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Dichloroacetic acid
IUPAC name Dichloroacetic acid
Other names Dichloroethanoic acid
Molecular formula CHCl2COOH
Identifiers
CAS number [79-43-6]
PubChem 6597
MeSH Dichloroacetate
RTECS number AG6125000
SMILES ClC(Cl)C(=O)O
Properties
Molar mass 128. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component Medical Subject Headings ( MeSH) is a huge Controlled vocabulary (or metadata system for the purpose of indexing journal articles and books Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 9 g/mol
Appearance colorless liquid
Density 1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 57 g/ml, liquid
Melting point

13. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C
Boiling point

194 °C
Solubility in water miscible
Acidity (pKa) 1. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 25[1]
Hazards
MSDS MSDS (jtbaker)
NFPA 704
1
3
0
 
R-phrases R35, R50
S-phrases (S1/2), S26, S45, S61
Related compounds
Related chloroacetic acids Chloroacetic acid
Trichloroacetic acid
Related compounds Acetic acid
Difluoroacetic acid
Dibromoacetic acid
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Dichloroacetic acid, often abbreviated DCA, is a chemical compound, an acid, and an analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. In Organic chemistry, the chloroacetic acids (systematic name chloroethanoic acids) are three related chlorocarbon Carboxylic acids Chloroacetic acid is the Chemical compound with the formula ClCH2CO2H Trichloroacetic acid (also known as trichloroethanoic acid) is an analogue of Acetic acid in which the three Hydrogen atoms of the Methyl Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are For other uses see Analog (disambiguation. In Chemistry, analogs or analogues are compounds in which one or Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 History See also Atomic theory, Atomism The concept that matter is composed of discrete units and cannot be divided into arbitrarily tiny In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and The salts and esters of dichloroacetic acid are called dichloroacetates. Salt is a Dietary mineral composed primarily of Sodium chloride that is essential for Animal life but toxic to most land plants Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least The salts are under investigation as a possible treatment for cancer. Cancer (medical term Malignant Neoplasm) is a class of Diseases in which a group of cells display uncontrolled

Contents

Chemistry and occurrence

The chemistry of dichloroacetic acid is typical for halogenated organic acids. Abundance Owing to their high Reactivity, the halogens are found in the environment only in compounds or as Ions Halide ions and oxoanions An organic acid is an Organic compound with Acidic properties It is a member of the chloroacetic acids family. In Organic chemistry, the chloroacetic acids (systematic name chloroethanoic acids) are three related chlorocarbon Carboxylic acids The dichloroacetate ion is produced when dissolved in water. As an acid with a pKa of 1. 48,[2] pure dichloroacetic acid is very corrosive and extremely destructive to tissues of the mucous membranes and upper respiratory tract. [3]

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. Chlorination is the process of adding the element Chlorine to Water as a method of Water purification to make it fit for human consumption as Metabolism is the set of Chemical reactions that occur in living Organisms in order to maintain Life. Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and [4] It is typically prepared by the reduction of trichloroacetic acid. Trichloroacetic acid (also known as trichloroethanoic acid) is an analogue of Acetic acid in which the three Hydrogen atoms of the Methyl

Therapeutic use

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. Sodium (ˈsoʊdiəm is an element which has the symbol Na( Latin natrium, from Arabic natrun) atomic number 11 atomic mass 22 Potassium (pəˈtæsiəm is a Chemical element. It has the symbol K (kalium from qalīy Atomic number 19 and Atomic mass 39

Lactic acidosis

The dichloroacetate ion stimulates the activity of the enzyme pyruvate dehydrogenase by inhibiting the enzyme pyruvate dehydrogenase kinase. An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins Pyruvate dehydrogenase (E1 is the first component Enzyme of Pyruvate dehydrogenase complex (PDC Pyruvate dehydrogenase kinase (also pyruvate dehydrogenase complex kinase, PDC kinase, or PDK;) is a Kinase Enzyme which acts to [5] Thus, it decreases lactate production by shifting the metabolism of pyruvate from glycolysis towards oxidation in the mitochondria. Lactic acid ( IUPAC Systematic name: 2-hydroxypropanoic acid) also known as milk acid, is a Chemical compound that plays a role Pyruvic acid (CH3COCO2H is an alpha-keto acid. The Carboxylate Anion of pyruvic acid is known as pyruvate. See also Gluconeogenesis, which carries out a process wherein glucose is synthesized rather than catabolized Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state In Cell biology, a mitochondrion (plural mitochondria) is a membrane-enclosed Organelle found in most eukaryotic cells. This property has led to trials of DCA for the treatment of lactic acidosis in humans. Lactic acidosis is a condition caused by the buildup of Lactic acid in the body [6][7][8][9]

