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Identification
- Generic Name
- Dehydroascorbic acid
- DrugBank Accession Number
- DB08830
- Background
Dehydroascorbic acid is made from the oxidation of ascorbic acid. This reaction is reversible, but dehydroascorbic acid can instead undergo irreversible hydrolysis to 2,3-diketogulonic acid. Dehydroascorbic acid as well as ascorbic acid are both termed Vitamin C, but the latter is the main form found in humans. In the body, both dehydroascorbic acid and ascorbic acid have similar biological activity as antivirals but dehydroascorbic acid also has neuroprotective effects. Currently dehydroascorbic acid is an experimental drug with no known approved indications.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Dehydroascorbic acid (DB08830)
- Weight
- Average: 174.1082
Monoisotopic: 174.016437924 - Chemical Formula
- C6H6O6
- Synonyms
- dehydro-L-ascorbic acid
- DHAA
- L-dehydroascorbate
- L-dehydroascorbic acid
- L-threo-2,3-hexodiulosonic acid, γ-lactone
- L-threo-hexo-2,3-diulosono-1,4-lactone
- Oxidized ascorbic acid
- Oxidized vitamin C
Pharmacology
- Indication
There is no approved indication for dehydroascorbic acid, but it has potential therapeutic use in patients with certain viruses and ischemic stroke.
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Dehydroascorbic acid has similar biological activity as ascorbic acid. Both compounds have been shown to have antiviral effects against herpes simplex virus type 1, influenza virus type A and poliovirus type 1 with dehydroascorbic acid having the stronger effect. In addition, unlike ascorbic acid, dehydroascorbic acid can cross the blood brain barrier and is then converted to ascorbic acid to enable retention in the brain. This is important because one study has found that after an ischemic stroke, dehydroascorbic acid has neuroprotective effects by reducing infarct volume, neurological deficits, and mortality.
- Mechanism of action
Even though dehydroascorbic acid and ascorbic acid have similar effects, their mechanism of action seems to be different. The exact mechanism of action is still being investigated, but some have been elucidated. Concerning dehydroascorbic acid's antiviral effect against herpes simplex virus type 1, it is suggested that dehydroascorbic acid acts after replication of viral DNA and prevents the assembly of progeny virus particles.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmphetamine The serum concentration of Amphetamine can be decreased when it is combined with Dehydroascorbic acid. Benzphetamine The serum concentration of Benzphetamine can be decreased when it is combined with Dehydroascorbic acid. Bleomycin The therapeutic efficacy of Bleomycin can be decreased when used in combination with Dehydroascorbic acid. Bortezomib The therapeutic efficacy of Bortezomib can be decreased when used in combination with Dehydroascorbic acid. Chlorpropamide Dehydroascorbic acid may decrease the excretion rate of Chlorpropamide which could result in a higher serum level. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactones
- Sub Class
- Gamma butyrolactones
- Direct Parent
- Gamma butyrolactones
- Alternative Parents
- Furanones / Tetrahydrofurans / Secondary alcohols / Cyclic ketones / Carboxylic acid esters / 1,2-diols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides show 1 more
- Substituents
- 1,2-diol / 3-furanone / Alcohol / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Gamma butyrolactone / Hydrocarbon derivative show 9 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- dehydroascorbic acid (CHEBI:27956)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Y2Z3ZTP9UM
- CAS number
- 490-83-5
- InChI Key
- SBJKKFFYIZUCET-JLAZNSOCSA-N
- InChI
- InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
- IUPAC Name
- (5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
- SMILES
- [H][C@](O)(CO)[C@@]1([H])OC(=O)C(=O)C1=O
References
- General References
- Agus DB, Gambhir SS, Pardridge WM, Spielholz C, Baselga J, Vera JC, Golde DW: Vitamin C crosses the blood-brain barrier in the oxidized form through the glucose transporters. J Clin Invest. 1997 Dec 1;100(11):2842-8. [Article]
