Amifostine trihydrate
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MedKoo CAT#: 100050

CAS#: 112901-68-5 (trihydrate)

Description: Amifostine is a phosphorylated aminosulfhydryl compound. After dephosphorylation of amifostine by alkaline phosphatase to an active free sulfhydryl (thiol) metabolite, the thiol metabolite binds to and detoxifies cytotoxic platinum-containing metabolites of cisplatin and scavenges free radicals induced by cisplatin and ionizing radiation. The elevated activity of this agent in normal tissues results from both the relative abundance of alkaline phosphatase in normal tissues and the greater vascularity of normal tissues compared to tumor tissues.

Chemical Structure

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Amifostine trihydrate
CAS# 112901-68-5 (trihydrate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100050
Name: Amifostine trihydrate
CAS#: 112901-68-5 (trihydrate)
Chemical Formula: C5H21N2O6PS
Exact Mass: 0.00
Molecular Weight: 268.260
Elemental Analysis: C, 22.39; H, 7.89; N, 10.44; O, 35.78; P, 11.55; S, 11.95

Price and Availability

Size Price Availability Quantity
500mg USD 110 Ready to ship
1g USD 190 Ready to ship
2g USD 325 Ready to ship
5g USD 700 Ready to ship
10g USD 1250 Ready to ship
20g USD 2250 Ready to ship
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Related CAS #: 20537-88-6 (free)   112901-68-5 (trihydrate)   59178-37-9 (sodium)   63717-27-1 (monohydrate)  

Synonym: WR2721; WR-2721; WR 2721; YM08310; YM-08310; YM 08310; Aminopropylaminoethylthiophosphoric Acid; ethiofos; gammaphos. US brand name: Ethyol. Abbreviation: APAETP.

IUPAC/Chemical Name: S-(2-((3-aminopropyl)amino)ethyl) O,O-dihydrogen phosphorothioate trihydrate

InChi Key: TXQPXJKRNHJWAX-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: OP(O)(SCCNCCCN)=O.[H]O[H].[H]O[H].[H]O[H]

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Slightly soluble in DMSO, soluble in water (5mg/mL).

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be fromulated in water.

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related: 112901-68-5 (Amifostine trihydrate) 20537-88-6 (Amifostine). Accordiong to http://en.wikipedia.org/wiki/Amifostine, amifostine is a cytoprotective adjuvant used in cancer chemotherapy involving DNA-binding chemotherapeutic agents. Also commonly known as WR-1065 in its active form. It is marketed by MedImmune under the trade name Ethyol. Amifostine is used therapeutically to reduce the incidence of neutropenia-related fever and infection induced by DNA-binding chemotherapeutic agents including alkylating agents (e.g. cyclophosphamide) and platinum-containing agents (e.g. cisplatin). It is also used to decrease the cumulative nephrotoxicity associated with platinum-containing agents. Amifostine is also indicated to reduce the incidence of xerostomia in patients undergoing radiotherapy for head and neck cancer. Amifostine was originally indicated to reduce the cumulative renal toxicity from cisplatin in non-small cell lung cancer. 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 for non-small cell lung cancer was withdrawn in 2005. Amifostine is an organic thiophosphate prodrug which is hydrolysed in vivo by alkaline phosphatase to the active cytoprotective thiol metabolite. 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. Amifostine can only be administered intravenously, after reconstitution with normal saline. Infusions lasting less than 15 minutes decrease the risk of adverse effects. The patient should be well-hydrated before administration.     Amifostine is a white crystalline powder which is freely soluble in water. Its empirical formula is C5H15N2O3PS and it has a molecular weight of 214.22. ETHYOL is the trihydrate form of amifostine and is supplied as a sterile lyophilized powder requiring reconstitution for intravenous infusion. Each single-use 10 mL vial contains 500 mg of amifostine on the anhydrous basis. Amifostine is a white crystalline powder which is freely soluble in water. Its empirical formula is C5H15N2O3PS and it has a molecular weight of 214.22. ETHYOL is the trihydrate form of amifostine and is supplied as a sterile lyophilized powder requiring reconstitution for intravenous infusion. Each single-use 10 mL vial contains 500 mg of amifostine on the anhydrous basis.

Biological target: Amifostine trihydrate is a hypoxia-inducible factor-α1 (HIF-α1) and p53 inducer.
In vitro activity: As depicted in Figure 2(a), there was no difference in the proliferation of cells treated with 0 M, 10−7 M, and 10−9 M AMI (Amifostine). However, the proliferation of cells in the group treated with 10−5 M AMI was significantly inhibited on the seventh day of the experiment. Therefore, AMI was administered at a concentration of 10−7 M in the subsequent experiments. Figure 2(b) demonstrates that the proliferation of BMSCs in group C was significantly inhibited in comparison to that of group A (P < 0.05) on the fifth and seventh days of the experiment. The proliferation of cells on the fifth and seventh days was much higher in the group that received 2 Gy radiation in conjunction with AMI than the group that received 2 Gy radiation alone (P < 0.05). Reference: Stem Cells Int. 2019; 2019: 8749090. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6343176/
In vivo activity: Strikingly, amifostine treatment markedly reduced neurological deficits and appeared to be dose-dependent (Fig. 1A). The percentage of brain infarct area was obviously enlarged in the MCAO/R group, while amifostine treatment apparently diminished it, particularly in the MCAO/R + H group (Fig. 1C). Also, there was a significant increase in brain water content of MCAO/R mice, which could be relieved by amifostine treatment (Fig. 1D). Furthermore, H&E staining displayed the histopathological and morphological alteration of hippocampus CA1 (Fig. 1E). In the sham group, the neuron cell structure was normal, the edge was clear, and the nuclei and intercellular substance were stained evenly. In contrast, the neurons in the MCAO/R group exhibited a disordered arrangement with obvious oedema and necrosis. Importantly, treatment of amifostine significantly attenuated the extent of brain oedema and neuronal necrosis. By using Nissl staining, the results showed that the number of stained Nissl’s bodies was significantly declined in mice of the MCAO/R group. After amifostine treatment, its number was increased significantly (Fig. 1F). These findings provided evidence that amifostine could prevent brain failure caused by I/R. Reference: Folia Neuropathol. 2020;58(4):334-346. https://pubmed.ncbi.nlm.nih.gov/33480238/