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 randomized controlled trial (RCT is a type of scientific Experiment most commonly used in testing the Efficacy or Effectiveness of Healthcare Lactic acidosis is a condition caused by the buildup of Lactic acid in the body [7] 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. Mitochondrial Myopathy, Encephalopathy, Lactic acidosis, stroke-like episodes, abbreviated to MELAS is one of the family of Mitochondrial In Cell biology, a mitochondrion (plural mitochondria) is a membrane-enclosed Organelle found in most eukaryotic cells. Peripheral neuropathy is the term for damage to Nerves of the Peripheral nervous system, which may be caused either by diseases of the Nerve or from the [8] 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 hemodynamics or survival. Hemodynamics, meaning literally "blood movement" is the study of Blood flow or the circulation [9]

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 use glycolysis rather than oxidation for energy (the Warburg effect), as a result of hypoxia that exists in tumors and damaged mitochondria. See also Gluconeogenesis, which carries out a process wherein glucose is synthesized rather than catabolized Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state The phrase "Warburg effect" is used for two unrelated observations in Biochemistry, one in Plant physiology and the other in Oncology, both due Chronic Hypoxia is a pathological condition in which the body as a whole ( generalized hypoxia) or region of the body ( tissue hypoxia) is deprived of adequate See also Cancer A tumor or tumour is the name for a swelling or lesion formed by an abnormal growth of cells (termed neoplastic [10] The body often kills damaged cells by apoptosis, a mechanism of self-destruction that involves mitochondria, but this mechanism fails in cancer cells. Cancer (medical term Malignant Neoplasm) is a class of Diseases in which a group of cells display uncontrolled According to the Warburg hypothesis of cancer growth, cancer is caused by the metabolic changes in mitochondria, although it is now known that cancer is caused by mutations in the genome of the cells. Warburg's hypothesis was postulated by the Nobel laureate Otto Heinrich Warburg in 1924

A study published in January 2007 by researchers at the University of Alberta,[11] testing DCA on in vitro cancer cell lines and a rat model, found that DCA restored mitochondrial function, thus restoring apoptosis, killing cancer cells in vitro, and shrinking the tumors in the rats. The University of Alberta (U of A is a public research University located in Edmonton, Alberta, Canada. In vitro ( Latin: within the glass refers to the technique of performing a given experiment in a controlled environment outside of a living Organism [12]

These results received extensive media attention, beginning with an article in New Scientist titled "Cheap, ‘safe’ drug kills most cancers". New Scientist is a weekly International science magazine and website covering recent developments in science and technology for a general English -speaking [13] Subsequently, the American Cancer Society and other medical organizations have received a large volume of public interest and questions regarding DCA. The American Cancer Society ( ACS) is the "nationwide community-based voluntary health organization dedicated to [14] Reports have since pointed out that although the study results are promising, no formal clinical trials in humans with cancer have yet been conducted, emphasizing the need for caution in interpreting the preliminary results,[14][15] though some doctors are treating patients with DCA "off-label",[16][17] and under a cloud of controversy. In health care clinical trials are conducted to allow safety and Efficacy data to be collected for new drugs or devices [18] Medicor Cancer Centres, a private clinic in Toronto, run by the husband-and-wife team of Drs. Toronto (təˈrɒntoʊ colloquially pronounced or) is the largest city in Canada and is the provincial capital of Ontario Humaira and Akbar Khan, is since March 2007[19] using DCA off-label for the treatment of several cancers and said on their web site that some patients "are showing varied positive responses to DCA including tumour shrinkage, reduction in tumour markers, symptom control, and improvement in lab tests". [17] However, they have not published their results nor reported it at medical conferences. Dr. Terry Polevoy, of Kitchener, Ontario, called on the College of Physicians and Surgeons of Ontario to take away the Khans' licences for offering a compound that hasn't been proven to shrink tumours in humans. "They are not oncologists. They should not be making these decisions. I think they should be disciplined for using this stuff. That, to me, is unethical, to use something that has never been proved to do anything. " But the College said that it was not their role to say which therapies a doctor can use. [20]

