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Identification
- Generic Name
- Oxogluric acid
- DrugBank Accession Number
- DB08845
- Background
Oxogluric acid (α-Ketoglutarate) is not approved for any indication in the world but is an investigational drug in the United States. In the United States a phase I clinical trial is investigating whether oxogluric acid precursors found in nutritional supplements can benefit patients with the metabolic disorder propionic acidemia. Oxogluric acid is sold as a dietary supplement to athletes to improve their performance by helping to remove excess ammonia, but it is not officially approved for this indication and only experimental studies have shown a reduction in ammonia by oxogluric acid in hemodialysis patients. Physiologically, oxogluric acid acts in the Krebs cycle as an intermediate, is involved in transamination reactions during the metabolism of amino acids, forms glutamic acid by combining with ammonia, and reduces nitrogen by combining with it as well. Several experimental studies have also shown that administration of oxogluric acid helped attenuate the decreased synthesis of muscle protein that is often seen post-surgery.
- Type
- Small Molecule
- Groups
- Experimental, Investigational, Nutraceutical
- Structure
Structure for Oxogluric acid (DB08845)
- Weight
- Average: 146.0981
Monoisotopic: 146.021523302 - Chemical Formula
- C5H6O5
- Synonyms
- 2-Ketoglutaric acid
- 2-oxoglutaric acid
- 2-oxopentanedioic acid
- alpha-Ketoglutaric acid
- Ketoglutaric acid
- Oxoglurate
- α-Ketoglutarate
- External IDs
- NSC-17391
Pharmacology
- Indication
α-α-Ketoglutarate is not approved for any indication in the world but is an investigational drug in the United States. The potential indications for α-Ketoglutarate are in patients with the metabolic disorder propionic acidemia and in trauma patients with muscle loss.
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All of the physiological roles of alpha-ketoglutarate have not been determined. What is known is that alpha-keotglutarate is involved in the Krebs cycle, transamination reactions, and promotes muscle synthesis.
- Mechanism of action
The exact mechanisms of action for α-Ketoglutarate have not yet been elucidated. Some of α-Ketoglutarate’s actions include acting in the Krebs cycle as an intermediate, transamination reactions during the metabolism of amino acids, forming glutamic acid by combining with ammonia, and reducing nitrogen by combining with it as well. Concerning α-Ketoglutarate’s actions with ammonia, it is proposed that α-Ketoglutarate can help patients with propionic academia who have high levels of ammonia and low levels of glutamine/glutamate in their blood. Because endogenous glutamate/glutamine is produced from α-Ketoglutarate, propionic acidemia patients have impaired production of α-Ketoglutarate and supplementation of α-Ketoglutarate should improve the condition of these patients. Several other experimental studies have also shown that administration of α-Ketoglutarate in parenteral nutrition given to post-operative patients helped attenuate the decreased synthesis of muscle protein that is often seen after a surgery. This decreased muscle synthesis is speculated to be due to too low α-Ketoglutarate levels.
Target Actions Organism UAspartate aminotransferase Not Available Escherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CUSTODIOL Oxogluric acid (0.1461 g/L) + Calcium chloride dihydrate (0.0022 g/L) + Histidine (27.9289 g/L) + Histidine monohydrochloride monohydrate (3.7733 g/L) + Magnesium chloride hexahydrate (0.8132 g/L) + Mannitol (5.4651 g/L) + Potassium chloride (0.671 g/L) + Sodium chloride (0.8766 g/L) + Tryptophan (0.4085 g/L) Solution Extracorporeal Dr. Franz Kohler Chemie Gmbh 2020-10-02 Not applicable Italy 
CUSTODIOL Oxogluric acid (0.1461 g/L) + Calcium chloride dihydrate (0.0022 g/L) + Histidine (27.9289 g/L) + Histidine monohydrochloride monohydrate (3.7733 g/L) + Magnesium chloride hexahydrate (0.8132 g/L) + Mannitol (5.4651 g/L) + Potassium chloride (0.671 g/L) + Sodium chloride (0.8766 g/L) + Tryptophan (0.4085 g/L) Solution Extracorporeal Dr. Franz Kohler Chemie Gmbh 2020-10-02 Not applicable Italy CUSTODIOL Oxogluric acid (0.1461 g/L) + Calcium chloride dihydrate (0.0022 g/L) + Histidine (27.9289 g/L) + Histidine monohydrochloride monohydrate (3.7733 g/L) + Magnesium chloride hexahydrate (0.8132 g/L) + Mannitol (5.4651 g/L) + Potassium chloride (0.671 g/L) + Sodium chloride (0.8766 g/L) + Tryptophan (0.4085 g/L) Solution Extracorporeal Dr. Franz Kohler Chemie Gmbh 2020-10-02 Not applicable Italy CUSTODIOL Oxogluric acid (0.1461 g/L) + Calcium chloride dihydrate (0.0022 g/L) + Histidine (27.9289 g/L) + Histidine monohydrochloride monohydrate (3.7733 g/L) + Magnesium chloride hexahydrate (0.8132 g/L) + Mannitol (5.4651 g/L) + Potassium chloride (0.671 g/L) + Sodium chloride (0.8766 g/L) + Tryptophan (0.4085 g/L) Solution Extracorporeal Dr. Franz Kohler Chemie Gmbh 2020-10-02 Not applicable Italy CUSTODIOL Oxogluric acid (0.1461 g/L) + Calcium chloride dihydrate (0.0022 g/L) + Histidine (27.9289 g/L) + Histidine monohydrochloride monohydrate (3.7733 g/L) + Magnesium chloride hexahydrate (0.8132 g/L) + Mannitol (5.4651 g/L) + Potassium chloride (0.671 g/L) + Sodium chloride (0.8766 g/L) + Tryptophan (0.4085 g/L) Solution Extracorporeal Dr. Franz Kohler Chemie Gmbh 2020-10-02 Not applicable Italy
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Keto acids and derivatives
- Sub Class
- Gamma-keto acids and derivatives
- Direct Parent
- Gamma-keto acids and derivatives
- Alternative Parents
- Short-chain keto acids and derivatives / Dicarboxylic acids and derivatives / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Alpha-hydroxy ketone / Alpha-keto acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Gamma-keto acid / Hydrocarbon derivative / Ketone
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- oxo dicarboxylic acid (CHEBI:30915)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8ID597Z82X
- CAS number
- 328-50-7
- InChI Key
- KPGXRSRHYNQIFN-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
- IUPAC Name
- 2-oxopentanedioic acid
- SMILES
- OC(=O)CCC(=O)C(O)=O
References
- Synthesis Reference
Tanaka, Katsunobu; kimura, Kazu; Yamaguchi, Ken. Fermentative production of a-oxoglutaric acid. U.S. (1973), 4 pp.
