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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abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms.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
SynonymLanguageCode
DCANot AvailableNot Available
dichloroacetateNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number79-43-6
WeightAverage: 128.942
Monoisotopic: 127.943184722
Chemical FormulaC2H2Cl2O2
InChI KeyJXTHNDFMNIQAHM-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsEnolates; Carboxylic Acids; Organochlorides; Alkyl Chlorides
Substituentsorganochloride; organohalogen; alkyl halide; alkyl chloride
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9891
Blood Brain Barrier + 0.9763
Caco-2 permeable + 0.6135
P-glycoprotein substrate Non-substrate 0.9118
P-glycoprotein inhibitor I Non-inhibitor 0.9924
P-glycoprotein inhibitor II Non-inhibitor 0.9909
Renal organic cation transporter Non-inhibitor 0.9443
CYP450 2C9 substrate Non-substrate 0.7947
CYP450 2D6 substrate Non-substrate 0.9283
CYP450 3A4 substrate Non-substrate 0.7764
CYP450 1A2 substrate Non-inhibitor 0.7252
CYP450 2C9 substrate Non-inhibitor 0.8954
CYP450 2D6 substrate Non-inhibitor 0.9359
CYP450 2C19 substrate Non-inhibitor 0.9162
CYP450 3A4 substrate Non-inhibitor 0.9544
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9909
Ames test AMES toxic 0.5797
Carcinogenicity Carcinogens 0.7098
Biodegradation Ready biodegradable 0.5292
Rat acute toxicity 1.9655 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9854
hERG inhibition (predictor II) Non-inhibitor 0.9796
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
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 solubility7.23e+01 g/lALOGPS
logP0.99ALOGPS
logP1.06ChemAxon
logS-0.25ALOGPS
pKa (strongest acidic)2.3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count1ChemAxon
refractivity22.62ChemAxon
polarizability9.32ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot 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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC11149
ChEBI36386
ChEMBL
PharmGKBPA165947835
WikipediaDichloroacetic_acid
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(49.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. [Pyruvate dehydrogenase [lipoamide]] kinase isozyme 1, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 1, mitochondrial Q15118 Details

References:

  1. Stacpoole PW: The pharmacology of dichloroacetate. Metabolism. 1989 Nov;38(11):1124-44. Pubmed

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Drug created on January 06, 2011 16:41 / Updated on September 16, 2013 18:11