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Amifostine

CAS No.
20537-88-6
Chemical Name:
Amifostine
Synonyms
Ethyol;γphos;sapep;Ethyo;WR2721;apaetp;CS-271;wr2721c;Ethiotas;ym-08310
CBNumber:
CB1316377
Molecular Formula:
C5H15N2O3PS
Molecular Weight:
214.22
MDL Number:
MFCD00233058
MOL File:
20537-88-6.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

Amifostine Properties

Melting point 160-1610C
Boiling point 441.7±51.0 °C(Predicted)
Density 1.367±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in Water.
form powder
pka 1.28±0.10(Predicted)
color White
Water Solubility Soluble to 100 mM in water
Stability Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
CAS DataBase Reference 20537-88-6(CAS DataBase Reference)
NCI Dictionary of Cancer Terms amifostine; Ethyol
FDA UNII ILA426L95O
NCI Drug Dictionary amifostine
ATC code V03AF05

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
Hazard Codes  Xn,Xi
Risk Statements  22-36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  TE6491000
Toxicity cyt-mus-ipr 300 mg/kg CUSCAM 54,1080,85

Amifostine price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Tocris 6655 Amifostine 20537-88-6 100 $102 2021-12-16 Buy
TRC A576810 Amifostine 20537-88-6 100mg $55 2021-12-16 Buy
ChemScene CS-2875 Amifostine ≥98.0% 20537-88-6 10mg $65 2021-12-16 Buy
AK Scientific H037 Amifostine 20537-88-6 5mg $34 2021-12-16 Buy
ChemScene CS-2875 Amifostine ≥98.0% 20537-88-6 50mg $272 2021-12-16 Buy
Product number Packaging Price Buy
6655 100 $102 Buy
A576810 100mg $55 Buy
CS-2875 10mg $65 Buy
H037 5mg $34 Buy
CS-2875 50mg $272 Buy

Amifostine Chemical Properties,Uses,Production

Description

Amifostine, an organic thiophosphate, was introduced for the reduction of cisplatin-induced renal toxicity in patients with advanced ovarian cancer. It is also a radio-protective agent. Amifostine is a prodrug which is rapidly dephosphorylated, preferentially in non-tumor tissues to the active thiol. This agent binds to chemotherapeutic drugs and free radicals released by radiotherapy. The protective effect of amifostine was observed in a wide range of normal organs including bone marrow and gastrointestinal mucosa without interfering with the anti-tumor effect of chemohadiotherapy, indicating an increased therapeutic index for existing cancer treatment. Amifostine is also being evaluated as a cytoprotective in other types of tumors including lung, breast, head and neck cancers. It was reported to be a potent mucolytic with potential in cystic fibrosis.

Chemical Properties

White Solid

Originator

US Bloscience (U.S.A.)

Uses

neuroleptic

Uses

It is a thiophosphate derivative of cysteamine; provides normal cells with selective protection against the toxic effects of cancer chemotherapy and radiation treatment

Definition

ChEBI: An organic thiophosphate that is the S-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy.

Manufacturing Process

A solution of 2-(3-aminopropylamino)ethanol (25.0 g, 0.212 mole) in 48 % hydrobromic acid (200 ml) was distilled until 35 ml of distillate had been collected. The solution was refluxed and, periodically, more distillate was collected. The total volume of distillate removed in 7 distillation periods was 160 ml, or 80 % of the original volume of 48% hydrobromic acid, and the time of continuous boiling was approximately 48 hours. The residual solution was then evaporated to dryness under reduced pressure with the aid of several added portions of methanol. The crystalline residue was thoroughly triturated with acetone, collected, and washed on the funnel with acetone. After the product had been pressed as dry as possible on the funnel, it was dissolved in a slight excess of boiling methanol and the solution was filtered. Addition of acetone to the filtrate precipitated pure N-(2-bromoethyl)-1,3- propanediamine dihydrobromide as colorless crystals, which were dried in vacuum over phosphorus pentoxide: yield 58.0 g (80%), melting point 205- 206°C. Trisodium phosphorothioate (6.93 g, 38.5 mmoles) was gradually added in small portions with vigorous stirring to water (38 ml) cooled externally by means of a water bath (15°-20°C). To the resulting suspension was added N-(2-bromoethyl)-1,3-propanediamine dihydrobromide (13.3 g, 38.8 mmoles). After a few minutes, complete solution occurred, and N,Ndimethylformamide (19 ml) was added with continued external cooling at 15°- 20°C. After the solution had been stirred at about 20°C for 90 min, it was poured into methanol (250 ml), and the mixture was refrigerated at 4°C overnight. The white precipitate that formed was collected and pressed as dry as possible on the funnel. The solid was dissolved in water (40 ml), and the solution was filtered. Addition of methanol (250 ml) reprecipitated the product. After the mixture had been refrigerated about 1 hour, the product was collected and washed on the funnel, first with methanol and finally with ether. The white solid was dried in vacuo at room temperature, then exposed to ambient conditions of the laboratory for 5 hours, and bottled under nitrogen and stored in a freezer. The yield of S-2-(3-aminopropylamino)ethyl dihydrogen phosphorothioate monohydrate, melting point (from methanol) 160-161°C, dec., was 8.15 g (91%).

brand name

Ethyol (MedImmune) [USAN previously used: Ethiofos.].

Therapeutic Function

Radioprotective, Chemoprotectant, Mucolytic

Safety Profile

Poison by intravenous,intramuscular, and intraperitoneal routes. Moderately toxicby ingestion. An experimental teratogen. Otherexperimental reproductive effects. Mutation data reported. When heated todecomposition it emits very toxic fumes of SOx, PO

storage

Store at +4°C

References

1) Capizzi et al. (2000), Chemoprotective and radioprotective effects of amifostine: an update of clinical trials; Int. J. Hematol., 72 425 2) Provinciali et al. (1999), In vivo amifostine (WR-2721) prevents chemotherapy-induced apoptosis of peripheral blood lymphocytes from cancer patients; Life Sci., 64 1525 3) Koukourakis et al. (2004), Amifostine before chemotherapy: improved tolerance profile of the subcutaneous over the intravenous route; Cancer Chemother. Pharmacol., 53 8 4) Maurici et al. (2001), Amifostine (WR2721) restores transcriptional activity of specific p53 mutant proteins in a yeast functional assay; Oncogene, 20 3533

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View Lastest Price from Amifostine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Amifostine pictures 2021-12-14 Amifostine
20537-88-6
US $0.00 / g 1g 98.0% 5kg/month WUHAN FORTUNA CHEMICAL CO., LTD
Amifostine pictures 2021-10-30 Amifostine
20537-88-6
US $10.00 / Kg/Bag 1Kg/Bag 99% 20 Tons Hebei Zhanyao Biotechnology Co. Ltd
Amifostine USP/EP/BP pictures 2021-08-14 Amifostine USP/EP/BP
20537-88-6
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
  • Amifostine pictures
  • Amifostine
    20537-88-6
  • US $0.00 / g
  • 98.0%
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Amifostine pictures
  • Amifostine
    20537-88-6
  • US $10.00 / Kg/Bag
  • 99%
  • Hebei Zhanyao Biotechnology Co. Ltd

Amifostine Spectrum

γphos Fosteamine 2-(3-Aminopropyl)aminoethyl phosphorothioate, WR2721 Ethiotas S-2-[(3-Aminopropyl)amino]ethanethiol dihydrogen phosphate ester Amifostine,2-(3-Aminopropyl)aminoethyl phosphorothioate, WR2721 AMifostine anhydrous AMifostine(Ethiofos) AMIFOSTIN AMINOPROPYL AMINOETHYLTHIOPHOSPHATE AaMifostine 2-(3-aminopropylamino)ethylsulfanylphosphonic acid WR2721 2-((3-aminopropyl)amino)-ethanethiodihydrogenphosphate(ester) 2-[3-AMINOPROPYL]AMINOETHYL PHOSPHOROTHIOATE S-2-(3-AMINOPROPYLAMINO)ETHYL O,O-DIHYDROGEN PHOSPHOROTHIOATE sapep s-omega-(3-aminopropylamino)ethyldihydrogenphosphorothioate wr2721c ym-08310 2-[(3-Aminopropyl)-amino]ethanethiol Dihydrogen Phosphate CSC-296961 Ethyo 2-(3-aminopropyl)-aminoethyl-phosphorothioate (Amifostin) Ethanethiol, 2-[(3-aminopropyl)amino]-, 1-(dihydrogen phosphate) Amifostine Ethiofos Phosphorothioic acid S-(2-((3-aminopropyl)amino)ethyl) ester 2-((3-aminopropyl)amino)-ethanethiol,dihydrogenphosphateester 2-(3-aminopropylamino)ethylthiophosphate acide((amino-3propylamino)-2ethyl)-s-phosphorothioique apaetp au-95722 gammaphos nsc-296961 s-(2-(3-aminopropylamino)ethyl)phosphorothioate s,2-(3-aminopropylamino)ethyl-phosphorothioicacid CS-271 Amifostine USP/EP/BP Amifostine impurity AmifostineQ: What is Amifostine Q: What is the CAS Number of Amifostine Q: What is the storage condition of Amifostine Q: What are the applications of Amifostine TIANFUCHEM--20537-88-6--High purity Amifostine factory price Ethyol 20537-88-6 C5H15N2O3PS Cancer Research Antitumor Agents BioChemical Therapy Adjuncts Active Pharmaceutical Ingredients Radioprotective Agent Intermediates & Fine Chemicals Pharmaceuticals TIAPRIDAL Sulfur & Selenium Compounds