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Details

Stereochemistry ACHIRAL
Molecular Formula C5H5O5.Na
Molecular Weight 168.0802
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOSODIUM OXOGLURATE

SMILES

C(CC(=O)[O-])C(=O)C(=O)O.[Na+]

InChI

InChIKey=MOTOGHHLNTXPTI-UHFFFAOYSA-M
InChI=1S/C5H6O5.Na/c6-3(5(9)10)1-2-4(7)8;/h1-2H2,(H,7,8)(H,9,10);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C5H5O5
Molecular Weight 145.0904
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://www.uofmhealth.org/health-library/hn-4451004 | https://www.ncbi.nlm.nih.gov/pubmed/27326424 | https://www.ncbi.nlm.nih.gov/pubmed/26122777 | https://www.ncbi.nlm.nih.gov/pubmed/26759695 | https://www.ncbi.nlm.nih.gov/pubmed/10453328

α-Ketoglutaric acid (AKG) is a key intermediate in the tricarboxylic acid (TCA) cycle or Krebs cycle. It also plays an important role in preventing nitrogen overload by combining with nitrogen released within the cell. It is important for the proper metabolism of all essential amino acids and the transfer of cellular energy. In combination with L-glutamate, AKG can reduce levels of ammonia formed in the brain, muscles and kidneys, as well as help balance the body’s nitrogen chemistry and prevent nitrogen excess in body tissues and fluids. Individuals with high protein intake or gastrointestinal microbiota imbalance may benefit from supplemental AKG to help balance ammonia levels and protect tissues. AKG inhibits ATP synthase subunit β and is dependent on target of rapamycin (TOR) downstream. Inhibition by AKG leads to reduced ATP content, decreased oxygen consumption. Administration of AKG has been shown to be beneficial for proper development and function of the skeletal system during growth of young organisms, as well as in adulthood. In the form of a dietary supplement it also contributes to inhibition of osteoporosis in women. Moreover, it promotes the growth of muscle mass and accelerates wound healing. AKG has a significant impact on the morphology of the gastrointestinal tract in healthy animals and animals with damaged gastrointestinal tract mucosa. It is also a promising substance for the treatment of patients with short bowel syndrome, as it stimulates beneficial changes in intestinal morphology. In addition, was shown, that α-Ketoglutarate can scavenge hydrogen peroxide generated by ascorbate and epigallocatechin gallate in cell culture media.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Primary
ORNITHINE ALPHA-KETOGLUTARATE

Approved Use

Ornithine alpha-ketoglutarate (OKG) administration improves nutritional status in chronically malnourished (e.g., elderly) and acutely malnourished patients (especially burn and trauma patients).
Primary
ALPHA-KETOGLUTARATE

Approved Use

Orally, alpha-ketoglutarate is used for kidney disease, gastrointestinal disorders, bacterial overgrowth, intestinal toxemia, liver dysfunction, and chronic candidiasis. It is also used for improving peak athletic performance, improving amino acid metabolism in hemodialysis patients, and cataracts. Intravenously, alpha-ketoglutarate is used for preventing ischemic injury during heart surgery, improving renal blood flow after heart surgery, and preventing muscle protein depletion after surgery or trauma.
PubMed

PubMed

TitleDatePubMed
Effect of ornithine alpha ketoglutarate (OAKG) on the response of brain metabolism to hypoxia in the dog.
1978 May-Jun
[A controlled trial of ornithine alpha-ketoglutarate in neuro-traumatology].
1986 Oct
The use of alpha-ketoglutarate salts in clinical nutrition and metabolic care.
1999 Jan
Nutritional and clinical efficacy of ornithine alpha-ketoglutarate in severe burn patients.
1999 Oct
Effect of alpha-ketoglutarate and oxaloacetate on brain mitochondrial DNA damage and seizures induced by kainic acid in mice.
2003 Jul 20
Ornithine alpha-ketoglutarate as a potent precursor of arginine and nitric oxide: a new job for an old friend.
2004 Oct
In vitro and in vivo evaluation of various carbonyl compounds against cyanide toxicity with particular reference to alpha-ketoglutaric acid.
2008
The absorption, tissue distribution and excretion of enteraly administered alpha-ketoglutarate in rats.
2008 Apr
The Physiological Basis and Nutritional Function of Alpha-ketoglutarate.
2015
The biological role of a-ketoglutaric acid in physiological processes and its therapeutic potential.
2016 Jan-Mar
Alpha-Ketoglutarate as a Molecule with Pleiotropic Activity: Well-Known and Novel Possibilities of Therapeutic Use.
2017 Feb
Patents

Sample Use Guides

For the healing of burn wounds: 30 grams of ornithine Alpha-ketoglutarate daily. Alpha-ketoglutarate (300 mg) 1 capsule daily. Alpha-ketoglutarate ORAL: For improving amino acid metabolism in hemodialysis patients, 1.187 grams are typically used three times daily. For improving athletic performance 0.2 grams/kg/day of a specific alpha-ketoglutarate supplement (Evonik Rexim SAS, France) has been used. Alpha-ketoglutarate INTRAVENOUS: For cardiac surgery, a dose of 28 grams of alpha-ketoglutarate has been added to blood cardioplegia. For preventing muscle protein depletion after surgery or trauma, 280 mg/kg of body weight is added to parenteral nutrition.
Route of Administration: Other
In vitro exposure of kainic acid (0.25, 0.5 or 1.0 mM) to brain homogenate inflicted damage to mtDNA in a concentration-dependent manner. The damage of mtDNA induced by 1.0 mM kainic acid was attenuated by the co-treatment with alpha-ketoglutarate (2.5 or 5.0 mM)
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:00:26 UTC 2021
Edited
by admin
on Sat Jun 26 08:00:26 UTC 2021
Record UNII
8GFV60F71R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MONOSODIUM OXOGLURATE
Common Name English
MONOSODIUM 2-OXOGLUTARATE
Systematic Name English
PENTANEDIOIC ACID, 2-OXO-, MONOSODIUM SALT
Systematic Name English
SODIUM HYDROGEN .ALPHA.-KETOGLUTARATE
Common Name English
GLUTARIC ACID, 2-OXO-, MONOSODIUM SALT
Systematic Name English
ALPHA-KETO-GLUTARIC ACID, SODIUM SALT
Common Name English
MONOSODIUM .ALPHA.-KETOGLUTARATE
Common Name English
PENTANEDIOIC ACID, 2-OXO-, SODIUM SALT (1:1)
Systematic Name English
.ALPHA.-KETOGLUTARIC ACID MONOSODIUM SALT
Common Name English
Code System Code Type Description
FDA UNII
8GFV60F71R
Created by admin on Sat Jun 26 08:00:26 UTC 2021 , Edited by admin on Sat Jun 26 08:00:26 UTC 2021
PRIMARY
PUBCHEM
23670750
Created by admin on Sat Jun 26 08:00:26 UTC 2021 , Edited by admin on Sat Jun 26 08:00:26 UTC 2021
PRIMARY
ECHA (EC/EINECS)
244-836-6
Created by admin on Sat Jun 26 08:00:26 UTC 2021 , Edited by admin on Sat Jun 26 08:00:26 UTC 2021
PRIMARY
CAS
17091-15-5
Created by admin on Sat Jun 26 08:00:26 UTC 2021 , Edited by admin on Sat Jun 26 08:00:26 UTC 2021
NON-SPECIFIC STOICHIOMETRY
CAS
22202-68-2
Created by admin on Sat Jun 26 08:00:26 UTC 2021 , Edited by admin on Sat Jun 26 08:00:26 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE