| Identification | Back Directory | [Name]
Amifostine Thiol Dihydrochloride | [CAS]
14653-77-1 | [Synonyms]
WR-1065 2HCl
AMifostine Thiol
WR-1065 dihydrochloride
Amifostine Thiol Dihydrochloride
Amifostine Thiol Dihydrochloride (90%)
Amifostine Impurity 2（Amifostine Thiol）
2-[(3-AMinopropyl)aMino]ethanethiol Hydrochloride
2-[(3-Aminopropyl)amino]ethanethioldihydrochloride
2-[(3-aminopropyl)amino]ethane-1-thiol dihydrochloride
Amifostine Thiol (50 mg) (2-[(3-aminopropyl)amino]ethanethiol, dihydrochloride) | [Molecular Formula]
C5H14N2S | [MDL Number]
MFCD00460339 | [MOL File]
14653-77-1.mol | [Molecular Weight]
134.243 |
| Chemical Properties | Back Directory | [Melting point ]
184-186°C | [storage temp. ]
-20°C | [solubility ]
H2O: ≥20mg/mL | [form ]
powder | [color ]
white to off-white | [Water Solubility ]
H2O: ≥20mg/mL | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C5H14N2S/c6-2-1-3-7-4-5-8/h7-8H,1-6H2 | [InChIKey]
YHPLKWQJMAYFCN-UHFFFAOYSA-N | [SMILES]
NCCCNCCS |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-41 | [Safety Statements ]
26-39-41 | [WGK Germany ]
3 | [HS Code ]
2930909165 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1 | [Toxicity]
mouse,LD50,intraperitoneal,400mg/kg (400mg/kg),European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 24, Pg. 48, 1989. |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
A metabolite of Amifostine. | [Biological Activity]
wr-1065, a dephosphorylated metabolite of amifostine?(ethyol), can protect against the immediate and delayed effects of radiation exposure.wr-1065 can protect against zidovudine (azt) – induced genetoxicity. the lymphoblastoid cell line molt-3 cells were exposed to 0/10μm azt for 96h. in the first 24h 0/5?μm wr-1065 was added and cyt b was added in 76h in the cells, the viability of azt treated molt-3 cells did not altered.[1] moreover, in rko36 cell lines (derivative rko human colorectal carcinoma carrying a gfp-pcmv-egfp2xho), 4 mm final concentration (ec50) wr-1065 treatment for 30min immediately before irradiation showed protective effects against cell chromosomal damage and death induced by ionizing radiation and delayed genomic instability. but 40??m wr-1065 did not show immediate radio-protective effects in irradiated rko36 cells.[2] wr-1065 acts as radioprotective agents mainly through suppression of the homologous recombination pathway. in spd8 chinese hamster cell line, both 4 mm wr-1065 for 30min and 10 ?m for 24h significantly reduced the homologous recombination induced by 0.2 mm hydroxyurea for 24h or 100 nm camptothecin for 1h. while wr-1065 did not show its radioprotective effects in irradiated homologous recombination-deficient irs 1sf cells compared with homologous recombination-proficient cells aa8/cxr3(p＜0.05).[3]with spray drying technique using plga (polylactide co-glycolide) as the polymer matrix, wr-1065 were prepared into nanoparticles. 500mg/kg wr-1065/plga nanoparticles in which containing 21.7(w/w wr-1065) were administrated orally in mice to determined its radio-protective role. wr-1065plga nanoparticles treatment mice showed noteworthy higher 30-day survival, less bone marrow suppression and less intestinal injury compared non-treated control mice, indicated its significant radio-protective effects.[4] | [Biochem/physiol Actions]
WR-1065 is cytoprotective cell-permeable reactive oxygen species scavenger and p53 activator and re-activator. Recently shown to have antiretroviral activity and an active metabolite of Amifostine which selectively protects normal tissues from the damaging effects of anti-neoplastic radiation therapy. | [in vivo]
The results show that Amifostine thiol dihydrochloride (Amifostine thiol) attenuates the severity of 6-OHDA-induced catalepsy (P<0.001) when compare with 6-OHDA-lesioned rats. Also it has been observed that Amifostine thiol dihydrochloride improves catalepsy in dose dependent manner (P<0.001). Pretreatment with three different doses of Amifostine thiol dihydrochloride (20, 40 and 80 μg/2 μL/rat) for 3 days before 6-OHDA administration, significantly (P<0.001) elevates SOD activity and restores it to normal range compare with 6-OHDA lesioned rats[3]. | [storage]
Desiccate at -20°C | [References]
[1]. ofelia a . olivero, michael o. ong, han nan m. braun, ariadna marrogi, kathyiani divi, james b. mitchel l, and miriam c. poirier. selective protection of zidovadine-induced dna-damage by antioxidants wr-1065 and tempol. environmental and molecular mutagenesis (2014)55: 566-572
[2]. jaroslaw dziegielewski, janet e. baulch, wilfried goetz, mitchell c. coleman, douglas r. spitz, jeffrey s. murley, david j. grdina, and william f. morgan. wr-1065, the active metabolite of amifostine, mitigates radiation-induced delayed genomic instability. free radic biol med. (2008)45(12): 1674–1681
[3]. jaroslaw dziegielewski, wilfried goetz, jeffrey s. murley, david j. grdina, william f. morgan, and janet e. baulch. amifostine metabolite wr-1065 disrupts homologous recombination in mammalian cells. radiat res. (2010) 173(2): 175–183
[4]. sarala pamujula,?vimal kishore,?barbara rider,?krishna c. agrawal, and?tarun k. mandal. radioprotection in mice following oral administration of wr-1065/plga nanoparticles. (2008) 84(11): 900-908 |
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