|Jmol-3D images||Image 1|
|Molar mass||128.94 g mol−1|
|Density||1.5634 g/cm3 (20 °C)|
|Melting point||9-11 °C, 282-284 K, 48-52 °F|
|Boiling point||194 °C, 467 K, 381 °F|
|Solubility in water||miscible|
|Solubility||miscible with ethanol, diethyl ether|
|Std enthalpy of
|S-phrases||(S1/2) S26 S45 S61|
|Related chloroacetic acids||Chloroacetic acid
|Related compounds||Acetic acid
| (verify) (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Dichloroacetic acid, often abbreviated DCA, is the chemical compound with formulaCHCl2COOH. It is an acid, an analogue of acetic acid, in which two of the three hydrogenatoms of the methyl group have been replaced by chlorine atoms. The salts and esters of dichloroacetic acid are called dichloroacetates. Salts of DCA have been studied as potential drugs because they inhibit the enzyme pyruvate dehydrogenase kinase.
Chemistry and occurrence
The chemistry of dichloroacetic acid is typical for halogenated organic acids. It is a member of the chloroacetic acids family. The dichloroacetate ion is produced when the acid is mixed with water. As an acid with a pKa of 1.35, pure dichloroacetic acid is verycorrosive and extremely destructive to tissues of the mucous membranes and upper respiratory tract.
DCA does not occur in nature. It is a trace product of the chlorination of drinking water and is produced by the metabolism of various chlorine-containing drugs or chemicals. DCA is typically prepared by the reduction of trichloroacetic acid.
Owing to the highly corrosive action of the acid, only the salts of dichloroacetic acid are used therapeutically, including its sodium and potassium salts, sodium dichloroacetate and potassium dichloroacetate.
The dichloroacetate ion stimulates the activity of the enzyme pyruvate dehydrogenase by inhibiting the enzyme pyruvate dehydrogenase kinase. Thus, it decreases lactateproduction by shifting the metabolism of pyruvate from fermentation towards oxidation in the mitochondria. This property has led to trials of DCA for the treatment of lactic acidosisin humans.
A randomized controlled trial in children with congenital lactic acidosis found that while DCA was well tolerated, it was ineffective in improving clinical outcomes. A separate trial of DCA in children with MELAS (a syndrome of inadequate mitochondrial function, leading to lactic acidosis) was halted early, as all 15 of the children receiving DCA experienced significant nerve toxicity without any evidence of benefit from the medication. A randomized controlled trial of DCA in adults with lactic acidosis found that while DCA lowered blood lactate levels, it had no clinical benefit and did not improve hemodynamicsor survival.
Thus, while early case reports and pre-clinical data suggested that DCA might be effective for lactic acidosis, subsequent controlled trials have found no clinical benefit of DCA in this setting. In addition, clinical trial subjects were incapable of continuing on DCA as a study medication owing to progressive toxicities.
Potential cancer applications
Cancer cells generally express increased glycolysis, because they rely on anaerobic respiration that occurs in the cytosol (lactic acid fermentation) rather than oxidative phosphorylation in the mitochondria for energy (the Warburg effect), as a result of hypoxia that exists in tumors and malfunctioning mitochondria. Usually dangerously damaged cells kill themselves via apoptosis, a mechanism of self-destruction that involves mitochondria, but this mechanism fails in cancer cells.
A phase I study published in January 2007 by researchers at the University of Alberta, who had tested DCA on human cancer cells grown in mice, found that DCA restored mitochondrial function, thus restoring apoptosis, allowing cancer cells to self-destruct and shrink the tumor.
These results received extensive media attention, beginning with an article in New Scientist titled “Cheap, ‘safe’ drug kills most cancers”. Subsequently, the American Cancer Society and other medical organizations have received a large volume of public interest and questions regarding DCA. Clinical trials in humans with cancer have not been conducted in the USA and are not yet final in Canada, emphasizing the need for caution in interpreting the preliminary results.
Results of phase II clinical trials
In in vitro studies, Evangelos Michelakis of University of Alberta found that in tissue samples from 49 patients, DCA caused depolarization of mitochondria in GBM tissue but not in healthy brain tissue.
Five palliative patients with primary GBM were entered into a phase II trial. Three had not responded to several chemotherapies; two were newly diagnosed. After surgical removal of tumor mass, they were treated with DCA and chemotherapy.
Of the five patients tested, one died after three months. The surviving four were followed for 15 months. Their Karnofsky scores were unchanged in two cases, and decreased by 10 points in two patients.
DCA was associated with tumor regression and had a good safety profile. DCA side effects were minimal.
