Phosphorylethanolamine
 | |
| Names | |
|---|---|
| IUPAC name
2-Aminoethyl dihydrogen phosphate | |
| Other names
Phosphoethanolamine; PHOS | |
| Identifiers | |
1071-23-4  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:17553 |
| ChEMBL | ChEMBL146972 |
| ChemSpider | 990 |
| DrugBank | DB01738  |
| ECHA InfoCard | 100.012.717 |
| MeSH | phosphorylethanolamine |
| PubChem | 1015 |
| UNII | 78A2BX7AEU |
| |
| |
| Properties | |
| C2H8NO4P | |
| Molar mass | 141.06 g·mol−1 |
| Appearance | White powder |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Phosphorylethanolamine or phosphoethanolamine is an ethanolamine derivative that is used to construct two different categories of phospholipids. One category termed a glycerophospholipid and the other a sphingomyelin, or more specifically within the sphingomyelin class, a sphingophospholipid. Phosphorylethanolamine is a polyprotic acid with two pKa values at 5.61 and 10.39.[1]
Research
Research is being conducted with Ehrlich ascites tumor cells in vitro to see if phosphoethanolamine could be used in cancer treatment.[2] In studies in rats, phosphorylethanolamine failed to stop the growth of tumors.[3][4]
As a potential drug, phosphorylethanolamine has never been evaluated in human clinical trials.[5][6]
Legality
There has been ongoing controversy and litigation in Brazil with regard to its use as a cancer treatment prior to approval by the National Health Surveillance Agency. In September 2015, administrators at the University of São Paulo attempted to prevent chemists at the São Carlos campus from continuing to unofficially manufacture, distribute, and promote the drug to cancer patients since it had not been tested in humans yet. In October 2015, several courts in Brazil ruled in favor of plaintiffs who wanted the right to try the compound. However, a state court overturned the lower courts' decision a month later. Jailson Bittencourt de Andrade, secretary for Brazil’s science and technology ministry, said the ministry plans to fund further research on the compound, but that it will be years before a determination can be made about phosphoethanolamine's safety and efficacy in humans.[7][8]
On April 14, 2016, a law was passed in Brazil allowing the use of synthetic phosphoethanolamine for cancer treatment,[9] despite opposition from the Brazilian Medical Association, the Brazilian Society of Clinical Oncology, and the regulatory agency ANVISA.[10] However, shortly after, the country's Supreme Court suspended the law.[11]
References
- ↑ Myller, AT; et al. (2010). "Preparation of aminofunctionalized TiO2 surfaces by binding of organophosphates". Applied Surface Science. 257: 1616.
- ↑ Ferreira, Adilson Kleber; Meneguelo, Renato; Pereira, Alexandre; Mendonça Filho, Otaviano R.; Chierice, Gilberto Orivaldo; Maria, Durvanei Augusto (2012-01-01). "Anticancer effects of synthetic phosphoethanolamine on Ehrlich ascites tumor: an experimental study". Anticancer Research. 32 (1): 95–104. ISSN 1791-7530. PMID 22213293.
- ↑ "Cancer Pill Fails. Again.". June 2, 2016.
- ↑ "Effectiveness of 'Cancer Pill' Disproved in New Test". June 1, 2016.
- ↑ "Drugs on demand". Nature. 527 (7579): 410. 2015. doi:10.1038/527410b.
- ↑ Pondé, Noam; De Azambuja, Evandro; Ades, Felipe (2016). "Phosphoethanolamine and the danger of unproven drugs". Ecancermedicalscience. 10. doi:10.3332/ecancer.2016.681.
- ↑ Heidi Ledford (24 November 2015). "Brazilian courts tussle over unproven cancer treatment". Nature. 527 (7579): 420. doi:10.1038/527420a.
- ↑ Escobar, H. (2016). "Brazil bill would legalize renegade cancer pill". Science. 352 (6281): 18. doi:10.1126/science.352.6281.18.
- ↑ Herton Escobar (14 April 2016). "Brazil president signs law legalizing renegade cancer pill". Sciencemag.com. doi:10.1126/science.aaf4126.
- ↑ Noam Pondé, Felipe Ades, Evandro de Azambuja (2016). "Threat posed by unproven drugs in medical oncology". Cancer Horizons. doi:10.1136/esmoopen-2016-000064 (inactive 2016-10-25).
- ↑ "Human tests start on controversial Brazil cancer pill". 25 July 2016.
