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Details

Stereochemistry ACHIRAL
Molecular Formula C5H15N2O3PS
Molecular Weight 214.223
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMIFOSTINE ANHYDROUS

SMILES

NCCCNCCSP(O)(O)=O

InChI

InChIKey=JKOQGQFVAUAYPM-UHFFFAOYSA-N
InChI=1S/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)

HIDE SMILES / InChI

Molecular Formula C5H15N2O3PS
Molecular Weight 214.223
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/?term=17602063

Amifostine is an organic thiophosphate cytoprotective agent known chemically as 2-[(3¬ aminopropyl)amino]ethanethiol dihydrogen phosphate (ester), it’s adjuvant used in cancer chemotherapy and radiotherapy involving DNA-binding chemotherapeutic agents. It is marketed under the trade name Ethyol. Amifostine is a prodrug and is dephosphorylated by alkaline phosphatase in tissues to a pharmacologically active free thiol metabolite. This metabolite is 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. The ability of Ethyol to differentially protect normal tissues is attributed to the higher capillary alkaline phosphatase activity, higher pH and better vascularity of normal tissues relative to tumor tissue, which results in a more rapid generation of the active thiol metabolite as well as a higher rate constant for uptake into cells. The higher concentration of the thiol metabolite in normal tissues is available to bind to, and thereby detoxify, reactive metabolites of cisplatin. This thiol metabolite can also scavenge reactive oxygen species generated by exposure to either cisplatin or radiation. Healthy cells are preferentially protected because amifostine and metabolites are present in healthy cells at 100-fold greater concentrations than in tumor cells.

CNS Activity

Curator's Comment: Because amifostine does not cross the blood–brain barrier, the central nervous system, often the dose-limiting organ in radiotherapy, is not protected

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
ETHYOL

Approved Use

Amifostine for Injection is indicated to reduce the cumulative renal toxicity associated with repeated administration of cisplatin in patients with advanced ovarian cancer. Amifostine for Injection is indicated to reduce the incidence of moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer, where the radiation port includes a substantial portion of the parotid glands (see Clinical Studies ). For the approved indications, the clinical data do not suggest that the effectiveness of cisplatin based chemotherapy regimens or radiation therapy is altered by Amifostine for Injection. There are at present only limited data on the effects of amifostine on the efficacy of chemotherapy or radiotherapy in other settings. Amifostine should not be administered to patients in other settings where chemotherapy can produce a significant survival benefit or cure, or in patients receiving definitive radiotherapy, except in the context of a clinical study (see WARNINGS).

Launch Date

1995
Secondary
ETHYOL

Approved Use

Amifostine for Injection is indicated to reduce the cumulative renal toxicity associated with repeated administration of cisplatin in patient s with advanced ovarian cancer. Amifostine for Injection is indicated to reduce the incidence of moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer, where the radiation port includes a substantial portion of the parotid glands (see Clinical Studies ). For the approved indications, the clinical data do not suggest that the effectiveness of cisplatin based chemotherapy regimens or radiation therapy is altered by Amifostine for Injection. There are at present only limited data on the effects of amifostine on the efficacy of chemotherapy or radiotherapy in other settings. Amifostine should not be administered to patients in other settings where chemotherapy can produce a significant survival benefit or cure, or in patients receiving definitive radiotherapy, except in the context of a clinical study (see WARNINGS).

Launch Date

1995
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8 min
910 mg/m² 1 times / day other, intravenous
dose: 910 mg/m²
route of administration: Intravenous
experiment type: OTHER
co-administered:
AMIFOSTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 200 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Nausea and vomiting, Nausea and vomiting...
Other AEs:
Nausea and vomiting (grade 3-4, 8%)
Nausea and vomiting (all grades, 53%)
Hypotension (grade 3-4, 3%)
Hypotension (all grades, 15%)
Sources:
910 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 910 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 910 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Blood pressure decreased...
Other AEs: Nausea and vomiting, Nausea and vomiting...
AEs leading to
discontinuation/dose reduction:
Blood pressure decreased (<3%)
Other AEs:
Nausea and vomiting (grade 3-4, 30%)
Nausea and vomiting (all grades, 96%)
Hypotension (grade 3-4, 8%)
Hypotension (all grades, 61%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypotension all grades, 15%
200 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 200 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea and vomiting all grades, 53%
200 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 200 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Hypotension grade 3-4, 3%
200 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 200 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea and vomiting grade 3-4, 8%
200 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 200 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Blood pressure decreased <3%
Disc. AE
910 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 910 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 910 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Hypotension all grades, 61%
910 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 910 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 910 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea and vomiting all grades, 96%
910 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 910 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 910 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea and vomiting grade 3-4, 30%
910 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 910 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 910 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Hypotension grade 3-4, 8%
910 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 910 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 910 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

For Reduction of Cumulative Renal Toxicity with Chemotherapy: The recommended starting dose is 910 mg/m2 administered once daily as a 15-minute infusion. For Reduction of Moderate to Severe Xerostomia from Radiation of the Head and Neck: The recommended dose is 200 mg/m2 administered once daily as a 3-minute infusion starting 15-30 minutes prior to standard fraction radiation therapy (1.8-2.0 Gy). infusion, starting 30 minutes prior to chemotherapy.
Route of Administration: Intravenous
Human pulmonary EC were grown on golden microelectrodes. Cells were pretreated with WR-1065 (unprotected form of amifostine, used for cell culture treatments) (0.4 mM, 1 mM or 4 mM, 30 min) followed by stimulation with 250 mM H2O2 (Panel A). EC were pretreated with 4 mM
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:07:31 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:31 GMT 2025
Record UNII
ILA426L95O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-758236
Preferred Name English
AMIFOSTINE ANHYDROUS
Common Name English
S-(2-((3-AMINOPROPYL)AMINO)ETHYL) DIHYDROGEN PHOSPHOROTHIOATE
Systematic Name English
Amifostine [WHO-DD]
Common Name English
AMIFOSTINE [JAN]
Common Name English
WR-2721
Code English
PHOSPHOROTHIOIC ACID S-(2-((3-AMINOPROPYL)AMINO)ETHYL) ESTER
Systematic Name English
AMIFOSTINE [MI]
Common Name English
ETHANETHIOL, 2-((3-AMINOPROPYL)AMINO)-, DIHYDROGEN PHOSPHATE (ESTER)
Common Name English
AMIFOSTINE [HSDB]
Common Name English
amifostine [INN]
Common Name English
2-((3-AMINOPROPYL)AMINO)ETHANETHIOL 1-(DIHYDROGEN PHOSPHATE)
Common Name English
YM-08310
Code English
AMINOPROPYLAMINOETHYL THIOPHOSPHATE
Systematic Name English
ETHIOFOS ANHYDROUS
Common Name English
Classification Tree Code System Code
NDF-RT N0000180854
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
NDF-RT N0000000170
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
NCI_THESAURUS C2080
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
Code System Code Type Description
DRUG BANK
DB01143
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
CAS
20537-88-6
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
FDA UNII
ILA426L95O
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
NSC
758236
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
PUBCHEM
2141
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
MERCK INDEX
m1669
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY Merck Index
HSDB
7560
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
NCI_THESAURUS
C66724
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
RXCUI
1545987
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY RxNorm
SMS_ID
100000077704
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
EVMPD
SUB12846MIG
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID8022585
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
DAILYMED
ILA426L95O
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
INN
4941
Created by admin on Mon Mar 31 18:07:31 GMT 2025 , Edited by admin on Mon Mar 31 18:07:31 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE ACTIVE -> PARENT
MINOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC