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)

Theoretical Analysis

MedKoo Cat#: 100050
Name: Amifostine trihydrate
CAS#: 112901-68-5 (trihydrate)
Chemical Formula: C5H21N2O6PS
Exact Mass:
Molecular Weight: 268.26
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
500.0mg USD 110.0 Same day
1.0g USD 190.0 Same Day
2.0g USD 350.0 Same Day
5.0g USD 750.0 Same Day
10.0g USD 1350.0 Same Day
20.0g USD 2350.0 Same Day
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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

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

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1: Duval M, Daniel SJ. Meta-analysis of the efficacy of amifostine in the prevention of cisplatin ototoxicity. J Otolaryngol Head Neck Surg. 2012 Oct;41(5):309-15. Review. PubMed PMID: 23092832.

2: Nicolatou-Galitis O, Sarri T, Bowen J, Di Palma M, Kouloulias VE, Niscola P, Riesenbeck D, Stokman M, Tissing W, Yeoh E, Elad S, Lalla RV; Mucositis Study Group of the Multinational Association of Supportive Care in Cancer/International Society of Oral Oncology (MASCC/ISOO). Systematic review of amifostine for the management of oral mucositis in cancer patients. Support Care Cancer. 2013 Jan;21(1):357-64. doi: 10.1007/s00520-012-1613-6. Epub 2012 Oct 3. Review. PubMed PMID: 23052919.

3: Ma C, Xie J, Jiang Z, Wang G, Zuo S. Does amifostine have radioprotective effects on salivary glands in high-dose radioactive iodine-treated differentiated thyroid cancer. Eur J Nucl Med Mol Imaging. 2010 Aug;37(9):1778-85. doi: 10.1007/s00259-009-1368-6. Epub 2010 Feb 4. Review. PubMed PMID: 20130857.

4: Dang YH, Li W, Yang B, Zhu HL, Huang Y. [Mechanism and problem of amifostine in treating myelodysplastic syndromes]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2009 Dec;17(6):1597-601. Review. Chinese. PubMed PMID: 20030955.

5: Ma C, Xie J, Chen Q, Wang G, Zuo S. Amifostine for salivary glands in high-dose radioactive iodine treated differentiated thyroid cancer. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD007956. doi: 10.1002/14651858.CD007956.pub2. Review. PubMed PMID: 19821441.

6: Marcu LG. The role of amifostine in the treatment of head and neck cancer with cisplatin-radiotherapy. Eur J Cancer Care (Engl). 2009 Mar;18(2):116-23. doi: 10.1111/j.1365-2354.2008.01032.x. Review. PubMed PMID: 19267726.

7: Mell LK, Movsas B. Pharmacologic normal tissue protection in clinical radiation oncology: focus on amifostine. Expert Opin Drug Metab Toxicol. 2008 Oct;4(10):1341-50. doi: 10.1517/17425255.4.10.1341 . Review. PubMed PMID: 18798703.

8: Praetorius NP, Mandal TK. Alternate delivery route for amifostine as a radio-/chemo-protecting agent. J Pharm Pharmacol. 2008 Jul;60(7):809-15. doi: 10.1211/jpp.60.7.0001. Review. PubMed PMID: 18549666.

9: Kouloulias VE, Kouvaris JR. Cytoprotective efficacy of amifostine against radiation- induced rectal toxicity: objective and subjective grading scales for radiomucositis. Molecules. 2008 Apr 18;13(4):892-903. Review. PubMed PMID: 18463591.

10: Kouvaris JR, Kouloulias VE, Vlahos LJ. Amifostine: the first selective-target and broad-spectrum radioprotector. Oncologist. 2007 Jun;12(6):738-47. Review. PubMed PMID: 17602063.



Additional Information

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.