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Identification
Name Dichloroacetic Acid
Accession Number DB08809
Type small molecule
Groups experimental
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abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms.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
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Display: 2D Structure | 3D Structure
Synonyms
DCA
dichloroacetate
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories Not Available
CAS number 79-43-6
Weight Average: 128.942
Monoisotopic: 127.943184722
Chemical Formula C2H2Cl2O2
InChI Key InChIKey=JXTHNDFMNIQAHM-UHFFFAOYSA-N
InChI
InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)
Plain Text
IUPAC Name
2,2-dichloroacetic acid
SMILES
OC(=O)C(Cl)Cl
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Not Available
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity ORAL (LD50): Acute: 2820 mg/kg [Rat]; DERMAL (LD50): Acute: 510 mg/kg [Rabbit]
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point 13.5 °C PhysProp
boiling point 194 °C PhysProp
water solubility 1E+006 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 0.92 HANSCH,C ET AL. (1995)
pKa 1.26 MARUTHAMUTHU,P & HUIE,RE (1995)
Predicted Properties
Property Value Source
water solubility 7.23e+01 g/l ALOGPS
logP 0.99 ALOGPS
logP 1.06 ChemAxon
logS -0.25 ALOGPS
pKa (strongest acidic) 2.3 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 37.3 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 22.62 ChemAxon
polarizability 9.32 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C11149 Link_out
ChEBI 36386 Link_out
ChEMBL 36386 Link_out
PharmGKB PA165947835 Link_out
Wikipedia http://en.wikipedia.org/wiki/Dichloroacetic_acid Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (49.1 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

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

Pharmacological action: yes
Actions: inhibitor

Inhibits the mitochondrial pyruvate dehydrogenase complex by phosphorylation of the E1 alpha subunit, thus contributing to the regulation of glucose metabolism

Organism class: human
UniProt ID: Q15118 Link_out
Gene: PDK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Stacpoole PW: The pharmacology of dichloroacetate. Metabolism. 1989 Nov;38(11):1124-44. Pubmed
Comments
Drug created on January 06, 2011 16:41 / Updated on February 08, 2013 16:27