[CAS NO. 20537-88-6] Amifostine
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PRODUCTS SPECIFICATIONS [20537-88-6]
Catalog
HY-B0639
Brand
MCE
CAS
20537-88-6
DESCRIPTION [20537-88-6]
Overview
| MDL | MFCD00233058 |
|---|---|
| Molecular Weight | 214.22 |
| Molecular Formula | C5H15N2O3PS |
| SMILES | OP(SCCNCCCN)(O)=O |
For research use only. We do not sell to patients.
1 Publications Citing Use of MCE
Summary
Amifostine (WR2721) is a broad-spectrum cytoprotective agent and a radioprotector. Amifostine selectively protects normal tissues from damage caused by radiation and chemotherapy. Amifostine is potent hypoxia-inducible factor-α1 (HIF-α1) and p53 inducer. Amifostine protects cells from damage by scavenging oxygen-derived free radicals. Amifostine reduces renal toxicity and has antiangiogenic action [1] [2] [3] [4] .
In Vitro
Amifostine (0.78125-100 μM, 24 h) reduces tert-Butyl hydroperoxide (TBHP)-induced cell damage in a dose-dependent manner and significantly reduces H9c2 cells apoptosis at a concentration of 100 μM
[5]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Amifostine (i.v., 400 mg/kg, 4 h) has a protective effect against myocardial I/R injury in male C57BL/6 mice
[5]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| Animal Model: | Male C57BL/6 mice with myocardial I/R injury [5] |
| Dosage: | 400 mg/kg |
| Administration: | Intravenous injection; 4 hours |
| Result: |
Attenuated cardiomyocyte apoptosis and reduced the production of I/R-induced ROS.
Significantly reduced the expression of cleaved caspase 3 and Bax while enhanced the expression of SOD1, SOD2 and Bcl2. Significantly increased SOD activity and reduced MDA levels. |
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date | Phase |
|---|---|---|---|---|
| NCT00003927 | City of Hope Medical Center|National Cancer Institute (NCI) |
Breast Cancer
|
May 18, 1999 | Phase 1 |
| NCT00003068 | University of Arizona|National Cancer Institute (NCI) |
Breast Cancer|Drug+Agent Toxicity by Tissue+Organ
|
June 1997 | Phase 2 |
| NCT00004264 | University of Wisconsin, Madison|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Lung Cancer
|
July 1997 | Phase 1|Phase 2 |
| NCT00003225 | Jonsson Comprehensive Cancer Center|ALZA |
Colorectal Cancer
|
July 1997 | Phase 1|Phase 2 |
| NCT00098683 | Children´s Oncology Group|National Cancer Institute (NCI) |
Myelodysplastic Syndromes|Myelodysplastic+Myeloproliferative Neoplasms
|
January 2005 | Phase 2 |
| NCT00003407 | Rush University Medical Center|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Leukemia|Myelodysplastic Syndromes|Neutropenia
|
April 1998 | Phase 2 |
| NCT01288625 | Sun Pharmaceutical Industries Limited |
Oral Mucositis|Stomatitis
|
Phase 4 | |
| NCT00052884 | Eastern Cooperative Oncology Group|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Multiple Myeloma and Plasma Cell Neoplasm
|
October 2003 | Phase 1 |
| NCT00003089 | Sidney Kimmel Cancer Center at Thomas Jefferson University|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Lung Cancer
|
July 1997 | Phase 2 |
| NCT00004176 | Washington University School of Medicine|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Lung Cancer|Radiation Toxicity
|
