Sodium dichloroacetate

Sodium dichloroacetate is a metabolic regulator in cancer cells' mitochondria with anticancer activity. Sodium dichloroacetate inhibits PDHK, resulting in decreased lactic acid in the tumor microenvironment. Sodium dichloroacetate increases reactive oxygen species (ROS) generation and promotes cancer cell apoptosis. Sodium dichloroacetate also works as NKCC inhibitor[1].

Sodium Dichloroacetate is the sodium salt of dichloroacetic acid with potential antineoplastic activity. Dichloroacetate ion inhibits pyruvate dehydrogenase kinase, resulting in the inhibition of glycolysis and a decrease in lactate production. This agent may stimulate apoptosis in cancer cells by restoring normal mitochondrial-induced apoptotic signaling.|A derivative of ACETIC ACID that contains two CHLORINE atoms attached to its methyl group.

The Sodium dichloroacetate, with the cas register number 2156-56-1, has its IUPAC name of sodium 2,2-dichloroacetate. This is a kind of white powder, and is soluble in cold water.

The characteristics of this chemical are as below: (1)H-Bond Acceptor: 2; (2)Rotatable Bond Count: 1; (3)Exact Mass: 149.925129; (4)MonoIsotopic Mass: 149.925129; (5)Topological Polar Surface Area: 40.1; (6)Heavy Atom Count: 7; (7)Formal Charge: 0; (8)Complexity: 64.7; (9)Covalently-Bonded Unit Count: 2.

Uses of Sodium dichloroacetate: Sodium dichloroacetate could react with ethane-1,2-diamine and 4-bromo-phenol to produce dibromo N,N'-ethylenebis[2-(o-hydroxyphenyl)glycines]. The reaction condition is below: reagent: 6 N NaOH; solution:H2O, methanol; reaction time: 24 hours; reaction temp.: 85 ℃; field: 30%.

You should be cautious while dealing with this chemical. Being a kind of irritant chemical, it is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. So while using this, you should take the following instructions. Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

The following datas could be converted into the molecular structure:
(1)Canonical SMILES: C(C(=O)[O-])(Cl)Cl.[Na+]
(2)InChI: InChI=1S/C2H2Cl2O2.Na/c3-1(4)2(5)6;/h1H,(H,5,6);/q;+1/p-1?
(3)InChIKey: LUPNKHXLFSSUGS-UHFFFAOYSA-M?

Below are the toxicity information which have been tested:

CHEMICAL IDENTIFICATION

RTECS NUMBER :

AG9275000

CHEMICAL NAME :

Acetic acid, dichloro-, sodium salt

CAS REGISTRY NUMBER :

2156-56-1

LAST UPDATED :

199801

DATA ITEMS CITED :

13

MOLECULAR FORMULA :

C2-H-Cl2-O2.Na

MOLECULAR WEIGHT :

150.92

WISWESSER LINE NOTATION :

QVYGG &-NA-

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :

LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - rat

DOSE/DURATION :

5281 mg/kg

TOXIC EFFECTS :

Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :

LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - mouse

DOSE/DURATION :

4845 mg/kg

TOXIC EFFECTS :

Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :

LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :

Intraperitoneal

SPECIES OBSERVED :

Rodent - mouse

DOSE/DURATION :

>3 gm/kg

TOXIC EFFECTS :

Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - rat

DOSE/DURATION :

30425 mg/kg/12W-C

TOXIC EFFECTS :

Brain and Coverings - changes in brain weight Endocrine - changes in adrenal weight Kidney, Ureter, Bladder - changes in bladder weight

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - rat

DOSE/DURATION :

45500 mg/kg/13W-I

TOXIC EFFECTS :

Endocrine - hypoglycemia Liver - changes in liver weight Blood - changes in erythrocyte (RBC) count

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - rat

DOSE/DURATION :

2450 mg/kg/7W-C

TOXIC EFFECTS :

Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - mouse

DOSE/DURATION :

61 gm/kg/12W-C

TOXIC EFFECTS :

Peripheral Nerve and Sensation - recording from peripheral motor nerve Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Mammal - dog

DOSE/DURATION :

4550 mg/kg/13W-I

TOXIC EFFECTS :

Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - food intake (animal) Blood - changes in erythrocyte (RBC) count

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

SPECIES OBSERVED :

Rodent - mouse

DOSE/DURATION :

164 gm/kg/1Y-C

TOXIC EFFECTS :

Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

DOSE :

182 gm/kg

SEX/DURATION :

male 13 week(s) pre-mating

TOXIC EFFECTS :

Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

DOSE :

4375 mg/kg

SEX/DURATION :

male 10 week(s) pre-mating

TOXIC EFFECTS :

Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :

TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :

Oral

DOSE :

2188 mg/kg

SEX/DURATION :

male 10 week(s) pre-mating

TOXIC EFFECTS :

Reproductive - Paternal Effects - testes, epididymis, sperm duct

MUTATION DATA

TYPE OF TEST :

Mutation in microorganisms

TEST SYSTEM :

Bacteria - Salmonella typhimurium

DOSE/DURATION :

5 ug/plate

REFERENCE :

AJCNAC American Journal of Clinical Nutrition. (American Soc. for Clinical Nutrition, Inc., 9650 Rockville Pike, Bethesda, MD 20814) V.2- 1954- Volume(issue)/page/year: 33,1179,1980

Sodium dichloroacetate (DCA) is a mitochondrial pyruvate dehydrogenase kinase inhibitor, and is an orally absorbable small molecular compound for MELAS syndrome, and children with congenital lactic acidosis and other diseases that are treated in the clinic. Recent studies had found that DCA acts as a potential vasoprotective agent by inhibiting PDK2 and reducing coronary endarterium proliferation. Further, DCA promotes brain regeneration after cerebral ischemia, which indicates that DCA might play an important role in VD.