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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 a cytoprotective cell-permeable ROS scavenge and an active metabolite of Amifostine.
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

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Certificates of Analysis (COA)

Lot/Batch Number
0000296827
0000296827
0000230108
0000174524
0000180746

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Radiotherapy alone, versus radiotherapy with amifostine 3 times weekly, versus radiotherapy with amifostine 5 times weekly: A prospective randomized study in squamous cell head and neck cancer
Jellema AP, et al.
Cancer, 107(3), 544-553 (2006)
Caroline Prouillac et al.
Free radical biology & medicine, 46(8), 1139-1148 (2009-05-15)
Thiol and aminothiol compounds are among the most efficient chemical radioprotectors. To increase their efficiency, we synthesized two new classes of thiol and aminothiol compounds derived from benzothiazole (T1, T2, AM1, AM2) and thiadiazole (T3, T4, AM3) structures. We examined
Amifostine: the first selective-target and broad-spectrum radioprotector
Kouvaris JR, et al.
Oncologist, 12(6), 738-747 (2007)
Trevor McKibbin et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 16(3), 1049-1057 (2010-01-28)
We evaluated the pharmacokinetics of amifostine and WR1065 in pediatric patients with newly diagnosed medulloblastoma to assess the influence of patient covariates, including demographics, clinical characteristics, and genetic polymorphisms, on amifostine and WR1065 pharmacokinetic parameters. We assessed the pharmacokinetics of
Abdul-Kader Souid et al.
Molecular pharmaceutics, 3(3), 307-321 (2006-06-06)
Doxorubicin executes topoisomerase II mediated apoptosis, a process known to result in mitochondrial dysfunction, such as the leakage of cytochrome c and the opening of mitochondrial permeability transition pores (PTP). To further define the effects of doxorubicin on cell metabolism
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