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Identification
NameDichloroacetic Acid
Accession NumberDB08809
TypeSmall Molecule
GroupsExperimental
Description

Dichloroacetic acid, often abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms. The salts and esters of dichloroacetic acid are called dichloroacetates. Salts of DCA are used as drugs since they inhibit the enzyme pyruvate dehydrogenase kinase. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. A phase 1 study in 5 patients concluded that DCA was safe, but wasn’t designed to establish effectiveness.

Structure
Thumb
Synonyms
DCA
dichloracetic acid
dichloroacetate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bichloracetic Acid 100%liquid100 %topicalGlenwood Inc.1989-12-312010-07-16Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII9LSH52S3LQ
CAS number79-43-6
WeightAverage: 128.942
Monoisotopic: 127.943184722
Chemical FormulaC2H2Cl2O2
InChI KeyInChIKey=JXTHNDFMNIQAHM-UHFFFAOYSA-N
InChI
InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)
IUPAC Name
2,2-dichloroacetic acid
SMILES
OC(=O)C(Cl)Cl
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAlpha-halocarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityORAL (LD50): Acute: 2820 mg/kg [Rat]; DERMAL (LD50): Acute: 510 mg/kg [Rabbit]
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9891
Blood Brain Barrier+0.9763
Caco-2 permeable+0.6135
P-glycoprotein substrateNon-substrate0.9118
P-glycoprotein inhibitor INon-inhibitor0.9924
P-glycoprotein inhibitor IINon-inhibitor0.9909
Renal organic cation transporterNon-inhibitor0.9443
CYP450 2C9 substrateNon-substrate0.7947
CYP450 2D6 substrateNon-substrate0.9283
CYP450 3A4 substrateNon-substrate0.7764
CYP450 1A2 substrateNon-inhibitor0.7252
CYP450 2C9 inhibitorNon-inhibitor0.8954
CYP450 2D6 inhibitorNon-inhibitor0.9359
CYP450 2C19 inhibitorNon-inhibitor0.9162
CYP450 3A4 inhibitorNon-inhibitor0.9544
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9909
Ames testAMES toxic0.5797
CarcinogenicityCarcinogens 0.7098
BiodegradationReady biodegradable0.5292
Rat acute toxicity1.9655 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9854
hERG inhibition (predictor II)Non-inhibitor0.9796
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Liquidtopical100 %
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point13.5 °CPhysProp
boiling point194 °CPhysProp
water solubility1E+006 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.92HANSCH,C ET AL. (1995)
pKa1.26MARUTHAMUTHU,P & HUIE,RE (1995)
Predicted Properties
PropertyValueSource
Water Solubility72.3 mg/mLALOGPS
logP0.99ALOGPS
logP1.06ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.62 m3·mol-1ChemAxon
Polarizability9.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-5cc2c87638085fad9afcView in MoNA
1D NMR1H NMR SpectrumNot Available
References
Synthesis Reference

Joanne D. Burger, William L. Howard, “Method for preparing pentachloroacetone and dichloroacetic acid from isopropyl ethers.” U.S. Patent US3996272, issued August, 1968.

US3996272
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Pyruvate dehydrogenase (acetyl-transferring) kinase activity
Specific Function:
Kinase that plays a key role in regulation of glucose and fatty acid metabolism and homeostasis via phosphorylation of the pyruvate dehydrogenase subunits PDHA1 and PDHA2. This inhibits pyruvate dehydrogenase activity, and thereby regulates metabolite flux through the tricarboxylic acid cycle, down-regulates aerobic respiration and inhibits the formation of acetyl-coenzyme A from pyruvate. Play...
Gene Name:
PDK1
Uniprot ID:
Q15118
Molecular Weight:
49243.765 Da
References
  1. Stacpoole PW: The pharmacology of dichloroacetate. Metabolism. 1989 Nov;38(11):1124-44. [PubMed:2554095 ]
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Drug created on January 06, 2011 16:41 / Updated on August 17, 2016 12:24