Preparing Stock Solutions

The following data is based on the product molecular weight 268.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Huang B, He T, Yao Q, Zhang L, Yao Y, Tang H, Gong P. Amifostine Suppresses the Side Effects of Radiation on BMSCs by Promoting Cell Proliferation and Reducing ROS Production. Stem Cells Int. 2019 Jan 9;2019:8749090. doi: 10.1155/2019/8749090. PMID: 30728842; PMCID: PMC6343176. 2. Wang HT, Yang B, Hu B, Chi XH, Luo LL, Yang HQ, Lang XL, Geng J, Qiao CX, Li Y, Wu XX, Zhu HL, Lv M, Lu XC. The effect of amifostine on differentiation of the human megakaryoblastic Dami cell line. Cancer Med. 2016 Aug;5(8):2012-21. doi: 10.1002/cam4.759. Epub 2016 May 26. PMID: 27228575; PMCID: PMC4884634. 3. Cheng H, Lv M, Mi R, Xue G. Amifostine ameliorates cerebral ischaemia-reperfusion injury via p38-mediated oxidative stress and mitochondrial dysfunction. Folia Neuropathol. 2020;58(4):334-346. doi: 10.5114/fn.2020.102436. PMID: 33480238. 4. Pereira AF, Lino JA, Alves BWF, Lisboa MRP, Pontes RB, Leite CAVG, Nogueira RB, Lima-Júnior RCP, Vale ML. Amifostine protects from the peripheral sensory neuropathy induced by oxaliplatin in mice. Braz J Med Biol Res. 2020 Sep 18;53(11):e10263. doi: 10.1590/1414-431X202010263. PMID: 32965323; PMCID: PMC7510240.
In vitro protocol: 1. Huang B, He T, Yao Q, Zhang L, Yao Y, Tang H, Gong P. Amifostine Suppresses the Side Effects of Radiation on BMSCs by Promoting Cell Proliferation and Reducing ROS Production. Stem Cells Int. 2019 Jan 9;2019:8749090. doi: 10.1155/2019/8749090. PMID: 30728842; PMCID: PMC6343176. 2. Wang HT, Yang B, Hu B, Chi XH, Luo LL, Yang HQ, Lang XL, Geng J, Qiao CX, Li Y, Wu XX, Zhu HL, Lv M, Lu XC. The effect of amifostine on differentiation of the human megakaryoblastic Dami cell line. Cancer Med. 2016 Aug;5(8):2012-21. doi: 10.1002/cam4.759. Epub 2016 May 26. PMID: 27228575; PMCID: PMC4884634.
In vivo protocol: 1. Cheng H, Lv M, Mi R, Xue G. Amifostine ameliorates cerebral ischaemia-reperfusion injury via p38-mediated oxidative stress and mitochondrial dysfunction. Folia Neuropathol. 2020;58(4):334-346. doi: 10.5114/fn.2020.102436. PMID: 33480238. 2. Pereira AF, Lino JA, Alves BWF, Lisboa MRP, Pontes RB, Leite CAVG, Nogueira RB, Lima-Júnior RCP, Vale ML. Amifostine protects from the peripheral sensory neuropathy induced by oxaliplatin in mice. Braz J Med Biol Res. 2020 Sep 18;53(11):e10263. doi: 10.1590/1414-431X202010263. PMID: 32965323; PMCID: PMC7510240.

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2: King M, Joseph S, Albert A, Thomas TV, Nittala MR, Woods WC, Vijayakumar S, Packianathan S. Use of Amifostine for Cytoprotection during Radiation Therapy: A Review. Oncology. 2020;98(2):61-80. doi: 10.1159/000502979. Epub 2019 Dec 17. PMID: 31846959.


3: Bahat Z, Cobanoglu U, Ulku C, Kalyoncu Nİ, Caner Karahan S, Yavuz MN. Could Amifostine Prevent Experimental Radiotherapy-Induced Acute Pericarditis? Asian Pac J Cancer Prev. 2022 Sep 1;23(9):3209-3213. doi: 10.31557/APJCP.2022.23.9.3209. PMID: 36172686; PMCID: PMC9810295.


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10: Yu X, Li M, Zhu L, Li J, Zhang G, Fang R, Wu Z, Jin Y. Amifostine-loaded armored dissolving microneedles for long-term prevention of ionizing radiation- induced injury. Acta Biomater. 2020 Aug;112:87-100. doi: 10.1016/j.actbio.2020.05.025. Epub 2020 May 23. Erratum in: Acta Biomater. 2022 Nov;153:630-631. PMID: 32450231.


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16: Gezer A, Karadag-Sari E. The role of amifostine in preventing radiotherapy induced testicular tissue damage in rats. Biotech Histochem. 2022 Apr;97(3):215-221. doi: 10.1080/10520295.2021.1933178. Epub 2021 Jun 1. PMID: 34058938.


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