Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H6O9P.3Na |
| Molecular Weight | 322.0495 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].[Na+].[H][C@@]1(OC(=O)C(OP([O-])([O-])=O)=C1[O-])[C@@H](O)CO
InChI
InChIKey=YRWWOAFMPXPHEJ-OFBPEYICSA-K
InChI=1S/C6H9O9P.3Na/c7-1-2(8)4-3(9)5(6(10)14-4)15-16(11,12)13;;;/h2,4,7-9H,1H2,(H2,11,12,13);;;/q;3*+1/p-3/t2-,4+;;;/m0.../s1
Ascorbic acid (vitamin C) is a water-soluble vitamin. It occurs as a white or slightly yellow crystal or powder with a slight acidic taste. Ascorbic acid is an electron donor, and this property accounts for all its known functions. As an electron donor, ascorbic acid is a potent water-soluble antioxidant in humans. Ascorbic acid acts as an antioxidant under physiologic conditions exhibiting a cross over role as a pro-oxidant in pathological conditions. Oxidized ascorbic acid (dehydroascorbic acid (DHA) directly inhibits IkappaBalpha kinase beta (IKKbeta) and IKKalpha enzymatic activity in vitro, whereas ascorbic acid did not have this effect. These findings define a function for vitamin C in signal transduction other than as an antioxidant and mechanistically illuminate how vitamin C down-modulates NF-kappaB signaling. Vitamin C is recommended for the prevention and treatment of scurvy. Its parenteral administration is desirable for patients with an acute deficiency or for those whose absorption of orally ingested ascorbic acid (vitamin c) is uncertain. Symptoms of mild deficiency may include faulty bone and tooth development, gingivitis, bleeding gums, and loosened teeth. Febrile states, chronic illness, and infection (pneumonia, whooping cough, tuberculosis, diphtheria, sinusitis, rheumatic fever, etc.) increase the need for ascorbic acid (vitamin c). Hemovascular disorders, burns, delayed fracture and wound healing are indications for an increase in the daily intake.
CNS Activity
Curator's Comment: Ascorbic acid readily crosses the blood-brain barrier. Ascorbate (vitamin C) is a vital antioxidant molecule in the brain. Neurodegenerative diseases typically involve high levels of oxidative stress and thus ascorbate has been posited to have potential therapeutic roles against ischemic stroke, Alzheimer's disease, Parkinson's disease, and Huntington's disease.
Originator
Curator's Comment: In 1928, Albert Szent-Györgyi isolated a substance from adrenal glands that he called 'hexuronic acid'. Four years later, Charles Glen King isolated vitamin C in his laboratory and concluded that it was the same as 'hexuronic acid'. Norman Haworth deduced the chemical structure of vitamin C in 1933.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1991 |
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Target ID: CHEMBL3476 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Vitamin C Approved UseVitamin C is recommended for the prevention and treatment of scurvy. Its parenteral administration is desirable for patients with an acute deficiency or for those whose absorption of orally ingested ascorbic acid (vitamin c) is uncertain.
Symptoms of mild deficiency may include faulty bone and tooth development, gingivitis, bleeding gums, and loosened teeth. Febrile states, chronic illness, and infection (pneumonia, whooping cough, tuberculosis, diphtheria, sinusitis, rheumatic fever, etc.) increase the need for ascorbic acid (vitamin c) .
Hemovascular disorders, burns, delayed fracture and wound healing are indications for an increase in the daily intake |
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| Preventing | Vitamin C Approved UseVitamin C is recommended for the prevention and treatment of scurvy. Its parenteral administration is desirable for patients with an acute deficiency or for those whose absorption of orally ingested ascorbic acid (vitamin c) is uncertain.
Symptoms of mild deficiency may include faulty bone and tooth development, gingivitis, bleeding gums, and loosened teeth. Febrile states, chronic illness, and infection (pneumonia, whooping cough, tuberculosis, diphtheria, sinusitis, rheumatic fever, etc.) increase the need for ascorbic acid (vitamin c) .
Hemovascular disorders, burns, delayed fracture and wound healing are indications for an increase in the daily intake |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
33 mM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23670640/ |
50 g/m² 1 times / day multiple, intravenous dose: 50 g/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ASCORBIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
124 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23670640/ |
50 g/m² 1 times / day multiple, intravenous dose: 50 g/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ASCORBIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23670640/ |
50 g/m² 1 times / day multiple, intravenous dose: 50 g/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ASCORBIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
15 mg/kg 2 times / day multiple, oral Studied dose Dose: 15 mg/kg, 2 times / day Route: oral Route: multiple Dose: 15 mg/kg, 2 times / day Sources: Page: p.541 |
unhealthy, ADULT n = 42 Health Status: unhealthy Condition: Charcot-Marie-Tooth disease Age Group: ADULT Sex: M+F Population Size: 42 Sources: Page: p.541 |
|
1.5 g/kg 3 times / week multiple, intravenous Dose: 1.5 g/kg, 3 times / week Route: intravenous Route: multiple Dose: 1.5 g/kg, 3 times / week Sources: Page: p.414 |
unhealthy, ADULT n = 15 Health Status: unhealthy Condition: Non-small cell lung cancer Age Group: ADULT Sex: M+F Food Status: FASTED Population Size: 15 Sources: Page: p.414 |
Other AEs: Diarrhea... |
110 g/m2 1 times / day multiple, intravenous Dose: 110 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 110 g/m2, 1 times / day Sources: Page: p.143 |
unhealthy, ADULT n = 3 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: Page: p.143 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Diarrhea | grade 3, 6.7% | 1.5 g/kg 3 times / week multiple, intravenous Dose: 1.5 g/kg, 3 times / week Route: intravenous Route: multiple Dose: 1.5 g/kg, 3 times / week Sources: Page: p.414 |
unhealthy, ADULT n = 15 Health Status: unhealthy Condition: Non-small cell lung cancer Age Group: ADULT Sex: M+F Food Status: FASTED Population Size: 15 Sources: Page: p.414 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vanadium and ascorbate effects on 3-hydroxy-3-methylglutaryl coenzyme A reductase, cholesterol and tissue minerals in guinea pigs fed low-chromium diets. | 1991-1992 |
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| Role of heme oxygenase-1 in the regulation of manganese superoxide dismutase gene expression in oxidatively-challenged astroglia. | 2000 Oct |
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| The reappraisal of nephrocalcin--its role in the inhibition of calcium oxalate crystal growth and interaction with divalent metal ions. | 2001 Apr |
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| Effect of methoxychlor on antioxidant system of goat epididymal sperm in vitro. | 2001 Dec |
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| Antiviral effects of pyrrolidine dithiocarbamate on human rhinoviruses. | 2002 Jun |
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| Ascorbic-acid transporter Slc23a1 is essential for vitamin C transport into the brain and for perinatal survival. | 2002 May |
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| Flavonoid inhibition of sodium-dependent vitamin C transporter 1 (SVCT1) and glucose transporter isoform 2 (GLUT2), intestinal transporters for vitamin C and Glucose. | 2002 May 3 |
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| Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
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| L-ascorbic acid stimulates expression of smooth muscle-specific markers in smooth muscle cells both in vitro and in vivo. | 2003 Dec |
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| Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme. | 2003 Jun |
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| Bisphenol A induces reactive oxygen species generation in the liver of male rats. | 2003 Jun 30 |
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| Apoptosis of lymphocytes induced by chromium(VI/V) is through ROS-mediated activation of Src-family kinases and caspase-3. | 2003 Nov 1 |
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| Effects of supplementation with vitamins A, C, and E, selenium, and zinc on immune function in a murine sensitization model. | 2003 Nov-Dec |
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| Toluene diisocyanate exposure induces laryngo-tracheal eosinophilia, which can be ameliorated by supplementation with antioxidant vitamins in guinea pigs. | 2003 Oct |
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| Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization. | 2003 Oct 15 |
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| Lutein interacts with ascorbic acid more frequently than with alpha-tocopherol to alter biomarkers of oxidative stress in female zucker obese rats. | 2003 Sep |
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| Micronutrient deficiencies as predisposing factors for hypertension in lacto-vegetarian Indian adults. | 2004 Jun |
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| Platelet activating factor receptor binding plays a critical role in jet fuel-induced immune suppression. | 2004 Mar 15 |
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| Copper ions and hypochlorite are mainly responsible for oxidative inactivation of paraoxon-hydrolyzing activity in human high density lipoprotein. | 2004 Mar 7 |
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| Effects of vitamin C and aspirin in ischemic stroke-related lipid peroxidation: results of the AVASAS (Aspirin Versus Ascorbic acid plus Aspirin in Stroke) Study. | 2005 |
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| Studies on the protective role of vitamin C and E against polychlorinated biphenyl (Aroclor 1254)--induced oxidative damage in Leydig cells. | 2005 Nov |
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| Ascorbic acid deficiency stimulates hepatic expression of inflammatory chemokine, cytokine-induced neutrophil chemoattractant-1, in scurvy-prone ODS rats. | 2006 Feb |
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| Retinoic acid and ascorbic acid act synergistically in inhibiting human breast cancer cell proliferation. | 2006 Jul |
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| Ascorbic acid differentially modulates the induction of heme oxygenase-1, NAD(P)H:quinone oxidoreductase 1 and glutathione S-transferase Ya by As(3+), Cd(2+) and Cr(6+). | 2007 Feb 8 |
Patents
Sample Use Guides
Ascorbic acid (vitamin c) is usually administered orally. When oral administration is not feasible or when malabsorption is suspected, the drug may be administered IM, IV, or subcutaneously. When given parenterally, utilization of the vitamin reportedly is best after IM administration and that is the preferred parenteral route.
For intravenous injection, dilution into a large volume parenteral such as Normal Saline, Water for Injection, or Glucose is recommended to minimize the adverse reactions associated with intravenous injection.
The average protective dose of vitamin C for adults is 70 to 150 mg daily. In the presence of scurvy, doses of 300 mg to 1 g daily are recommended. However, as much as 6 g has been administered parenterally to normal adults without evidence of toxicity.
To enhance wound healing, doses of 300 to 500 mg daily for a week or ten days both preoperatively and postoperatively are generally considered adequate, although considerably larger amounts have been recommended. In the treatment of burns, doses are governed by the extent of tissue injury. For severe burns, daily doses of 1 to 2 g are recommended. In other conditions in which the need for vitamin C is increased, three to five times the daily optimum allowances appear to be adequate.
Parenteral drug products should be inspected visually for particulate matter and discoloration prior to administration, whenever the solution and container permit.
Route of Administration:
Other
cell-derived decellularized extracellular matrix (dECM) with 250 µM of L-ascorbic acid phosphate (AA) treatment for 10 d had better rejuvenation in chondrogenic capacity if the deposited cells were from passage 2 rather than passage 5, despite no significant difference in matrix stiffness. In the dose regimen study, we found that dECMs deposited by varied concentrations of AA yielded expanded cells with higher proliferation capacity despite lower expression levels of stem cell related surface markers. Compared to cells expanded on tissue culture polystyrene, those on dECM exhibited greater chondrogenic potential, particularly for the dECMs with 50 µM and 250 µM of AA treatment. With the supplementation of ethyl-3,4-dihydroxybenzoate (EDHB), an inhibitor targeting procollagen synthesis, the dECM with 50 µM of AA treatment exhibited a dramatic decrease in the rejuvenation effect of expanded cell chondrogenic potential at both mRNA and protein levels despite no significant difference in matrix stiffness.
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NCI_THESAURUS |
C68507
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836SJG51DR
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836SJG51DR
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100000183888
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C87289
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10990876
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1364501
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81687
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C011669
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66170-10-3
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DTXSID601014965
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
