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Details

Stereochemistry ACHIRAL
Molecular Formula C11H11NO2
Molecular Weight 189.2105
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-INDOLEPROPIONIC ACID

SMILES

OC(=O)CCC1=CNC2=C1C=CC=C2

InChI

InChIKey=GOLXRNDWAUTYKT-UHFFFAOYSA-N
InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)

HIDE SMILES / InChI

Description

3-Indolepropionic acid (IN-OX1; Indole-3-propionic acid; OX-1; Oxigon; SHP 22; SHP-622; VP-20629), an endogenous substance produced by bacteria in the intestine, is a deamination product of Tryptophan (T947200) that protects the hippocampus (studied in gerbils) from ischemic damage and oxidative stress. It’s ability to protect the neurons in this way is attributed to its potent antioxidative effects. 3-Indolepropionic acid is also hypothesized to have protective effects on the thyroid gland. 3-Indolepropionic acid is being studied for therapeutic use in Alzheimer's disease. 3-Indolepropionic acid (IPA) completely protected primary neurons and neuroblastoma cells against oxidative damage and death caused by exposure to Abeta, by inhibition of superoxide dismutase, or by treatment with hydrogen peroxide. In kinetic competition experiments using free radical-trapping agents, the capacity of IPA to scavenge hydroxyl radicals exceeded that of melatonin, an indoleamine considered to be the most potent naturally occurring scavenger of free radicals. In contrast with other antioxidants, IPA was not converted to reactive intermediates with pro-oxidant activity. In 2011, Intellect redirected the focus of the OX1 program from Alzheimer's disease to FA (Friedreich's Ataxia). Research suggests that the symptoms associated with FA are the result of oxidative stress caused by the abnormal accumulation of iron. OX1's ability to neutralize ROS could be an effective agent to reduce oxidative stress in FA, thereby eliminating the symptoms of FA and increasing both quality of life and longevity in affected individuals.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Friedreich's Ataxia treatment: subjects will receive multiple doses of 3-Indolepropionic acid (VP 20629) (300 mg, 600 mg, or 900 mg total daily dose) or placebo. VP20629 or placebo will be administered every 8 hours for 7 days with a single morning dose on Day 8.
Route of Administration: Oral
In Vitro Use Guide
In the primary rat hippocampal cultures evaluated by bodipy green fluorescence, 1uM Abeta treatment resulted in almost complete reduction of cell fluorescence as compared with untreated cells. In these experiments, similar concentrations (1 uM) of 3-Indolepropionic acid (IPA) or melatonin added to Abeta-containing media were sufficient to provide full protection from the neurotoxic effects of Abeta, as evidenced by levels of fluorescence comparable to control primary neurons.