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A5922

Sigma-Aldrich

Amifostine trihydrate

≥97% (TLC), powder

Synonym(s):

2-(3-Aminopropyl)aminoethyl phosphorothioate, WR2721

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About This Item

Empirical Formula (Hill Notation):
C5H15N2O3PS · 3 H2O
CAS Number:
112901-68-5
Molecular Weight:
268.27
MDL number:
MFCD00453866
UNSPSC Code:
12352200
PubChem Substance ID:
24278231
NACRES:
NA.77

Quality Level

200

Assay

≥97% (TLC)

form

powder

storage temp.

2-8°C

SMILES string

OP(SCCNCCCN)(O)=O.O.O.O

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

InChI key

TXQPXJKRNHJWAX-UHFFFAOYSA-N

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Application

Amifostine may provide renal protection during PRRT using somatostatin analogs by mitigating radiation damage and reducing the absorbed kidney radiation dose. Amifostine remediates the degenerative effects of radiation on the mineralization capacity of the murine mandible.

Biochem/physiol Actions

Radioprotective agent. Selectively protects normal tissues from the damaging effects of anti-neoplastic radiation therapy. Selectivity is due to preferential uptake by normal tissues and subsequent metabolic activation to 2-(3-aminopropyl)aminoethanethiol.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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R L Capizzi et al.
Cancer, 72(11 Suppl), 3495-3501 (1993-12-01)
Amifostine (US Bioscience, West Conshohocken, PA; Ethyol, WR-2721), a phosphorylated thiol developed by the United States Army as a protective agent for military personnel in the event of nuclear warfare, has shown protection of normal tissues from the cytotoxic effects
David A Oʼdonovan et al.
Plastic and reconstructive surgery, 129(4), 636e-645e (2012-03-30)
The authors previously established an animal model of radiation-induced craniofacial bone growth inhibition and demonstrated the effectiveness of cytoprotection in preserving growth using amifostine, but the mechanism is unclear. The objective of this study was to investigate the acute and
Catherine N Tchanque-Fossuo et al.
Bone, 52(2), 712-717 (2012-08-14)
Adjuvant radiotherapy in the management of head and neck cancer remains severely debilitating. Fortunately, newly developed agents aimed at decreasing radiation-induced damage have shown great promise. Amifostine (AMF) is a compound, which confers radio-protection to the exposed normal tissues, such
Marleen Melis et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 53(5), 749-753 (2012-04-13)
Megalin-mediated renal retention of radiolabeled somatostatin analogs may lead to nephrotoxicity during peptide receptor radionuclide therapy (PRRT). The cytoprotective agent amifostine protected rats from long-term nephrotoxicity after PRRT with (177)Lu-DOTA,Tyr(3)-octreotate. This study describes the direct effect of amifostine on kidney
C M Spencer et al.
Drugs, 50(6), 1001-1031 (1995-12-01)
Amifostine (WR-2721) was originally developed as a radioprotective agent. In animals, it protects normal tissues from the damaging effects of irradiation and, as shown in more recent studies, of several cytotoxic agents. Protection of tumours is generally reduced compared with
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