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W2020

Sigma-Aldrich

WR-1065

≥98% (HPLC)

Synonym(s):

2-[(3-Aminopropyl)amino]ethanethiol dihydrochloride, WR-1065 dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C5H14N2S · 2HCl
CAS Number:
14653-77-1
Molecular Weight:
207.16
MDL number:
MFCD00460339
UNSPSC Code:
12352200
PubChem Substance ID:
329830444
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

H2O: ≥20 mg/mL

storage temp.

−20°C

SMILES string

Cl.Cl.NCCCNCCS

InChI

1S/C5H14N2S.2ClH/c6-2-1-3-7-4-5-8;;/h7-8H,1-6H2;2*1H

InChI key

XDRLRDHLCIFZIW-UHFFFAOYSA-N

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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.
WR-1065 is the active metabolite of the prodrug amifostine, generated by alkaline phosphatase. It is found to accumulate in many epithelial tissues. WR-1065 protects cellular membranes and DNA from free radical induced damage.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dale M Walker et al.
Environmental and molecular mutagenesis, 50(6), 460-472 (2009-04-01)
The success of nucleoside reverse transcriptase inhibitors (NRTIs) in treating HIV-1 infection and reducing mother-to-child transmission of the virus during pregnancy is accompanied by evidence that NRTIs cause long-term health risks for cancer and mitochondrial disease. Thus, agents that mitigate
David J Grdina et al.
International journal of radiation oncology, biology, physics, 73(3), 886-896 (2009-02-14)
To determine whether amifostine can induce elevated manganese superoxide dismutase (SOD2) in murine tissues and a transplantable SA-NH tumor, resulting in a delayed tumor cell radioprotective effect. SA-NH tumor-bearing C3H mice were treated with a single 400 mg/kg or three
Modulation of the clastogenic activity of ionizing radiation and bleomycin by the aminothiol WR-1065.
L G Littlefield et al.
Environmental and molecular mutagenesis, 22(4), 225-230 (1993-01-01)
David R Cassatt et al.
International journal of radiation oncology, biology, physics, 61(3), 901-907 (2005-02-15)
The cytoprotective drug amifostine (Ethyol) protects rats from oral mucositis resulting from a single dose of gamma-irradiation. We expanded earlier studies to determine whether multiple doses of amifostine protect against fractionated or hyperfractionated radiation and whether the active metabolite of
Zaki S Badawy et al.
Fertility and sterility, 91(1), 173-178 (2008-01-22)
To determine the effect of 4-hydroperoxycyclophosphamide (4OOH-CP) on the respiration of human sperm, and investigate the protective properties of mesna and WR-1065. SUNY Upstate Medical University, Syracuse, NY. Men (n = 12) visited the Andrology Department for fertility evaluation. None.
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