Michelakis is proceeding with phase three human studies with private funding from philanthropic groups and individuals. DCA’s legal status as a discovery is public domain because it was made or discovered as far back as 1864 and has been used in the treatment of canine and human lactic acidosis, some who presented at the beginning of treatment with cancer.
Concerns about pre-trial use
Following its initial publication, The New Scientist later editorialized, “The drug may yet live up to its promise as an anti-cancer agent – clinical trials are expected to start soon. It may even spawn an entirely new class of anti-cancer drugs. For now, however, it remains experimental, never yet properly tested in a person with cancer. People who self-administer the drug are taking a very long shot and, unlikely as it may sound, could even make their health worse.”
In 2010, it was found that for human colorectal tumours grown in mice, under hypoxic conditions, DCA decreased rather than increased apoptosis, resulting in enhanced growth of the tumours. These findings suggest that at least in some cancer types DCA treatment could be detrimental to patient health, highlighting the need for further testing before it can be considered a safe and effective cancer treatment.
Planned and ongoing clinical trials
DCA is non-patentable as a compound, though a patent has been filed for its use in cancer treatment. Research by Evangelos Michelakis has received no support from the pharmaceutical industry. Concerns have been raised that without strong intellectual property protection, the financial incentive for drug development is reduced, and therefore obtaining sufficient funds to conduct clinical trials presents difficulty. However, other sources of funding exist; previous studies of DCA have been funded by government organizations such as the National Institutes of Health, the Food and Drug Administration, the Canadian Institutes of Health Researchand by private charities (e.g. the Muscular Dystrophy Association). Recognizing anticipated funding challenges, Michelakis’s lab took the unorthodox step of directly soliciting online donations to fund the research. After 6 months, his lab had raised over $800,000, enough to fund a small Clinical Phase 2 study. Michelakis and Archer have applied for a patent on the use of DCA in the treatment of cancer.
On 24 September 2007, the Department of Medicine of Alberta University reported that after the trial funding was secured, both the Alberta local ethics committee and Health Canada approved the first DCA clinical trial for cancer. This initial trial was relatively small with enrollment of up to 50 patients. The trial was completed in August 2009. In May 2010 the team published a press releasestating no conclusions could be drawn as a result of the trial. A paper describing the results was published but not linked from the press release. Only five patients had been treated with the drug during the trial.
In May 2011, online reports suggested that the Alberta group had released new data which the media “had not reported”. However, this appeared to be caused by confusion between dates (the previous update was May 2010) and cancer charities moved quickly to counter these rumours, which were subsequently covered in New Scientist magazine.
The use of this compound as an anti-cancer agent has been patented.
Reports in the lay press after the 2007 University of Alberta announcement claim that dichloroacetate “has actually been used safely in humans for decades”, DCA is generally well tolerated, even in children. Short-term, infused, bolus doses of DCA at 50 mg/kg/day have been well tolerated.
At sustained, higher doses(generally 25 mg/kg/day taken orally, or greater), there is increased risk of several reversible toxicities, especially peripheral neuropathy, neurotoxicity, and gait disturbance.
Studies have also shown that it can be carcinogenic in male B6C3F1 mice at high doses.
A clinical trial where DCA was given to patients of MELAS (a form of genetically inherited lactic acidosis) at 25 mg/kg/day was ended prematurely due to excessive peripheral nerve toxicity. Dichloroacetate can also have anxiolytic or sedative effects.
Animal studies suggest that the neuropathy and neurotoxicity during chronic dichloroacetate treatment may be partly due to depletion of thiamine, and thiamine supplementation in rats reduced these effects. However, more recent studies in humans suggest that peripheral neuropathy is a common side effect during chronic DCA treatment, even with coadministration of oral thiamine. An additional study reported that 50 mg/kg/day DCA treatment resulted in unsteady gait and lethargy in two patients, with symptoms occurring after one month for one patient and two months for the second. Gait disturbance and consciousness were recovered with cessation of DCA, however sensory nerve action potentials did not recover in one month.
It has been reported that animals and patients treated with DCA have elevated levels of delta-aminolevulinic acid (delta-ALA) in the urine. A study published in 2008 suggests that this product may be the cause of the neurotoxic side effect of DCA by blocking peripheralmyelin formation.
Long term use (three years or more) of high doses (> 77 mg/kg/day) of DCA has been shown to increase risk of liver cancer in mice.Studies of the trichloroethylene (TCE) metabolites dichloroacetic acid (DCA), trichloroacetic acid (TCA), and chloral hydrate suggest that both DCA and TCA are involved in TCE-induced liver tumorigenesis and that many DCA effects are consistent with conditions that increase the risk of liver cancer in humans. It should be noted here that the maximum recommended dose for cancer treatment is 20mg/kg/day (less than 1/3rd of the 77mg/kg/day shown to increase liver cancer risk in mice).
