Identification
- Generic Name
- Dichloroacetic acid
- DrugBank Accession Number
- DB08809
- Background
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abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms. 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.
DCA was approved for use in Canada in 1989 (as a topical formulation for treatment of warts and for cauterization and removal of a wide variety of skin and tissue lesions), but was cancelled post market.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Dichloroacetic acid (DB08809)
- Weight
- Average: 128.942
Monoisotopic: 127.943184722 - Chemical Formula
- C2H2Cl2O2
- Synonyms
- DCA
- Dichloracetic acid
- Dichloroacetate
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism A[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 1, mitochondrial inhibitorHumans UMaleylacetoacetate isomerase Not Available Humans - 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
- Adverse Effects
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ORAL (LD50): Acute: 2820 mg/kg [Rat]; DERMAL (LD50): Acute: 510 mg/kg Rabbit
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Sodium dichloroacetate Not Available Not Available Not applicable - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bichloracetic Acid 100% Liquid 100 % / kit Topical Glenwood Inc. 1989-12-31 2010-07-16 Canada 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Alpha-halocarboxylic acids and derivatives
- Direct Parent
- Alpha-halocarboxylic acids
- Alternative Parents
- Monocarboxylic acids and derivatives / Carboxylic acids / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Alkyl chlorides
- Substituents
- Aliphatic acyclic compound / Alkyl chloride / Alkyl halide / Alpha-halocarboxylic acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- monocarboxylic acid, organochlorine compound (CHEBI:36386) / Halogenated fatty acids (LMFA01090070)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9LSH52S3LQ
- CAS number
- 79-43-6
- InChI Key
- 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
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 References
- Not Available
- External Links
- KEGG Compound
- C11149
- PubChem Compound
- 6597
- PubChem Substance
- 175427097
- ChemSpider
- 10771217
- BindingDB
- 227588
- 155021
- ChEBI
- 36386
- ChEMBL
- CHEMBL13960
- ZINC
- ZINC000003830689
- PharmGKB
- PA165947835
- PDBe Ligand
- TF4
- Wikipedia
- Dichloroacetic_acid
- PDB Entries
- 2bu8 / 2q8h
- MSDS
- Download (49.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Unknown Status Basic Science Resistance, Insulin 1 3 Active Not Recruiting Treatment Pyruvate Dehydrogenase Complex Deficiency 1 2 Completed Treatment Malignant Gliomas, Glioblastoma Multiforme 1 2 Completed Treatment Squamous Cell Carcinoma of the Head and Neck (SCCHN) 1 2 Not Yet Recruiting Treatment High Grade Glioma: Glioblastoma (GBM) 1 2 Recruiting Treatment Glioblastoma Multiforme (GBM) 1 2 Terminated Treatment Lung Cancer / Metastatic Breast Cancer 1 2 Unknown Status Treatment Mitochondrial Encephalomyopathy, Lactic Acidosis and Stroke Like Episodes (MELAS) 1 1 Completed Health Services Research Healthy Subjects (HS) 1 1 Completed Screening Healthy Subjects (HS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Topical 100 % / kit - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 13.5 °C PhysProp boiling point (°C) 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 72.3 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 22.62 m3·mol-1 Chemaxon Polarizability 9.32 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8954 CYP450 2D6 inhibitor Non-inhibitor 0.9359 CYP450 2C19 inhibitor Non-inhibitor 0.9162 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- 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 de...
- Gene Name
- PDK1
- Uniprot ID
- Q15118
- Uniprot Name
- [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial
- Molecular Weight
- 49243.765 Da
References
- Stacpoole PW: The pharmacology of dichloroacetate. Metabolism. 1989 Nov;38(11):1124-44. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein homodimerization activity
- Specific Function
- Bifunctional enzyme showing minimal glutathione-conjugating activity with ethacrynic acid and 7-chloro-4-nitrobenz-2-oxa-1,3-diazole and maleylacetoacetate isomerase activity. Has also low glutathi...
- Gene Name
- GSTZ1
- Uniprot ID
- O43708
- Uniprot Name
- Maleylacetoacetate isomerase
- Molecular Weight
- 24212.005 Da
References
- Anderson WB, Liebler DC, Board PG, Anders MW: Mass spectral characterization of dichloroacetic acid-modified human glutathione transferase zeta. Chem Res Toxicol. 2002 Nov;15(11):1387-97. [Article]
Drug created at January 06, 2011 23:41 / Updated at December 13, 2022 10:46