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CAS No.: | 20537-88-6 |
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Name: | Amifostine |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C5H15N2O3PS |
Molecular Weight: | 214.225 |
Synonyms: | WR 2721;2-(3-aminopropylamino)ethylsulfanylphosphonic acid;Gammaphos;Aminopropylaminoethyl thiophosphate;Ethanethiol,2-[(3-aminopropyl)amino]-,dihydrogen phosphate (ester);Ethiofos;S-(2-(3-Aminopropylamino)ethyl) phosphorothioate;S-[2-[(3-Aminopropyl)amino]ethyl] dihydrogen phosphorothioate;AU-95722;Phosphorothioic acid, S-[2-[ (3-aminopropyl)amino]ethyl]ester;YM 08310;WR 2721C;Ethanethiol, S-[ (3-aminopropyl)amino]-, dihydrogen phosphate- (ester);SAPEP;2-(3-Aminopropylamino)ethyl thiophosphate;S-[2-(3-Aminopropylamino)ethyl] phosphorothioate;Ethanethiol, 2-[ (3-aminopropyl)amino]-, dihydrogen phosphate (ester);Aminopropyl aminoethylthiophosphate;S-2-(3-aminopropylamino)ethyl O,O-dihydrogen phosphorothioate; |
EINECS: | 633-786-4 |
Density: | 1.367 g/cm3 |
Melting Point: | 160.161 °C |
Boiling Point: | 441.7 °C at 760 mmHg |
Flash Point: | 220.9 °C |
Solubility: | Soluble in water |
Appearance: | White solid |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 22-36/37/38 |
Safety: | 26-36 |
PSA: | 130.69000 |
LogP: | 0.84190 |
The IUPAC name of Aminopropyl aminoethylthio-phosphate is 2-(3-aminopropylamino)ethylsulfanylphosphonic acid. With the CAS registry number 20537-88-6, it is also named as Amifostine. The product's categories are Active Pharmaceutical Ingredients; Radioprotective Agent; Intermediates & Fine Chemicals; Pharmaceuticals. It is white solid which is highly toxic and flammable. When heated to decomposition it emits very toxic fumes of SOx, POx, and NOx. So the storage environment should be well-ventilated, low-temperature and dry.
The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.68; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -4.64; (4)ACD/LogD (pH 7.4): -4.32; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 77.12 Å2; (13)Index of Refraction: 1.554; (14)Molar Refractivity: 50.28 cm3; (15)Molar Volume: 156.6 cm3; (16)Surface Tension: 64.6 dyne/cm; (17)Enthalpy of Vaporization: 76.64 kJ/mol; (18)Vapour Pressure: 4.9E-09 mmHg at 25°C; (19)Rotatable Bond Count: 7; (20)Exact Mass: 214.0541; (21)MonoIsotopic Mass: 214.0541; (22)Topological Polar Surface Area: 121; (23)Heavy Atom Count: 12; (24)Complexity: 152.
Preparation of Aminopropyl aminoethylthio-phosphate: It can be obtained by the following reaction:
Uses of Aminopropyl aminoethylthio-phosphate: It is a cytoprotective adjuvant used in cancer chemotherapy and radiotherapy involving DNA-binding chemotherapeutic agents. It is also used to decrease the cumulative nephrotoxicity associated with platinum-containing agents. In addition, it canreact with 2-chloro-1-indol-3-yl-ethanone to get S-[9-(indol-3-yl)-3,7-diaza-9-oxononyl]thiophosphoric acid. This reaction needs reagent Et3N and solvents H2O, dimethylformamide at temperature of 85-90 °C. The reaction time is 1 hours. The yield is 51%.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:O=P(O)(O)SCCNCCCN
2. InChI:InChI=1/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)
3. InChIKey:JKOQGQFVAUAYPM-UHFFFAOYAT
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 279mg/kg (279mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | 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) | GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)" | 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) | 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, |