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Details

Stereochemistry ACHIRAL
Molecular Formula C5H6O5
Molecular Weight 146.0981
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXOGLURIC ACID

SMILES

OC(=O)CCC(=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

Molecular Formula C5H6O5
Molecular Weight 146.0981
Charge 0
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

Alpha-ketoglutarate (AKG), an endogenous intermediary metabolite in the Krebs cycle, is a molecule involved in multiple metabolic and cellular pathways. As an intermediate of the tricarboxylic acid cycle, AKG is essential for the oxidation of fatty acids, amino acids, and glucose. Extracellular AKG is a significant source of energy for cells of the gastrointestinal tract. As a precursor for the synthesis of glutamate and glutamine in multiple tissues (including liver, skeletal muscle, heart, brain, and white adipose tissue), AKG bridges carbohydrate and nitrogen metabolism for both conservation of amino acids and ammonia detoxification. Additionally, emerging evidence shows that AKG is a regulator of gene expression and cell signaling pathways (including the mammalian target of rapamycin and AMPactivated protein kinase). Thus, AKG is an attractive dietary supplement in animal and human nutrition to improve cellular energy status, immunity, and health.AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in the skeletal muscles and can be used in clinical applications. In addition to these health benefits, a recent study has shown that AKG can extend the lifespan of adult Caenorhabditis elegans by inhibiting ATP synthase and TOR. Orally, AKG 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, AKG 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.

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
[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
In vitro and in vivo evaluation of various carbonyl compounds against cyanide toxicity with particular reference to alpha-ketoglutaric acid.
2008
Patents

Sample Use Guides

1 capsule daily
Route of Administration: Oral
It was investigated the efficacy of several carbonyl compounds and their metabolites or nutrients with alpha-ketoglutaric acid (A-KG), citric acid, succinic acid, maleic acid, malic acid, fumaric and oxaloacetic acid, glucose, sucrose, fructose, mannitol, sorbitol, dihydroxyacetone, and glyoxal (5 or 10 mM; -10 min) against toxicity of potassium cyanide (KCN; 10 mM) in rat thymocytes in vitro. Six hours after KCN, cell viability measured by MTT assay and crystal violet dye exclusion revealed maximum cytoprotection by A-KG, followed by oxaloacetic acid. A-KG also resolved the leakage of intracellular lactate dehydrogenase, loss in nuclear integrity (propidium iodide staining), and altered mitochondrial membrane potential (rhodamine 123 assay) as a result of cyanide toxicity. Protection Index (ratio of LD(50) of KCN in protected and unprotected animals; PI) of all the compounds (oral; 1.0 g/kg; -10 min) determined in male mice, revealed that maximum protection was afforded by A-KG (7.6 PI), followed by oxaloacetic acid (6.4 PI). Comparative evaluation of various salts of A-KG alone or with STS (intraperitoneal; 1.0 g/kg; -15 min) showed that maximum protection was conferred by disodium anhydrous salt of A-KG, which also significantly prevented the inhibition of brain cytochrome oxidase caused by 0.75 LD(50) KCN.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:42:22 UTC 2023
Edited
by admin
on Wed Jul 05 22:42:22 UTC 2023
Record UNII
8ID597Z82X
Record Status Validated (UNII)
Record Version
  • Download
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
A-KETOGLUTARIC ACID
Common Name English
.ALPHA.-KETOGLUTARIC ACID [MI]
Common Name English
GLUTARIC ACID, 2-OXO-
Common Name English
Oxogluric acid [WHO-DD]
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 Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
LOINC 27271-6
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
LOINC 29507-1
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
LOINC 13678-8
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
LOINC 21040-1
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
DSLD 1052 (Number of products:129)
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
LOINC 69802-7
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
LOINC 69803-5
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
LOINC 1817-6
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
Code System Code Type Description
SMS_ID
100000128818
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
NSC
17391
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
INN
4207
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID5033179
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
DAILYMED
8ID597Z82X
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
CONCEPT Dietary Supplement
CHEBI
30915
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
DRUG BANK
DB08845
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
PUBCHEM
51
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-330-3
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
CAS
328-50-7
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
WIKIPEDIA
ALPHA-KETOGLUTARIC ACID
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
MERCK INDEX
M6620
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY Merck Index
RXCUI
17511
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C83527
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
FDA UNII
8ID597Z82X
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
EVMPD
SUB36364
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
CHEBI
16810
Created by admin on Wed Jul 05 22:42:22 UTC 2023 , Edited by admin on Wed Jul 05 22:42:22 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY