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Substance Name: Amifostine [USAN:INN:BAN]
RN: 20537-88-6
UNII: ILA426L95O
InChIKey: JKOQGQFVAUAYPM-UHFFFAOYSA-N

Note

  • A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.

Molecular Formula

  • C5-H15-N2-O3-P-S

Molecular Weight

  • 214.2245
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Protectant (Topical)
  • Protective Agents
  • Radiation-Protective Agents
  • Radioprotector
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Amifostine
  • Amifostine [USAN:INN:BAN]

MeSH Heading

  • Amifostine

Synonyms

  • 2-(3-Aminopropylamino)ethyl thiophosphate
  • Acide ((amino-3 propylamino)-2 ethyl)-S-phosphorothioique
  • Acide ((amino-3 propylamino)-2 ethyl)-S-phosphorothioique [French]
  • Amifostine
  • Aminopropylaminoethyl thiophosphate
  • Apaetp
  • AU-95722
  • BRN 2088122
  • CCRIS 9316
  • Ethiofos
  • Ethiofos anhydrous
  • Ethyol
  • Gammaphos
  • HSDB 7560
  • NSC 296961
  • NSC-296961
  • S 8744
  • S,2-(3-Aminopropylamino)ethyl-phosphorothioic acid
  • S-(2-((3-Aminopropyl)amino)ethyl) dihydrogen phosphorothioate
  • S-(2-(3-Aminopropylamino)ethyl) phosphorothioate
  • S-2-(3-Aminopropylamino)ethyl phosphorothioic acid
  • S-omega-(3-Aminopropylamino)ethyl dihydrogen phosphorothioate
  • Sapep
  • UNII-ILA426L95O
  • WR 2721
  • YM 08310
  • YM-08310

Systematic Names

  • 2-((3-Aminopropyl)amino)-ethanethiol, dihydrogen phosphate ester (9CI)
  • Ethanethiol, 2-((3-aminopropyl)amino)-, dihydrogen phosphate (ester)
  • Phosphorothioic acid, S-(2-(3-aminopropylamino)ethyl) ester

Registry Numbers

CAS Registry Number

  • 20537-88-6

FDA UNII

  • ILA426L95O

Other Registry Number

  • 53028-04-9

Related Registry Numbers

  • 59178-37-9 (di-hydrochloride salt)
  • 63717-27-1 (monohydrate)

System Generated Number

  • 0020537886

Structure Descriptors

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 279mg/kg (279mg/kg)   Toxicologic Pathology. Vol. 13, Pg. 58, 1985.
dog LDLo intravenous 279mg/kg (279mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicologic Pathology. Vol. 13, Pg. 58, 1985.
guinea pig LD50 intraperitoneal 407mg/kg (407mg/kg)   Radiobiologiya. Vol. 16, Pg. 249, 1976.
guinea pig LD50 oral 635mg/kg (635mg/kg)   National Technical Information Service. Vol. AD758-432,
man TDLo oral 11mg/kg (11mg/kg)   National Technical Information Service. Vol. AD758-432,
man TDLo oral 11mg/kg (11mg/kg) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"

GASTROINTESTINAL: NAUSEA OR VOMITING
National Technical Information Service. Vol. AD758-432,
monkey LD50 oral > 10gm/kg (10000mg/kg)   National Technical Information Service. Vol. AD758-432,
mouse LD50 intramuscular 514mg/kg (514mg/kg)   Radiobiologiya. Vol. 16, Pg. 249, 1976.
mouse LD50 intraperitoneal 321mg/kg (321mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 557mg/kg (557mg/kg)   National Technical Information Service. Vol. PB81-199580,
mouse LD50 intravenous 557mg/kg (557mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
National Technical Information Service. Vol. PB81-199580,
mouse LD50 oral 842mg/kg (842mg/kg)   Radiobiologiya. Vol. 20, Pg. 746, 1980.
rat LD50 intramuscular 396mg/kg (396mg/kg)   Radiobiologiya. Vol. 16, Pg. 249, 1976.
rat LD50 intraperitoneal 418mg/kg (418mg/kg)   Radiobiologiya. Vol. 16, Pg. 249, 1976.
rat LD50 oral 826mg/kg (826mg/kg)   National Technical Information Service. Vol. AD758-432,

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.070 (none)   EST
Atmospheric OH Rate Constant 1.41E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.