Doctors warned of potential problems if people attempt to try DCA outside a controlled clinical trial. “If it starts going badly, who is following you before it gets out of control? By the time you realize your liver is failing, you’re in big trouble”, said Laura Shanner, Associate Professor of Health Ethics at the University of Alberta.
- ^ a b c d Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press.ISBN 1439855110.
- ^ J.T. Baker MSDS
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- ^ Bonnet, Sébastien; Archer, Stephen L.; Allalunis-Turner, Joan; Haromy, Alois; Beaulieu, Christian; Thompson, Richard; Lee, Christopher T.; Lopaschuk, Gary D. et al. (2007). “A Mitochondria-K+ Channel Axis Is Suppressed in Cancer and Its Normalization Promotes Apoptosis and Inhibits Cancer Growth”. Cancer Cell 11 (1): 37–51.doi:10.1016/j.ccr.2006.10.020 . PMID 17222789.
- ^ a b c “DCA: Cancer Breakthrough or Urban Legend?” FromABC News, 5 February 2007. Accessed 15 February 2007.
- ^ a b “No Wonder Drug” , letter to New Scientist from Ralph Moss Lemont. Published February 3, 2007. Accessed 16 February 2007.
- ^ a b c d Michelakis, E. D.; Sutendra, G.; Dromparis, P.; Webster, L.; Haromy, A.; Niven, E.; Maguire, C.; Gammer, T. L. et al. (2010). “Metabolic Modulation of Glioblastoma with Dichloroacetate” . Sci Transl Med 2 (31): 31ra34–31ra34.doi:10.1126/scitranslmed.3000677 . PMID 20463368.
- ^ T. E. (Thomas Edward) Thorpe. A Dictionary of Applied Chemistry. Vol. 3. Page 9 of 189 at http://www.ebooksread.com/authors-eng/t-e-thomas-edward-thorpe/a-dictionary-of-applied-chemistry-volume-3-hci/page-9-a-dictionary-of-applied-chemistry-volume-3-hci.shtml
- ^ “Editorial: Gambling with your life” , New Scientist, 31 March 2007
- ^ a b Shahrzad, Siranoush; Lacombe, Kristen; Adamcic, Una; Minhas, Kanwal; Coomber, Brenda L. (November 2010). “Sodium dichloroacetate (DCA) reduces apoptosis in colorectal tumor hypoxia”. Cancer Letters 297 (1): 75–83.doi:10.1016/j.canlet.2010.04.027 . PMID 20537792.
- ^ a b “CTV.ca: Researchers launch website on new cancer research” . CTV News.
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- ^ “Small molecule offers big hope against cancer” , by Ryan Smith. From ExpressNews, a University of Alberta publication. Published January 16, 2007. Accessed 15 February 2007.
- ^ Official University of Alberta DCA Site
- ^ A Method of Treating Cancer Using Dichloroacetate , Application to the European Patent Office, 19 October 2006
- ^http://www.dca.med.ualberta.ca/Home/Updates/letter_092407.pdf , 24 September 2007
- ^ The Safety and Efficacy of DCA for the Treatment of Brain Cancer , ClinicalTrials.gov identifier: NCT00540176
- ^ Outlook 2008 , Tufts Center for the Study of Drug Development
- ^ Michelakis, ED; Sutendra, G; Dromparis, P; Webster, L; Haromy, A; Niven, E; Maguire, C; Gammer, TL et al. (2010). “Metabolic modulation of glioblastoma with dichloroacetate”.Science translational medicine 2 (31): 31ra34–31ra34.doi:10.1126/scitranslmed.3000677 . PMID 20463368.
- ^ The Cure for Cancer Has Been Found and is Purposely Being Ignored – Technorati blog (accessed 16/05/2011)
- ^ DCA Research Team publishes results of Clinical Trials – University of Alberta website
- ^ Potential cancer drug DCA tested in early trials – Cancer Research UK science blog
- ^ @CR_UK tweet – tweeted 16/05/11
- ^ Cancer drug resurfaces and threatens false optimism – New Scientist, 16 May 2011
- ^ US 8071645 , Newell, M. Karen; Newell, Evan & Villalobos-Menuey, Elizabeth, “Systems and methods for treating human inflammatory and proliferative diseases and wounds, with fatty acid metabolism inhibitors and/or glycolytic inhibitors”
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- ^ Agbenyega T, Planche T, Bedu-Addo G, Ansong D, Owusu-Ofori A, Bhattaram VA, Nagaraja NV, Shroads AL, Henderson GN, Hutson AD, Derendorf H, Krishna S, Stacpoole PW (2003). “Population kinetics, efficacy, and safety of dichloroacetate for lactic acidosis due to severe malaria in children”. J Clin Pharmacol. 43 (4): 386–396.doi:10.1177/0091270003251392 . PMID 12723459.
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- ^ Kaufmann P, Engelstad K, Wei Y et al. (2006). “Dichloroacetate causes toxic neuropathy in MELAS: a randomized, controlled clinical trial”. Neurology 66 (3): 324–330. doi:10.1212/01.wnl.0000196641.05913.27 .PMID 16476929.
- ^ Stacpoole P, Harwood H, Cameron D, Curry S, Samuelson D, Cornwell P, Sauberlich H (1990). “Chronic toxicity of dichloroacetate: possible relation to thiamine deficiency in rats”.Fundam Appl Toxicol 14 (2): 327–37. doi:10.1016/0272-0590(90)90212-3 . PMID 2318357.
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- International Chemical Safety Card 0868
- CTV.ca News Staff (16 January 2007). “Small molecule offers hope for cancer treatment” . CTV.ca Website (CTV television network). Retrieved 2007-01-31.
- DCA Research Information Website (University of Alberta)
- Wait for Clinical Trials , New Scientist, 24 February 2007
- Potential cancer drug DCA tested in early trials , by Cancer Research UK
- Interviewing Drs. Akbar and Humaira Khan about DCA
- Cancer Biology – Cramping Tumors Economist, January 18, 2007
- Official University of Alberta DCA (dichloroacetate) Website , The University of Alberta Discovery. March 15, 2007
Telephone Orders: 1-347-535-4322 (New York area)
We are VERY busy, if you get the answering machine leave your name and phone number, we will call you back.
UPDATE we now have DCA in capsules
333 mg per capsule, Click To Buy DCA
60 Day DCA Treatment Kit is now available in the DCA Store
What’s New With Dichloroacetate?
February 2012 Video added “Using a Scale to Measure DCA”
August 31, 2011 Doctor Flavin, M.D. read his letter Doctor Flavin’s letter
March 20, 2011 Read how one person beat cancer using DCA.
May 12, 2010 Latest Positive DCA Clinical Trials and More! Visit the University of Alberta (the university site is currently down, try this link to read about the doctor )
Recent Medical Research at a Canadian University has confirmed that scientists do understand the cause of cancer. The dying off of old cells to be replaced by new cells is a normal part of our cellular lifecycle and keeps us well. It seems that in cancerous cells, our body has forgotten how to tell the aged cells how to die off and be replaced by healthy new cells. This process is governed by the mitochondria and is known as “cell death” or “apoptosis”. In a cancer cell, the mitochondria has lost the ability to direct the cell to die off – the sick cell becomes “immortal”, spreading and making the person increasingly unwell. Recent Medical trials using Pure DCA have proven this compound can reactivate the mitochondria restoring the cell’s original function of “apoptosis” enabling shrinkage in tumor size and mass. Testimonials have shown reversal in illness, remission, clean health tests, increased health and vitality. Favourable results (scientifically measurable) have been accomplished within days (less than a week) of starting treatment with Pure DCA.
“Dr. Evangelos Michelakis, a professor at the U of A Department of Medicine, has shown that dichloroacetate (DCA) causes regression in several cancers, including lung, breast, and brain tumors.”
Sodium dichloroacetate offered by PureDCA.com is more than 99% pure. It is made using a sophisticated synthesis process. No organic solvents are used during the production. WE SHIP DCA WORLDWIDE.
We are working with Doctors around the world but also service individual orders for Pure DCA for those looking for an alternative cancer treatment. You do NOT need a prescription.
We ship dichloroacetate internationally, with no exceptions. We are a reliable source of sodium dichloroacetate (Pure DCA). Buy sodium dichloroacetate.
Below you can find a description of the main sections of this website.
- Buy DCA Online or by Telephone
- Pure DCA Powder is available in 3 sizes: 20 grams, 50 grams, and 100 grams
- Pure DCA in Capsules (333mg)
- Pure Powdered Thiamine (Vitamin B1)
- Pure NAC Powder (N-Acetyle L-Cysteine)
- Medicinal dosing scales also available
Pure DCA Information
The main facts about sodium dichloroacetate, pure DCA
Frequently Asked Questions
Dichloroacetate has been used in recent human trials and was found to shrink tumors. These trials were done by a university and their results have been published for anyone to read about the dichloroacetate cancer connection. The link to the universities dichloroacetate study.
- How Marijuana Fights Cancer (peterbdunn.wordpress.com)
- Health & Toxins – Re: The End of Cancer. DCA makes its world debut. (disclose.tv)