Amifostine

Product Name: Amifostine
CAS No.: 20537-88-6
Chemical Name: Amifostine
Synonyms: Ethyol;γphos;sapep;Ethyo;WR2721;CS-271;apaetp;wr2721c;Ethiotas;ym-08310
CBNumber: CB1316377
Molecular Formula: C5H15N2O3PS
Formula Weight: 214.22
MOL File: 20537-88-6.mol

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Amifostine Property

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.
pka: 1.28±0.10(Predicted)
form: powder
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.
InChI: 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: S(P(O)(O)=O)CCNCCCN
CAS DataBase Reference: 20537-88-6(CAS DataBase Reference)

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Safety

Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38
Safety Statements: 26-36
WGK Germany: 3
RTECS: TE6491000
Hazardous Substances Data: 20537-88-6(Hazardous Substances Data)
Toxicity: cyt-mus-ipr 300 mg/kg CUSCAM 54,1080,85

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Tocris

Product number: 6655
Product name: Amifostine
Packaging: 100
Price: $102
Updated: 2021/12/16

TRC

Product number: A576810
Product name: Amifostine
Packaging: 100mg
Price: $55
Updated: 2021/12/16

ChemScene

Product number: CS-2875
Product name: Amifostine
Purity: ≥98.0%
Packaging: 10mg
Price: $65
Updated: 2021/12/16

AK Scientific

Product number: H037
Product name: Amifostine
Packaging: 5mg
Price: $34
Updated: 2021/12/16

ChemScene

Product number: CS-2875
Product name: Amifostine
Purity: ≥98.0%
Packaging: 50mg
Price: $272
Updated: 2021/12/16

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Amifostine Chemical Properties,Usage,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

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

Uses

neuroleptic

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] Chemoprotective and radioprotective effects of amifostine: an update of clinical trials
[2] MAURO PROVINCIALI . In vivo amifostine (WR-2721) prevents chemotherapy-induced apoptosis of peripheral blood lymphocytes from cancer patients[J]. Life sciences, 1999, 64 17: Pages 1525-1532. DOI:10.1016/s0024-3205(99)00096-x
[3] MICHAEL I KOUKOURAKIS. Amifostine before chemotherapy: improved tolerance profile of the subcutaneous over the intravenous route.[J]. Clinical Cancer Research, 2003, 9 9: 3288-3293.
[4] DANIELA MAURICI. Amifostine (WR2721) restores transcriptional activity of specific p53 mutant proteins in a yeast functional assay[J]. Oncogene, 2001, 20 27: 3533-3540. DOI:10.1038/sj.onc.1204428

Amifostine Preparation Products And Raw materials

Raw materials

Sodium thiophosphate N-hydroxyethyl propylene diamine N-(2-bromoethyl)propane-1,3-diamine 1,2-Diaminopropane

Preparation Products

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View Lastest Price from Amifostine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Amifostine 20537-88-6
Price: US $0.00/g
Min. Order: 1g
Purity: 98.0%
Supply Ability: 5kg/month
Release date: 2021-12-13

Hebei Zhanyao Biotechnology Co. Ltd

Product: Amifostine 20537-88-6
Price: US $10.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 99%
Supply Ability: 20 Tons
Release date: 2021-10-29

Dideu Industries Group Limited

Product: Amifostine 20537-88-6
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons min
Release date: 2021-08-13

20537-88-6, AmifostineRelated Search:

N-(n-Butyl)thiophosphoric triamide 6-Aminocaproic acid Ethylparaben 2-(2-Aminoethylamino)ethanol Methyl acrylate N,N-Diisopropylethylamine Azamethiphos Ethanol ISOXADIFEN-ETHYL Ethyl acetate Glycine Tris(trimethylsilyl)phosphate Phosphorodithioic acid, mixed O,O-bis(1,3-dimethylbutyl and iso-Pr) esters, zinc salts Zinc Dialkyl Dithio Phosphate(ZDDP) Anifostine trihydrate AMIFOSTINE HYDRATE Ethanethiol AMifostine Disulfide

Ethyol

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

CS-271

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

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|||WR2721|||Gammaphos

Amifostine, cytoprotective agent

20537-88-6

C5H15N2O3PS

Cancer Research

Antitumor Agents

BioChemical

Therapy Adjuncts

Active Pharmaceutical Ingredients

Radioprotective Agent

Intermediates & Fine Chemicals

Pharmaceuticals

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Sulfur & Selenium Compounds