPenbutolol may increase the hypotensive activities of Amifostine.Approved, Investigational
PentobarbitalPentobarbital may increase the hypotensive activities of Amifostine.Approved, Vet Approved
PentoliniumPentolinium may increase the hypotensive activities of Amifostine.Approved
PerindoprilPerindopril may increase the hypotensive activities of Amifostine.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Amifostine is combined with Phenelzine.Approved
PhenobarbitalPhenobarbital may increase the hypotensive activities of Amifostine.Approved
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Amifostine.Approved
PhentolaminePhentolamine may increase the hypotensive activities of Amifostine.Approved
PinacidilPinacidil may increase the hypotensive activities of Amifostine.Withdrawn
PindololPindolol may increase the hypotensive activities of Amifostine.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Amifostine is combined with Pipamperone.Approved
PolythiazidePolythiazide may increase the hypotensive activities of Amifostine.Approved
PramipexoleThe risk or severity of adverse effects can be increased when Amifostine is combined with Pramipexole.Approved, Investigational
PrazosinPrazosin may increase the hypotensive activities of Amifostine.Approved
PrimidonePrimidone may increase the hypotensive activities of Amifostine.Approved, Vet Approved
PropofolThe risk or severity of adverse effects can be increased when Amifostine is combined with Propofol.Approved, Investigational, Vet Approved
PropranololPropranolol may increase the hypotensive activities of Amifostine.Approved, Investigational
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Amifostine.Approved
QuinaprilQuinapril may increase the hypotensive activities of Amifostine.Approved, Investigational
RamiprilRamipril may increase the hypotensive activities of Amifostine.Approved
RasagilineThe risk or severity of adverse effects can be increased when Amifostine is combined with Rasagiline.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Amifostine is combined with Remifentanil.Approved
RemikirenRemikiren may increase the hypotensive activities of Amifostine.Approved
RescinnamineRescinnamine may increase the hypotensive activities of Amifostine.Approved
ReserpineReserpine may increase the hypotensive activities of Amifostine.Approved
RilmenidineRilmenidine may increase the hypotensive activities of Amifostine.Investigational
RiociguatRiociguat may increase the hypotensive activities of Amifostine.Approved
RisperidoneAmifostine may increase the hypotensive activities of Risperidone.Approved, Investigational
RopiniroleThe risk or severity of adverse effects can be increased when Amifostine is combined with Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Amifostine is combined with Ropivacaine.Approved
RotigotineThe risk or severity of adverse effects can be increased when Amifostine is combined with Rotigotine.Approved
SacubitrilThe risk or severity of adverse effects can be increased when Amifostine is combined with Sacubitril.Approved
SaprisartanSaprisartan may increase the hypotensive activities of Amifostine.Experimental
SecobarbitalSecobarbital may increase the hypotensive activities of Amifostine.Approved, Vet Approved
SelegilineThe risk or severity of adverse effects can be increased when Amifostine is combined with Selegiline.Approved, Investigational, Vet Approved
SelexipagSelexipag may increase the hypotensive activities of Amifostine.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Amifostine is combined with Sevoflurane.Approved, Vet Approved
SitaxentanSitaxentan may increase the hypotensive activities of Amifostine.Approved, Investigational, Withdrawn
Sodium NitriteThe risk or severity of adverse effects can be increased when Amifostine is combined with Sodium Nitrite.Approved
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Amifostine.Approved
SpiraprilSpirapril may increase the hypotensive activities of Amifostine.Approved
SpironolactoneThe risk or severity of adverse effects can be increased when Spironolactone is combined with Amifostine.Approved
StreptokinaseThe risk or severity of adverse effects can be increased when Amifostine is combined with Streptokinase.Approved
SufentanilThe risk or severity of adverse effects can be increased when Amifostine is combined with Sufentanil.Approved, Investigational
TamsulosinThe risk or severity of adverse effects can be increased when Amifostine is combined with Tamsulosin.Approved, Investigational
TelmisartanTelmisartan may increase the hypotensive activities of Amifostine.Approved, Investigational
TemocaprilTemocapril may increase the hypotensive activities of Amifostine.Experimental, Investigational
TerazosinThe risk or severity of adverse effects can be increased when Terazosin is combined with Amifostine.Approved
TerlipressinTerlipressin may increase the hypotensive activities of Amifostine.Approved, Investigational
ThalidomideThe risk or severity of adverse effects can be increased when Amifostine is combined with Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThiamylal may increase the hypotensive activities of Amifostine.Approved, Vet Approved