- Huang J, Agus DB, Winfree CJ, Kiss S, Mack WJ, McTaggart RA, Choudhri TF, Kim LJ, Mocco J, Pinsky DJ, Fox WD, Israel RJ, Boyd TA, Golde DW, Connolly ES Jr: Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11720-4. [Article]
- Furuya A, Uozaki M, Yamasaki H, Arakawa T, Arita M, Koyama AH: Antiviral effects of ascorbic and dehydroascorbic acids in vitro. Int J Mol Med. 2008 Oct;22(4):541-5. [Article]
- External Links
- KEGG Compound
- C05422
- PubChem Compound
- 440667
- PubChem Substance
- 175427110
- ChemSpider
- 389547
- ChEBI
- 27956
- ZINC
- ZINC000001532648
- PDBe Ligand
- UU3
- Wikipedia
- Dehydroascorbic_acid
- PDB Entries
- 5mye
- MSDS
- Download (46.8 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) Decomposes at 225°C (437°F) From MSDS. water solubility Soluble in water at 60°C From The Merck Index. pKa 3.90 From The Merck Index. - Predicted Properties
Property Value Source Water Solubility 190.0 mg/mL ALOGPS logP -1.2 ALOGPS logP -0.67 Chemaxon logS 0.04 ALOGPS pKa (Strongest Acidic) 7.8 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 100.9 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 33.55 m3·mol-1 Chemaxon Polarizability 14.02 Å3 Chemaxon Number of Rings 1 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 + 0.7263 Blood Brain Barrier + 0.8746 Caco-2 permeable - 0.7901 P-glycoprotein substrate Non-substrate 0.7062 P-glycoprotein inhibitor I Non-inhibitor 0.8824 P-glycoprotein inhibitor II Non-inhibitor 0.9492 Renal organic cation transporter Non-inhibitor 0.9146 CYP450 2C9 substrate Non-substrate 0.8574 CYP450 2D6 substrate Non-substrate 0.8789 CYP450 3A4 substrate Non-substrate 0.7245 CYP450 1A2 substrate Non-inhibitor 0.9302 CYP450 2C9 inhibitor Non-inhibitor 0.9737 CYP450 2D6 inhibitor Non-inhibitor 0.9608 CYP450 2C19 inhibitor Non-inhibitor 0.9683 CYP450 3A4 inhibitor Non-inhibitor 0.9769 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9906 Ames test Non AMES toxic 0.9225 Carcinogenicity Non-carcinogens 0.9203 Biodegradation Ready biodegradable 0.9583 Rat acute toxicity 1.0981 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9766 hERG inhibition (predictor II) Non-inhibitor 0.956
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.44014 predictedDeepCCS 1.0 (2019) [M-H]- 140.44014 predictedDeepCCS 1.0 (2019) [M+H]+ 142.54759 predictedDeepCCS 1.0 (2019) [M+H]+ 142.54759 predictedDeepCCS 1.0 (2019) [M+Na]+ 148.46013 predictedDeepCCS 1.0 (2019) [M+Na]+ 148.46013 predictedDeepCCS 1.0 (2019)
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Facilitative glucose transporter, which is responsible for constitutive or basal glucose uptake (PubMed:10227690, PubMed:10954735, PubMed:18245775, PubMed:19449892, PubMed:25982116, PubMed:27078104, PubMed:32860739). Has a very broad substrate specificity; can transport a wide range of aldoses including both pentoses and hexoses (PubMed:18245775, PubMed:19449892). Most important energy carrier of the brain: present at the blood-brain barrier and assures the energy-independent, facilitative transport of glucose into the brain (PubMed:10227690). In association with BSG and NXNL1, promotes retinal cone survival by increasing glucose uptake into photoreceptors (By similarity). Required for mesendoderm differentiation (By similarity)
- Specific Function
- D-glucose transmembrane transporter activity
- Gene Name
- SLC2A1
- Uniprot ID
- P11166
- Uniprot Name
- Solute carrier family 2, facilitated glucose transporter member 1
- Molecular Weight
- 54083.325 Da
References
- Korcok J, Dixon SJ, Lo TC, Wilson JX: Differential effects of glucose on dehydroascorbic acid transport and intracellular ascorbate accumulation in astrocytes and skeletal myocytes. Brain Res. 2003 Dec 12;993(1-2):201-7. [Article]
- Vera JC, Rivas CI, Fischbarg J, Golde DW: Mammalian facilitative hexose transporters mediate the transport of dehydroascorbic acid. Nature. 1993 Jul 1;364(6432):79-82. [Article]
- Agus DB, Gambhir SS, Pardridge WM, Spielholz C, Baselga J, Vera JC, Golde DW: Vitamin C crosses the blood-brain barrier in the oxidized form through the glucose transporters. J Clin Invest. 1997 Dec 1;100(11):2842-8. [Article]
Drug created at February 16, 2013 00:15 / Updated at June 12, 2020 16:52