October 1998 | Phase 2 |
| NCT00003580 | University of Tennessee|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Head and Neck Cancer|Oral Complications|Radiation Toxicity
|
June 1998 | Phase 2 |
| NCT00081315 | MedImmune LLC |
Esophagitis|Pneumonitis|Non-Small Cell Lung Carcinoma
|
November 2003 | Phase 2 |
| NCT00409331 | M.D. Anderson Cancer Center|MedImmune LLC |
Head and Neck Cancer
|
December 2006 | Phase 2 |
| NCT00040365 | National Cancer Institute (NCI)|National Institutes of Health Clinical Center (CC) |
Prostatic Neoplasms
|
June 2002 | Phase 2 |
| NCT00003681 | European Organisation for Research and Treatment of Cancer - EORTC|National Cancer Institute (NCI) |
Anemia|Myelodysplastic Syndromes
|
August 1998 | Phase 2 |
| NCT00025298 | European Organisation for Research and Treatment of Cancer - EORTC |
Drug+Agent Toxicity by Tissue+Organ|Head and Neck Cancer|Oral Complications|Radiation Toxicity
|
July 2001 | Phase 2 |
| NCT00003123 | Providence Hospital|National Cancer Institute (NCI) |
Myelodysplastic Syndromes
|
August 1997 | Phase 2 |
| NCT01586117 | Cancer Institute and Hospital, Chinese Academy of Medical Sciences |
Rectal Cancer
|
February 2012 | Phase 2 |
| NCT00095927 | Dana-Farber Cancer Institute|National Cancer Institute (NCI)|MedImmune LLC|AstraZeneca |
Chemotherapeutic Agent Toxicity|Head and Neck Cancer|Mucositis|Radiation Toxicity|Xerostomia
|
May 2003 | Phase 2 |
| NCT00217438 | Fred Hutchinson Cancer Center|National Cancer Institute (NCI) |
Refractory Multiple Myeloma|Stage II Multiple Myeloma|Stage III Multiple Myeloma
|
July 2005 | Phase 3 |
| NCT00003211 | St. Jude Children´s Research Hospital|National Cancer Institute (NCI) |
Brain and Central Nervous System Tumors
|
October 1996 | Phase 2 |
| NCT00003144 | NYU Langone Health|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Unspecified Adult Solid Tumor, Protocol Specific
|
August 1997 | Phase 1 |
| NCT00006012 | Alliance for Clinical Trials in Oncology|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Lung Cancer|Radiation Toxicity
|
February 2001 | Phase 1|Phase 2 |
| NCT00003307 | University of Arizona|National Cancer Institute (NCI) |
Prostate Cancer|Radiation Toxicity
|
March 1998 | Phase 2 |
| NCT01998529 | M.D. Anderson Cancer Center |
Lung Cancer
|
August 20, 2014 | Phase 1 |
| NCT00003415 | University of Arizona|National Cancer Institute (NCI) |
Leukemia|Myelodysplastic Syndromes
|
September 1998 | Phase 1|Phase 2 |
| NCT00003405 | Rush University Medical Center|National Cancer Institute (NCI) |
Leukemia
|
April 1998 | Phase 2 |
| NCT00137358 | University of Alabama at Birmingham|MedImmune LLC |
Cervical Cancer
|
Phase 1 | |
| NCT00003193 | Massachusetts General Hospital |
Head and Neck Cancer|Oral Complications
|
January 1998 | Phase 1|Phase 2 |
| NCT00058071 | Gynecologic Oncology Group|National Cancer Institute (NCI)|GOG Foundation |
Gestational Trophoblastic Tumor|Neurotoxicity|Peripheral Neuropathy|Unspecified Adult Solid Tumor, Protocol Specific
|
March 2003 | Phase 3 |
| NCT00136474 | Dana-Farber Cancer Institute|Brigham and Women´s Hospital|Beth Israel Deaconess Medical Center|MedImmune LLC |
Lymphoma|Hodgkin´s Disease|Non-Hodgkin´s Lymphoma
|
May 2003 | Phase 2 |
