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Details

Stereochemistry ACHIRAL
Molecular Formula C3H3BrO3
Molecular Weight 166.958
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMOPYRUVATE

SMILES

OC(=O)C(=O)CBr

InChI

InChIKey=PRRZDZJYSJLDBS-UHFFFAOYSA-N
InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)

HIDE SMILES / InChI

Molecular Formula C3H3BrO3
Molecular Weight 166.958
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Bromopyruvate is an halogenated analogue of pyruvic acid known as an alkylating agent reacting with thiol groups of many proteins. Bromopyruvate exerts anticancer action. It is based on the impairment of energy metabolism of tumor cells by inhibiting enzymes in the glycolysis pathway (hexokinase II, glyceraldehyde 3-phosphate dehydrogenase, phosphoglycerate kinase) and the oxidative phosphorylation (succinate dehydrogenase). Bromopyruvate induces endoplasmic reticulum stress, inhibits global protein synthesis further contributing to cancer cell death. Treatment with bromopyruvate has been administered in several cancer type models both in vitro and in vivo, either alone or in combination with other anticancer therapeutic approaches. These studies clearly demonstrate bromopyruvate broad action against multiple cancer types. This compound has also antifungal and antiparasitic activity.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.67 µM [IC50]

PubMed

Substance Class Chemical
Record UNII
63JMV04GRK
Record Status Validated (UNII)
Record Version