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Amifostine

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Name

Amifostine

EINECS
CAS No. 112901-68-5 Density 1.367g/cm3
Solubility Melting Point
Formula C5H21N2O6PS Boiling Point 441.7 °C at 760 mmHg
Molecular Weight 268.27 Flash Point 220.9 °C
Transport Information Appearance
Safety 26-36 Risk Codes 22
Molecular Structure Molecular Structure of 112901-68-5 (Ethanethiol,2-[(3-aminopropyl)amino]-, 1-(dihydrogen phosphate), hydrate (1:3)) Hazard Symbols HarmfulXn
Synonyms

Anifostine trihydrate;Ethanethiol,2-[(3-aminopropyl)amino]-, dihydrogen phosphate (ester), trihydrate (9CI);

 

Amifostine Chemical Properties

Molecular Formula: C5H21N2O6PS
Molar mass: 268.2688 g/mol
Form: Powder
Flash Point: 220.9 °C
Storage temp: 2-8°C
Boiling Point: 441.7 °C at 760 mmHg
Vapour Pressure: 4.9E-09 mmHg at 25°C
Structure of Amifostine (112901-68-5):
              
H-Bond Donor: 7 
H-Bond Acceptor: 8
SMILES: O=P(O)(O)SCCNCCCN.O.O.O 
InChI: InChI=1/C5H15N2O3PS.3H2O/c6-2-1-3-7-4-5-12-11(8,9)10;;;/h7H,1-6H2,(H2,8,9,10);3*1H2 
InChIKey: TXQPXJKRNHJWAX-UHFFFAOYAR 
Std. InChI: InChI=1S/C5H15N2O3PS.3H2O/c6-2-1-3-7-4-5-12-11(8,9)10;;;/h7H,1-6H2,(H2,8,9,10);3*1H2 
Std. InChIKey: TXQPXJKRNHJWAX-UHFFFAOYSA-N

Amifostine Safety Profile

Hazard Codes: Xn
Risk Statements:
22:  Harmful if swallowed 
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing

Amifostine Specification

 Amifostine (112901-68-5), which also can be called for 2-(3-Aminopropylamino)ethylsulfanylphosphonic acid trihydrate ; Ethanethiol, 2-((3-aminopropyl)amino)-, dihydrogen phosphate (ester), trihydrate ; Anifostine trihydrate , is a cytoprotective adjuvant and also commonly known as WR-1065 in its active form. It is marketed by MedImmune under the trade name Ethyol. It is used therapeutically to reduce the incidence of neutropenia-related fever and infection induced by DNA-binding chemotherapeutic agents including platinum-containing agents (e.g. cisplatin ) and alkylating agents (e.g. cyclophosphamide ). Amifostine (112901-68-5) is also indicated to reduce the incidence of xerostomia in patients undergoing radiotherapy for head and neck cancer and to reduce the cumulative renal toxicity from cisplatin in non-small cell lung cancer; And also used to decrease the cumulative nephrotoxicity associated with platinum-containing agents. However, while nephroprotection was observed, the fact that amifostine could protect tumors could not be excluded. Given better treatment options for non-small cell lung cancer, this indication was withdrawn in 2005.
Amifostine (112901-68-5) is an organic thiophosphate prodrug which is hydrolysed in vivo by alkaline phosphatase to the active cytoprotective thiol metabolite, and, can only be administered intravenously, after reconstitution with normal saline. The selective protection of non-malignant tissues is believed to be due to higher alkaline phosphatase activity, higher pH, and vascular permeation of normal tissues.
Common side effects of it include hypocalcemia, diarrhea, vomiting, nausea, sneezing, hiccoughs, and somnolence. Serious side effects include:  erythema multiforme,hypotension (found in 62% of patients), Stevens-Johnson syndrome and toxic epidermal necrolysis, immune hypersensitivity syndrome, anaphylaxis, erythroderma, and loss of consciousness (rare).

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