| NCT00601198 | University of Cincinnati|MedImmune LLC|AstraZeneca |
Colorectal Cancer
|
October 2006 | Phase 2 |
| NCT00003827 | ALZA|National Cancer Institute (NCI) |
Leukemia|Myelodysplastic Syndromes
|
January 1999 | Phase 2 |
| NCT00003582 | University of Miami |
Carcinoma of Unknown Primary|Head and Neck Cancer
|
May 1988 | Phase 1|Phase 2 |
| NCT00503776 | Vanderbilt-Ingram Cancer Center|National Cancer Institute (NCI) |
Dysphagia|Head and Neck Cancer|Mucositis|Xerostomia
|
January 2006 | Phase 2 |
| NCT00003251 | University of Illinois at Chicago|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Head and Neck Cancer|Radiation Toxicity
|
December 1997 | Phase 1|Phase 2 |
| NCT00130143 | The Dale & Frances Hughes Cancer Center|MedImmune LLC |
Head and Neck Cancer|Lung Cancer
|
June 2003 | Not Applicable |
| NCT01762514 | Sun Yat-sen University|Dalian Merro Pharmaceutical Co. Ltd |
Nasopharyngeal Neoplasms|Salivary Gland Diseases|Bone Marrow Diseases|Mucositis
|
January 2013 | Phase 2 |
| NCT00003313 | Radiation Therapy Oncology Group|National Cancer Institute (NCI)|NRG Oncology |
Drug+Agent Toxicity by Tissue+Organ|Lung Cancer|Oral Complications|Radiation Toxicity
|
September 1998 | Phase 3 |
| NCT00003252 | Rush North Shore Medical Center|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Unspecified Adult Solid Tumor, Protocol Specific
|
December 1997 | Phase 4 |
| NCT00003268 | Sidney Kimmel Cancer Center at Thomas Jefferson University|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Leukemia
|
January 1998 | Phase 1 |
| NCT00002643 | National Cancer Institute (NCI)|Children´s Cancer Group |
Neutropenia|Sarcoma
|
April 1995 | Phase 2 |
| NCT00004919 | National Cancer Institute (NCI) |
Unspecified Childhood Solid Tumor, Protocol Specific
|
December 1999 | Phase 1 |
| NCT00003555 | State University of New York - Upstate Medical University|National Cancer Institute (NCI) |
Unspecified Adult Solid Tumor, Protocol Specific
|
July 1998 | Phase 1 |
| NCT00003136 | University of Chicago |
Ovarian Cancer|Primary Peritoneal Cavity Cancer
|
December 1996 | Phase 1|Phase 2 |
| NCT00003583 | University of Florida|National Cancer Institute (NCI) |
Drug+Agent Toxicity by Tissue+Organ|Lung Cancer|Radiation Toxicity
|
June 1997 | Phase 2 |
| NCT00003624 | Gynecologic Oncology Group|National Cancer Institute (NCI)|GOG Foundation |
Cervical Cancer|Endometrial Cancer|Fallopian Tube Cancer|Neurotoxicity|Ovarian Cancer|Primary Peritoneal Cavity Cancer|Sarcoma
|
December 1998 | Phase 2 |
| NCT00003811 | Children´s Oncology Group|National Cancer Institute (NCI) |
Childhood Germ Cell Tumor|Drug+Agent Toxicity by Tissue+Organ|Extragonadal Germ Cell Tumor|Ovarian Cancer
|
April 2000 | Phase 2 |
| NCT00012012 | Radiation Therapy Oncology Group|National Cancer Institute (NCI) |
Cervical Cancer|Radiation Toxicity
|
August 2001 | Phase 1|Phase 2 |
| NCT00003994 | Children´s Oncology Group|National Cancer Institute (NCI) |
Childhood Hepatoblastoma|Recurrent Childhood Liver Cancer|Stage I Childhood Liver Cancer
|
March 1999 | Phase 3 |
| NCT00003657 | Dana-Farber Cancer Institute|National Cancer Institute (NCI) |