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. "[21]

More than 90% of drugs entering phase I trials are found unacceptable. [22] The FDA approves 8-11% of drugs entering Phase I testing. [23][24] DCA has been used historically to treat patients with lactic acidosis, and therefore could arguably enter phase 2 trials in patients with cancer. [25]

DCA is non-patentable as a compound, though a patent has been filed for its use in cancer treatment. A patent is a set of Exclusive rights granted by a State to an inventor or his assignee for a fixed period of time in exchange for a disclosure of an [26] Research by Dr. Evangelos Michelakis has received no support from the pharmaceutical industry. Concerns have been raised that without strong intellectual property protection, the financial incentive for pharmaceutical industry interest is reduced, and therefore clinical trials of DCA may not be funded. [14][13][15][27] 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 Research and by private charities (e. "NIH" redirects here For other meanings of NIH see NIH (disambiguation. Canadian Institutes of Health Research (CIHR is the major federal agency responsible for funding health research in Canada. g. the Muscular Dystrophy Association). The Muscular Dystrophy Association ( MDA) is an organization founded in 1950 which combats Muscular dystrophy and diseases of the Nervous system Recognizing anticipated funding challenges, Dr Michelakis's lab took the unorthodox step of directly soliciting online donations to fund the research. [28] After 6 months, his lab had raised over $800,000, enough to fund a small Clinical Phase 2 study. Dr. Michelakis and Dr. Archer have applied for a patent on the use of DCA in the treatment of cancer. [29][30]

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 in Cancer. Events 622 - Prophet Muhammad completes his hegira from Mecca to Medina. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Health Canada ( French: Santé Canada) is the department of the government of Canada with responsibility for national Public health [31] This initial trial will be relatively small (enrollment- up to 50 patients in the following 18 months). The patients will originate from the Edmonton area and be available for scheduled assessments for the duration of the trial.

Side effects

Reports in the lay press after the 2007 University of Alberta announcement claim that dichloroacetate "has actually been used safely in humans for decades",[32] but the limited scholarly literature suggests side effects of pain, numbness and gait disturbances in some patients. The University of Alberta (U of A is a public research University located in Edmonton, Alberta, Canada. Human gait is the way Locomotion is achieved using human limbs For this article different gaits do not require changes in the geometry of motion but rather [32] 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. Mitochondrial Myopathy, Encephalopathy, Lactic acidosis, stroke-like episodes, abbreviated to MELAS is one of the family of Mitochondrial Lactic acidosis is a condition caused by the buildup of Lactic acid in the body [33] Dichloroacetate can also have anxiolytic or sedative effects. An anxiolytic is a drug prescribed for the treatment of Symptoms of Anxiety. Sedation is a Medical procedure involving the administration of Sedative drugs generally to facilitate a medical procedure with Local anaesthesia. [4]

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. Neuropathy is a medical term usually short for Peripheral neuropathy. Neurotoxicity occurs when the exposure to natural or artificial toxic substances which are called Neurotoxins alters the normal activity of the Nervous system in For the similarly spelled pyrimidine see Thymine Thiamin or thiamine, also known as Vitamin B1 [34] 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. [35][36] 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. Sensory nerves are nerves that receive sensory stimuli such as how something feels and if it is painful In Neurophysiology, the action potential is a self-regenerating Wave of Electrochemical activity that allows Nerve cells to carry a signal [37]

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. The Chemical compound trichloroethylene is a chlorinated Hydrocarbon commonly used as an industrial Solvent. Trichloroacetic acid (also known as trichloroethanoic acid) is an analogue of Acetic acid in which the three Hydrogen atoms of the Methyl Chloral hydrate is a Sedative and Hypnotic drug as well as a Chemical reagent and precursor Carcinogenesis (meaning literally the creation of Cancer) is the process by which normal cells are transformed into cancer cells Hepatocellular carcinoma (HCC also called hepatoma) is a primary malignancy (cancer of the Liver. [38]