- General References
- Wernerman J, Hammarqvist F, Vinnars E: Alpha-ketoglutarate and postoperative muscle catabolism. Lancet. 1990 Mar 24;335(8691):701-3. [Article]
- Allen, Loyd V., Jr. (2012). Remington : The Science and Practice of Pharmacy (22nd ed.). Pharmaceutical Press. [ISBN:978-0857110626]
- External Links
- Human Metabolome Database
- HMDB0000208
- KEGG Compound
- C00026
- ChemSpider
- 50
- BindingDB
- 50303766
- 17511
- ChEBI
- 30915
- ChEMBL
- CHEMBL1686
- ZINC
- ZINC000001532519
- PDBe Ligand
- AKG
- Wikipedia
- Alpha-Ketoglutaric_acid
- PDB Entries
- 1aib / 1bl5 / 1cw4 / 1drt / 1dry / 1ds1 / 1e5i / 1ea0 / 1gp4 / 1gp5 … show 380 more
- MSDS
- Download (47.3 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Extracorporeal Solution Extracorporeal; Intrabiliary; Intracardiac - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 114 °C (237 °F) From MSDS. water solubility 100 g/l at 20 °C (68 °F) From MSDS. - Predicted Properties
Property Value Source Water Solubility 53.1 mg/mL ALOGPS logP -0.6 ALOGPS logP -0.11 Chemaxon logS -0.44 ALOGPS pKa (Strongest Acidic) 2.66 Chemaxon pKa (Strongest Basic) -9.7 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 91.67 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 28.88 m3·mol-1 Chemaxon Polarizability 12.17 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5552 Blood Brain Barrier + 0.8548 Caco-2 permeable - 0.7596 P-glycoprotein substrate Non-substrate 0.7148 P-glycoprotein inhibitor I Non-inhibitor 0.9645 P-glycoprotein inhibitor II Non-inhibitor 0.8463 Renal organic cation transporter Non-inhibitor 0.936 CYP450 2C9 substrate Non-substrate 0.8498 CYP450 2D6 substrate Non-substrate 0.9016 CYP450 3A4 substrate Non-substrate 0.7087 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9612 CYP450 2D6 inhibitor Non-inhibitor 0.9707 CYP450 2C19 inhibitor Non-inhibitor 0.9708 CYP450 3A4 inhibitor Non-inhibitor 0.9749 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9894 Ames test Non AMES toxic 0.8752 Carcinogenicity Non-carcinogens 0.8462 Biodegradation Ready biodegradable 0.9535 Rat acute toxicity 1.3416 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9774 hERG inhibition (predictor II) Non-inhibitor 0.9541
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 130.3173595 predictedDarkChem Lite v0.1.0 [M-H]- 130.3494595 predictedDarkChem Lite v0.1.0 [M-H]- 130.3219595 predictedDarkChem Lite v0.1.0 [M-H]- 122.509 predictedDeepCCS 1.0 (2019) [M-H]- 130.3173595 predictedDarkChem Lite v0.1.0 [M-H]- 130.3494595 predictedDarkChem Lite v0.1.0 [M-H]- 130.3219595 predictedDarkChem Lite v0.1.0 [M-H]- 122.509 predictedDeepCCS 1.0 (2019) [M+H]+ 129.3162595 predictedDarkChem Lite v0.1.0 [M+H]+ 130.5767595 predictedDarkChem Lite v0.1.0 [M+H]+ 130.8546595 predictedDarkChem Lite v0.1.0 [M+H]+ 125.64657 predictedDeepCCS 1.0 (2019) [M+H]+ 129.3162595 predictedDarkChem Lite v0.1.0 [M+H]+ 130.5767595 predictedDarkChem Lite v0.1.0 [M+H]+ 130.8546595 predictedDarkChem Lite v0.1.0 [M+H]+ 125.64657 predictedDeepCCS 1.0 (2019) [M+Na]+ 130.4785595 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.3893595 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.4911595 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.30305 predictedDeepCCS 1.0 (2019) [M+Na]+ 130.4785595 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.3893595 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.4911595 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.30305 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- identical protein binding
- Gene Name
- aspC
- Uniprot ID
- P00509
- Uniprot Name
- Aspartate aminotransferase
- Molecular Weight
- 43572.965 Da
References
Drug created at February 27, 2013 22:15 / Updated at June 12, 2020 16:52