Bladder Cancer|Brain and Central Nervous System Tumors|Carcinoma of Unknown Primary|Extragonadal Germ Cell Tumor|Head and Neck Cancer|Kidney Cancer|Lung Cancer|Ovarian Cancer|Sarcoma|Testicular Germ Cell Tumor|Unspecified Adult Solid Tumor, Protocol Specific
|
July 1998 | Phase 2 |
| NCT00004166 | Northwestern University|National Cancer Institute (NCI) |
Ovarian Cancer|Quality of Life
|
October 1999 | Phase 3 |
| NCT00318890 | University of Alabama at Birmingham|Aventis Pharmaceuticals |
Cancer of Head and Neck|Head Cancer|Head and Neck Cancer|Neck Cancer|Neck Neoplasms
|
October 2002 | Phase 1|Phase 2 |
| NCT00003127 | Southwest Oncology Group|National Cancer Institute (NCI) |
Endometrial Cancer
|
February 1998 | Phase 2 |
| NCT00003425 | University of Kentucky |
Breast Cancer|Leukemia|Lymphoma|Neuroblastoma|Ovarian Cancer|Sarcoma|Unspecified Adult Solid Tumor, Protocol Specific
|
December 1997 | Phase 1|Phase 2 |
| NCT00078845 | M.D. Anderson Cancer Center|National Cancer Institute (NCI) |
Breast Cancer|Lung Cancer|Neurotoxicity|Ovarian Cancer|Prostate Cancer|Unspecified Adult Solid Tumor, Protocol Specific
|
May 2004 | Phase 2 |
| NCT00270790 | Mohan Suntharalingam|MedImmune LLC|University of Maryland, Baltimore |
Head and Neck Cancer
|
May 2002 | Phase 2 |
| NCT00004036 | The Cleveland Clinic|National Cancer Institute (NCI) |
Chronic Myeloproliferative Disorders|Drug+Agent Toxicity by Tissue+Organ|Leukemia|Lymphoma|Multiple Myeloma and Plasma Cell Neoplasm|Myelodysplastic Syndromes|Precancerous Condition|Unspecified Adult Solid Tumor, Protocol Specific
|
November 1997 | Phase 1 |
| NCT00158041 | Mt. Sinai Medical Center, Miami|MedImmune LLC |
Head and Neck Cancer|Lung Cancer|Lymphoma
|
January 2002 | Phase 4 |
| NCT00286611 | University of Iowa |
Cancer
|
October 2004 | |
| NCT00003143 | Jonsson Comprehensive Cancer Center |
Lymphoma
|
November 1997 | Phase 2 |
| NCT00006127 | Dana-Farber Cancer Institute|Office of Rare Diseases (ORD) |
Fanconi´s Anemia
|
April 2000 | Phase 1 |
| NCT03702985 | Fudan University |
Locally Advanced Rectal Cancer
|
May 28, 2018 | Phase 2 |
| NCT00571298 | Brigham and Women´s Hospital|Dana-Farber Cancer Institute |
Malignant Pleural Mesothelioma
|
November 2007 | Phase 1 |
| NCT00274937 | Children´s Oncology Group|National Cancer Institute (NCI) |
Stage I Nasopharyngeal Keratinizing Squamous Cell Carcinoma AJCC v7|Stage I Nasopharyngeal Undifferentiated Carcinoma AJCC v7|Stage II Nasopharyngeal Keratinizing Squamous Cell Carcinoma AJCC v7|Stage II Nasopharyngeal Undifferentiated Carcinoma AJCC v7|Stage III Nasopharyngeal Keratinizing Squamous Cell Carcinoma AJCC v7|Stage III Nasopharyngeal Undifferentiated Carcinoma AJCC v7|Stage IV Nasopharyngeal Keratinizing Squamous Cell Carcinoma AJCC v7|Stage IV Nasopharyngeal Undifferentiated Carcinoma AJCC v7
|
February 20, 2006 | Phase 3 |
| NCT00003072 | University of California, San Francisco |
Lung Cancer|Neurotoxicity|Ovarian Cancer
|
May 1997 | Phase 2 |
| NCT00006105 | University of Chicago|National Cancer Institute (NCI) |
Bladder Cancer|Drug+Agent Toxicity by Tissue+Organ
|
June 2000 | Phase 2 |
| NCT00003294 | Roswell Park Cancer Institute|National Cancer Institute (NCI) |
Leukemia|Lymphoma|Unspecified Adult Solid Tumor, Protocol Specific
|
May 1997 | Phase 1 |
| NCT00003048 | M.D. Anderson Cancer Center|National Cancer Institute (NCI) |
Myelodysplastic Syndromes
|
June 5, 1997 | Phase 2 |
| NCT00003926 | Masonic Cancer Center, University of Minnesota |
Brain and Central Nervous System Tumors|Childhood Germ Cell Tumor|Chordoma|Kidney Cancer|Liver Cancer|Neuroblastoma|Ovarian Cancer|Retinoblastoma|Sarcoma
|
November 1998 | Phase 1 |
| NCT00003269 | Scripps Health |
Breast Cancer|Drug+Agent Toxicity by Tissue+Organ|Lung Cancer|Lymphoma|Ovarian Cancer|Unspecified Adult Solid Tumor, Protocol Specific
|
February 1998 | Phase 2 |
| NCT00005598 | University of Michigan Rogel Cancer Center|National Cancer Institute (NCI) |
Myelodysplastic Syndromes
|
October 2000 | Phase 2 |
| NCT05167370 | Children´s Hospital Medical Center, Cincinnati |
Solid Tumors|Brain Tumors
|
December 13, 2010 | Phase 2 |
| NCT00003777 | Abramson Cancer Center of the University of Pennsylvania |
Head and Neck Cancer
|
December 1998 | Phase 2 |
| NCT01364259 | Stanford University |
Trigeminal Neuralgia
|
September 2008 | Phase 3 |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
In Vitro:
H 2 O : 100 mg/mL ( 466.81 mM ; Need ultrasonic)
DMF : 1 mg/mL ( 4.67 mM ; Need ultrasonic)
DMSO : < 1 mg/mL (ultrasonic) (insoluble or slightly soluble)
Preparing
Stock Solutions
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 4.6681 mL | 23.3405 mL | 46.6810 mL |
| 5 mM | 0.9336 mL | 4.6681 mL | 9.3362 mL |
| 10 mM | 0.4668 mL | 2.3340 mL | 4.6681 mL |
*
Please refer to the solubility information to select the appropriate solvent.
In Vivo:
-
1.
Add each solvent one by one: PBS
Solubility: 100 mg/mL (466.81 mM); Clear solution; Need ultrasonic and warming and heat to 60°C
*
All of the co-solvents are available by MCE.
References
- [1] Kouvaris, J.R., V.E. Kouloulias, and L.J. Vlahos, Amifostine: the first selective-target and broad-spectrum radioprotector. Oncologist, 2007. 12(6): p. 738-47.
- [2] D Maurici, et al. Amifostine (WR2721) restores transcriptional activity of specific p53 mutant proteins in a yeast functional assay. Oncogene. 2001 Jun 14;20(27):3533-40.
- [3] Efstathia Giannopoulou, et al. Amifostine inhibits angiogenesis in vivo. J Pharmacol Exp Ther. 2003 Feb;304(2):729-37.
- [4] Michael I Koukourakis, et al. Amifostine induces anaerobic metabolism and hypoxia-inducible factor 1 alpha. Cancer Chemother Pharmacol. 2004 Jan;53(1):8-14.
- [5] Shao-Ze Wu, et al. Amifostine Pretreatment Attenuates Myocardial Ischemia/Reperfusion Injury by Inhibiting Apoptosis and Oxidative Stress. Oxid Med Cell Longev. 2017;2017:4130824.
Synonyms
Ethanethiol, 2-[(3-aminopropyl)amino]-, 1-(dihydrogen phosphate)
Phosphorothioic acid, S-[2-[(3-aminopropyl)amino]ethyl] ester
Ethanethiol, 2-[(3-aminopropyl)amino]-, dihydrogen phosphate (ester)
WR 2721C
WR 2721
S-[N-(3-Aminopropyl)-2-aminoethyl] dihydrogen thiophosphate
Gammaphos
Aminopropylaminoethyl thiophosphate
S-[2-(3-Aminopropylamino)ethyl] phosphorothioate
S-[2-[(3-Aminopropyl)amino]ethyl] dihydrogen phosphorothioate
YM 08310
2-(3-Aminopropylamino)ethyl thiophosphate
Ethiofos
NSC 296961
Amifostine
Ethyol
S 8744
SAPEP
([2-[(3-Aminopropyl)amino]ethyl]sulfanyl)phosphonic acid
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