Self-medication

Doctors warned of potential problems if people attempt to try DCA outside a controlled clinical trial. In health care clinical trials are conducted to allow safety and Efficacy data to be collected for new drugs or devices "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. [39]

Two websites founded by Jim Tassano, an operator at a pest-control company in Sonora, California, claim to promote information about DCA and its potential benefits for pets and humans. TheDCASite. com aims “to be the meeting place, for the world, where all important information on DCA is gathered and shared". The second website, BuyDCA. com, manufactured and sold DCA to the public until the FDA ordered the site to cease production and sales of the compound. [40] According to Phil Walsky, an FDA special agent who investigated the two websites, it is illegal to sell DCA online for human or animal consumption in the U. S. because it has not been approved for such uses. [41]

References

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  3. ^ MSDS (jtbaker)
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  11. ^ depmed.ualberta.ca
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  13. ^ a b Cheap, ‘safe’ drug kills most cancers. New Scientist (2007-01-17). Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 38 BC - Octavian marries Livia Drusilla. 1287 - King Alfonso III of Aragon invades Minorca Retrieved on 2007-01-17. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 38 BC - Octavian marries Livia Drusilla. 1287 - King Alfonso III of Aragon invades Minorca
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  20. ^ Doctors prescribe DCA to cancer patients. Retrieved on 2007-10-08. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 314 - Roman Emperor Licinius is defeated by his colleague Constantine I at the Battle of Cibalae, and loses
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  22. ^ Society for Clinical Trials Board of Directors. The Society for Clinical Trials opposes US legislation to permit marketing of unproven medical therapies for seriously ill patients. Events 307 - After divorcing his wife Minervina, Constantine marries Fausta, the daughter of the retired Roman Emperor Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Clin Trials 2006;3:154. [Free Full Text]
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  32. ^ a b "Long-used drug shows new promise for cancer", The Globe and Mail, 2007-01-17. Events 565 - Eutychius is deposed as Patriarch of Constantinople by John Scholasticus. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 202 BCE - The Battle of Zama results in the defeat of Carthage and Hannibal. Year 2006 ( MMVI) was a Common year starting on Sunday of the Gregorian calendar. Events 622 - Prophet Muhammad completes his hegira from Mecca to Medina. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. The Globe and Mail is a Canadian English language nationally distributed Newspaper, based in Toronto and printed in six cities Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 38 BC - Octavian marries Livia Drusilla. 1287 - King Alfonso III of Aragon invades Minorca Retrieved on 2007-01-17. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 38 BC - Octavian marries Livia Drusilla. 1287 - King Alfonso III of Aragon invades Minorca  
  33. ^ Kaufmann P, Engelstad K, Wei Y et al. (2006). "Dichloroacetate causes toxic neuropathy in MELAS: a randomized, controlled clinical trial". Neurology 66 (3): 324–30. doi:10.1212/01.wnl.0000196641.05913.27. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 16476929.  
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  39. ^ Andrea Sands. "Experts caution against patients compiling own data on unapproved cancer drug", Edmonton Journal, March 18, 2007. Events 37 - The Roman Senate annuls Tiberius ' will and proclaims Caligula emperor Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century.  
  40. ^ Illegal ‘cancer drug’ website shut down, Linda Geddes. New Scientist (27 July 2007). New Scientist is a weekly International science magazine and website covering recent developments in science and technology for a general English -speaking Events 1214 - Battle of Bouvines: In France, Philip II of France defeats John of England. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century.
  41. ^ Cancer therapy: When all else fails, Linda Geddes. New Scientist (28 March 2007). New Scientist is a weekly International science magazine and website covering recent developments in science and technology for a general English -speaking Events 37 - Roman Emperor Caligula accepts the titles of the Principate, entitled to him by the Senate. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century.

External links

The University of Alberta (U of A is a public research University located in Edmonton, Alberta, Canada. Events 303 - Galerius, Roman Emperor, publishes his edict that begins the persecution of Christians in his portion of the Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 350 - Generallus Magnentius deposes Roman Emperor Constans and proclaims himself Emperor Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century.
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