ThiopentalThiopental may increase the hypotensive activities of Amifostine.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Amifostine is combined with Thioridazine.Approved
TiboloneTibolone may increase the hypotensive activities of Amifostine.Approved
TicrynafenTicrynafen may increase the hypotensive activities of Amifostine.Withdrawn
TimololTimolol may increase the hypotensive activities of Amifostine.Approved
TizanidineThe risk or severity of adverse effects can be increased when Tizanidine is combined with Amifostine.Approved
TolazolineTolazoline may increase the hypotensive activities of Amifostine.Approved, Vet Approved
TolcaponeThe risk or severity of adverse effects can be increased when Amifostine is combined with Tolcapone.Approved, Withdrawn
TorasemideTorasemide may increase the hypotensive activities of Amifostine.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Amifostine.Approved
TranylcypromineThe risk or severity of adverse effects can be increased when Amifostine is combined with Tranylcypromine.Approved
TravoprostTravoprost may increase the hypotensive activities of Amifostine.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Amifostine.Approved, Investigational
TretinoinThe risk or severity of adverse effects can be increased when Amifostine is combined with Tretinoin.Approved, Investigational, Nutraceutical
TriamtereneThe risk or severity of adverse effects can be increased when Triamterene is combined with Amifostine.Approved
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Amifostine.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Amifostine.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Amifostine.Approved
UnoprostoneUnoprostone may increase the hypotensive activities of Amifostine.Approved
ValsartanValsartan may increase the hypotensive activities of Amifostine.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Verapamil is combined with Amifostine.Approved
VinpocetineVinpocetine may increase the hypotensive activities of Amifostine.Investigational
XylometazolineXylometazoline may increase the hypotensive activities of Amifostine.Approved
Food InteractionsNot Available
References
Synthesis Reference

Paul E. Kennedy, Roger A. Rajewski, John M. Baldoni, “Crystalline amifostine compositions and methods of the preparation and use of same.” U.S. Patent US5424471, issued April, 1979.

US5424471
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 ]
External Links
ATC CodesV03AF05
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (45.6 KB)
MSDSDownload (36.1 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5944
Blood Brain Barrier-0.8229
Caco-2 permeable-0.6167
P-glycoprotein substrateNon-substrate0.5585
P-glycoprotein inhibitor INon-inhibitor0.9054
P-glycoprotein inhibitor IINon-inhibitor0.9537
Renal organic cation transporterNon-inhibitor0.8451
CYP450 2C9 substrateNon-substrate0.7683
CYP450 2D6 substrateNon-substrate0.7738
CYP450 3A4 substrateNon-substrate0.7689
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8429
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9592
Ames testNon AMES toxic0.5933
CarcinogenicityNon-carcinogens0.717
BiodegradationReady biodegradable0.6316
Rat acute toxicity2.3829 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7047
hERG inhibition (predictor II)Non-inhibitor0.7772
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous50 mg/mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
Powder, for solutionIntravenous500 mg
Prices
Unit descriptionCostUnit
Ethyol 500 mg vial605.88USD vial
Amifostine 500 mg vial600.0USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2120133 No1998-06-092013-07-30Canada
US5424471 No1995-07-312012-07-31Us
US5994409 No1997-12-082017-12-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility1000 mg/mLNot Available
logP-1.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility18.7 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.28 m3·mol-1ChemAxon
Polarizability21.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Zinc ion binding
Specific Function:
By generating PPi, plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. PPi inhibits mineralization by binding to nascent hydroxyapatite (HA) crystals, thereby preventing further growth of these crystals. Preferentially hydrolyzes ATP, but can also hydrolyze other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their c...
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular Weight:
104923.58 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inducer
General Function:
Metal ion binding
Specific Function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular Weight:
57376.515 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Pyrophosphatase activity
Specific Function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular Weight:
57304.435 Da
References
  1. Shaw LM, Bonner H, Lieberman R: Pharmacokinetic profile of amifostine. Semin Oncol. 1996 Aug;23(4 Suppl 8):18-22. [PubMed:8783662 ]
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Drug created on June 13, 2005 07:24 / Updated on December 09, 2016 02:37