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Details

Stereochemistry ACHIRAL
Molecular Formula C5H6O5
Molecular Weight 146.0983
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXOGLURIC ACID

SMILES

C(CC(=O)O)C(=O)C(=O)O

InChI

InChIKey=KPGXRSRHYNQIFN-UHFFFAOYSA-N
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

HIDE SMILES / InChI

Description
Curator's Comment:: 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
Palliative
Palliative
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
[1 (+) ornithine alpha ketoglutarate in hepatic encephalopathy].
1970 Jun 20
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
Artefacts in cell culture: α-Ketoglutarate can scavenge hydrogen peroxide generated by ascorbate and epigallocatechin gallate in cell culture media.
2011 Mar 4
The metabolite α-ketoglutarate extends lifespan by inhibiting ATP synthase and TOR.
2014 Jun 19
The Physiological Basis and Nutritional Function of Alpha-ketoglutarate.
2015
Alpha-Ketoglutarate as a Molecule with Pleiotropic Activity: Well-Known and Novel Possibilities of Therapeutic Use.
2017 Feb
Patents

Sample Use Guides

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)
Name Type Language
OXOGLURIC ACID
MART.   WHO-DD  
Common Name English
.ALPHA.-KETOGLUTARIC ACID
MI  
Preferred Name English
2-OXO-1,5-PENTANEDIOIC ACID
Systematic Name English
ALPHA KETOGLUTARATE
Common Name English
OXOGLURIC ACID [WHO-DD]
Common Name English
A-KETOGLUTARIC ACID
Common Name English
.ALPHA.-KETOGLUTARIC ACID [MI]
Common Name English
GLUTARIC ACID, 2-OXO-
Common Name English
ALFA-KETOGLUTARIC ACID
Common Name English
2-OXOPENTANEDIOIC ACID [FHFI]
Common Name English
A-KETOGLUTARICUM ACIDUM
HPUS  
Common Name English
2-OXOGLUTARIC ACID
Systematic Name English
KETOGLUTARIC ACID [INCI]
Common Name English
OXOGLURATE [INN]
Common Name English
2-OXOPENTANEDIOIC ACID
FHFI  
Systematic Name English
OXOGLURATE
INN  
INN  
Official Name English
ALPHA-KETOGLUTARATE
Common Name English
ALPHA-KETOGLUTARIC ACID
Common Name English
A-KETOGLUTARICUM ACIDUM [HPUS]
Common Name English
KETOGLUTARIC ACID
INCI  
INCI  
Official Name English
NSC-17391
Code English
PENTANEDIOIC ACID, 2-OXO-
Common Name English
.ALPHA.-KETOGLUTARATE
Common Name English
OXOGLURIC ACID [MART.]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION 2-OXOPENTANEDIOIC ACID
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
LOINC 27271-6
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LOINC 29507-1
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
LOINC 13678-8
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
LOINC 21040-1
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
DSLD 1052 (Number of products:129)
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
LOINC 69802-7
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
LOINC 69803-5
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
LOINC 1817-6
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
Code System Code Type Description
INN
4207
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
EPA CompTox
328-50-7
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
CONCEPT Dietary Supplement
DRUG BANK
DB08845
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
PUBCHEM
51
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PRIMARY
ECHA (EC/EINECS)
206-330-3
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
CAS
328-50-7
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
WIKIPEDIA
ALPHA-KETOGLUTARIC ACID
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
MERCK INDEX
M6620
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY Merck Index
RXCUI
17511
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C83527
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
FDA UNII
8ID597Z82X
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY
EVMPD
SUB36364
Created by admin on Sat Jun 26 09:31:22 UTC 2021 , Edited by admin on Sat Jun 26 09:31:22 UTC 2021
PRIMARY