基本情報
- 標準SMILES
O=C([O-])C(Cl)Cl- InChIKey
JXTHNDFMNIQAHM-UHFFFAOYSA-M- 分子式
- C2HCl2O2-
- 平均分子量
- 127.93 g/mol
- 単同位体質量
- 126.93590821
概要
Dichloroacetate is a monocarboxylic acid anion that is the conjugate base of dichloroacetic acid. It has a role as a geroprotector. It is functionally related to an acetate. It is a conjugate base of a dichloroacetic acid.
名称と識別子
- 優先名称
- Dichloroacetate anion
- IUPAC
- 2,2-dichloroacetate
- 現地名
- ジクロロアセタート
- 英語名
- Dichloroacetate
- 分子式
- C2HCl2O2
- 分子量
- 0
名称と別名
名称をさらに表示
データベース識別子
- CAS
13425-80-4- PubChem CID
- 25975
- DTXSID
DTXSID40158610- ChEBI
CHEBI:28240- Nikkaji
- J54.198B
物性
構造計算による物性
- XLogP
- 1.8
- 極性表面積
- 40.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 0
- 重原子数
- 6
- 形式電荷
- -1
- 複雑度
- 55.1
安全と法規制
毒性情報
Health Effects
Multiple independent studies demonstrate that DCA has the ability to alter normal carbohydrate metabolism. Dichloroacetic acid treatment results in a significant reduction in plasma levels of glucose, pyruvate, and lactate. Another consistent finding in DCA ingestion studies is a dose-related increase in liver size, generally accompanied (or caused) by an increase in glycogen deposition in the liver. There is an extensive and consistent data base demonstrating the reproductive toxicity of DCA in males and females. Neurologic symptoms and morphologic changes in the nervous system have been reported in humans, dogs, and rats. (L2086)
Toxicity Summary
The dichloroacetate ion stimulates the activity of the enzyme pyruvate dehydrogenase by inhibiting the enzyme pyruvate dehydrogenase kinase. Thus, it decreases lactate production by shifting the metabolism of pyruvate from fermentation towards oxidation in the mitochondria. (Wikipedia)
化学と産業
薬理情報
Metabolism/Metabolites
Dichloroacetic acid is metabolized in the liver by oxidative dechlorination to yield glyoxylate, which can enter intermediary metabolism and either be oxidized to oxalate and excreted, converted to carbon dioxide, and/or incorporated into amino acids or other cellular molecules. (L2086)
用途と製造
Uses
Dichloroacetic acid has shown promise as a potentially new class of anti-cancer medication, but has yet to complete clinical trials. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. As of October 2014, dichloroacetic acid was undergoing phase III clinical trials for cancer treatment (L2084) (Wikipedia). Dichloroacetic acid has undergone clinical trials for the treatment of lactic acidosis in humans, but the trials found no clinical benefit (Wikipedia). In 2014 Thomas E. Mallouk and colleagues published a new technique for the production of graphene by intercalation of graphite with non-oxidizing Brønsted acids including dichloroacetic acid, raising the prospect that dichloroacetic acid might be used in industrial graphene production in the future (L2085).
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補足説明
定義ChEBI: A monocarboxylic acid anion that is the conjugate base of dichloroacetic acid.
関連反応
関連ノート
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