3D Mol Similar

Sodium dichloroacetate

: Iupac Name：sodium 2,2-dichloroacetate; CAS No.: 2156-56-1; Molecular Weight：150.92391; Modify Date.: 2022-11-29 09:10; Introduction: 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. View more+

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1. Names and Identifiers

: 1.1 Name; Sodium dichloroacetate; 1.2 Synonyms; Acetic acid, 2,2-dichloro-, sodium salt (1:1) ACETIC ACID,DICHLORO-,SODIUM SALT Cpc 211 dichloroacetate de sodium dichloroacetate sodium salt dichloroacetate,sodiumsalt dichloroacetic acid sodium salt dichloro-aceticacisodiumsalt Dichloroctan sodny [Czech] dichloroctansodny EINECS 218-461-3 erlcyiuanna MFCD00070489 NATRIUMDICHLORACETAT SDA Sodium 2,2-dichloroacetate Sodium dichloroacetate [USAN] sodium dichlroacetate sodium salt of dichloroacetate Sodiumdichloracetate; View all

1.3 CAS No.: 2156-56-1

1.4 CID: 517326

1.5 EINECS(EC#): 218-461-3

1.6 Molecular Formula: C2HCl2NaO2 (isomer)

1.7 Inchi: InChI=1S/C2H2Cl2O2.Na/c3-1(4)2(5)6;/h1H,(H,5,6);/q;+1/p-1

1.8 InChIkey: LUPNKHXLFSSUGS-UHFFFAOYSA-M

1.9 Canonical Smiles: C(C(=O)[O-])(Cl)Cl.[Na+]

1.10 Isomers Smiles: C(C(=O)[O-])(Cl)Cl.[Na+]

2. Properties

2.1 Density: Relative density (water = 1): 1.56

2.1 Melting point: 198℃ (dec.)

2.1 Boiling point: 194°Cat760mmHg

2.1 Flash Point: 194°Cat760mmHg

2.2 Precise Quality: 149.92500

2.2 PSA: 40.13000

2.2 logP: -0.46000

2.2 VaporDensity: Relative vapour density (air = 1): 4.4

2.3 Appearance: White Powder

2.4 Storage: Hygroscopic. Ambient temperatures.

2.5 Chemical Properties: white powder

2.6 Color/Form: Powder

2.7 Water Solubility: soluble in cold water

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 Methods of Manufacturing: A solution of Cl2CHCO2H (135 μL, 1.64 mmol) in H2O (2 mL) was treated with 1.00 M NaOH(1.60 mL, 1.60 mmol) and stirred at room temperature for 2 hours. Volatiles were then removedunder vacuum and the yellowish residue was suspended in acetone. The suspension was filtered andthe resulting colorless solid was washed with acetone and dried under vacuum. Yield: 227 mg, 96percent.

3.2 Usage: 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.

4. Safety and Handling

4.1 Symbol: GHS07, GHS08

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Class: 8

4.1 Hazard Declaration: H315-H319-H335-H351

4.1 RIDADR: 2811

4.1 Caution Statement: P261-P281-P305 + P351 + P338

4.1 WGK Germany: 2

4.1 RTECS: AG9275000

4.1 Sensitive: Moisture Sensitive

4.2 Specification

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:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	> 3gm/kg (3000mg/kg)	?	Journal of Agricultural and Food Chemistry. Vol. 10, Pg. 370, 1962.
mouse	LD50	oral	4845mg/kg (4845mg/kg)	?	Journal of Pharmacology and Experimental Therapeutics. Vol. 222, Pg. 501, 1982. ?
rat	LD50	oral	5281mg/kg (5281mg/kg)	?	Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 78, 1941.

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4.3 Toxicity

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

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in D2O

1H NMR : 90 MHz in D2O

IR : KBr disc

IR : liquid film

7. Other Information

7.0 Usage: Sodium dichloroacetate finds medicinal application in removing warts and other skin growths. It is used as an antidote for lactic acidosis and in the treatment of stroke. It is studied as potential drugs, since it inhibits the enzyme pyruvate dehydrogenase kinase.

7.1 Target: Value

7.2 PDK4 (Cell-free assay): 80 μM

7.3 PDK2 (Cell-free assay): 183 μM

7.4 Uses: 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.

7.5 Chemical Properties: white powder

7.6 Uses: Treatment of neurologic injury (pyruvate dehydrogenase activator).

7.7 Uses: Sodium dichloroacetate is an inhibitor of mitochondrial pyruvate dehydrogenase kinase.

7.8 Brand name: Ceresine (Cypros).

7.9 General Description: Sodium dichloroacetate is a mitochondrial pyruvate dehydrogenase kinase (PDK) inhibitor that exhibits potent anti-leukemic activity.

7.10 Storage Conditions: A solution of Cl2CHCO2H (135 μL, 1.64 mmol) in H2O (2 mL) was treated with 1.00 M NaOH(1.60 mL, 1.60 mmol) and stirred at room temperature for 2 hours. Volatiles were then removedunder vacuum and the yellowish residue was suspended in acetone. The suspension was filtered andthe resulting colorless solid was washed with acetone and dried under vacuum. Yield: 227 mg, 96percent.

7.11 Storage features: Separated from metals, combustible substances, reducing agents, strong oxidants, strong bases and food and feedstuffs. Well closed. Ventilation along the floor.

7.12 Mesh Entry Terms: Acid, Bichloroacetic

7.13 Use Classification: Human drugs -> Rare disease (orphan)

8. Computational chemical data

Molecular Weight: 150.92391g/mol
Molecular Formula: C₂HCl₂NaO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 149.9251289
Monoisotopic Mass: 149.9251289
Complexity: 64.7
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 40.1
Heavy Atom Count: 7
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADcQBAMCAGAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgIAAAAAAAOAgMAACAAAAAAIAACQCAAAAAAAAAAAAAAAAQBAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9. Question & Answer

What is Sodium dichloroacetate and how is it used? Sep 21 2024
Sodium dichloroacetate, also known as Sodium dichloroacetate in English, is a white solid powder at room temperature and pressure. It has a certain alkalinity and strong hygroscopicity, good solubili..
What is Sodium dichloroacetate? Aug 29 2020
Sodium Dichloroacetate is the sodium salt of dichloroacetic acid with potential antineoplastic activity. Dichloroacetate ion inhibits pyruvate dehydrogenase kinase, resulting in the inhibition of glyc..
Can Sodium Dichloroacetate be a Potential Treatment for Cancer and Vascular Dementia? Dec 30 2019
Sodium Dichloroacetate (DCA) is a promising compound with potential antineoplastic activity. By inhibiting pyruvate dehydrogenase kinase, DCA inhibits glycolysis and reduces lactate production, potent..

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Sodium Dichloroacetate CAS No 2156-56-1