Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H9O9P |
| Molecular Weight | 256.104 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(OC(=O)C(OP(O)(O)=O)=C1O)[C@@H](O)CO
InChI
InChIKey=MIJPAVRNWPDMOR-ZAFYKAAXSA-N
InChI=1S/C6H9O9P/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)/t2-,4+/m0/s1
| Molecular Formula | C6H9O9P |
| Molecular Weight | 256.104 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|||
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 |
|||
| 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 |
|
| Vitamin C rescues in part the effects of nitrofen on cultured human pneumocytes. | 2004 Apr |
|
| Incorporation of an oxygen from water into troglitazone quinone by cytochrome P450 and myeloperoxidase. | 2004 Apr |
|
| Ascorbic acid treatment corrects the phenotype of a mouse model of Charcot-Marie-Tooth disease. | 2004 Apr |
|
| Ascorbic acid responsive genes during neuronal differentiation of embryonic stem cells. | 2004 Aug 26 |
|
| Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
|
| Nelfinavir induces necrosis of 3T3F44-2A adipocytes by oxidative stress. | 2004 Dec 15 |
|
| [Ascorbic acid inhibits the formation and function of osteoclasts from RAW264.7 cells induced by receptor activated nuclear factor kappaB ligand in vitro]. | 2004 Dec 17 |
|
| Vitamin C and vitamin E protect the rat testes from cadmium-induced reactive oxygen species. | 2004 Feb 29 |
|
| Micronutrient deficiencies as predisposing factors for hypertension in lacto-vegetarian Indian adults. | 2004 Jun |
|
| Alteration of cellular phenotype and responses to oxidative stress by manganese superoxide dismutase and a superoxide dismutase mimic in RWPE-2 human prostate adenocarcinoma cells. | 2004 Jun |
|
| Norepinephrine induces apoptosis in neonatal rat cardiomyocytes through a reactive oxygen species-TNF alpha-caspase signaling pathway. | 2004 Jun 1 |
|
| Effect of ascorbic acid supplementation on testicular steroidogenesis and germ cell death in cadmium-treated male rats. | 2004 Jun 30 |
|
| Copper ions and hypochlorite are mainly responsible for oxidative inactivation of paraoxon-hydrolyzing activity in human high density lipoprotein. | 2004 Mar 7 |
|
| Does supplemental vitamin C increase cardiovascular disease risk in women with diabetes? | 2004 Nov |
|
| Cytoprotection by bcl-2 gene transfer against ischemic liver injuries together with repressed lipid peroxidation and increased ascorbic acid in livers and serum. | 2004 Nov 15 |
|
| Changes of gene expression profiles during neuronal differentiation of central nervous system precursors treated with ascorbic acid. | 2004 Oct 1 |
|
| Effects of various antioxidants on endotoxin-induced lung injury and gene expression: mRNA expressions of MnSOD, interleukin-1beta and iNOS. | 2004 Sep 30 |
|
| 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 |
|
| Anti-angiogenesis efficacy of the garlic ingredient alliin and antioxidants: role of nitric oxide and p53. | 2005 |
|
| The amyloid precursor protein (APP) of Alzheimer disease and its paralog, APLP2, modulate the Cu/Zn-Nitric Oxide-catalyzed degradation of glypican-1 heparan sulfate in vivo. | 2005 Apr 8 |
|
| Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia. | 2005 Aug |
|
| [Effect of compound salvia injection on nitrate ester tolerance]. | 2005 Jan |
|
| Antioxidant vitamin supplementation reduces benzo(a)pyrene-DNA adducts and potential cancer risk in female smokers. | 2005 Jan |
|
| [The role of reactive oxygen species in N-[4-hydroxyphenyl] retinamide induced apoptosis in bladder cancer cell lineT24]. | 2005 Jun |
|
| Ascorbic acid inhibits osteoclastogenesis of RAW264.7 cells induced by receptor activated nuclear factor kappaB ligand (RANKL) in vitro. | 2005 Mar |
|
| Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). | 2005 May |
|
| Mismatch repair proteins are activators of toxic responses to chromium-DNA damage. | 2005 May |
|
| Studies on the protective role of vitamin C and E against polychlorinated biphenyl (Aroclor 1254)--induced oxidative damage in Leydig cells. | 2005 Nov |
|
| Relationship of bone morphogenetic protein expression during osteoblast differentiation to wild type p53. | 2005 Nov |
|
| Iron-ascorbic acid-induced oxidant stress and its quenching by paraoxonase 1 in HDL and the liver: comparison between humans and rats. | 2005 Oct 1 |
|
| Inhibition of iNOS gene expression by quercetin is mediated by the inhibition of IkappaB kinase, nuclear factor-kappa B and STAT1, and depends on heme oxygenase-1 induction in mouse BV-2 microglia. | 2005 Oct 3 |
|
| Megaloblastic anaemia: response to Amples A and B (folic acid, vitamin B12 (Cyanocobalamin), niacin and vitamin C)--a case report. | 2005 Oct-Dec |
|
| Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes. | 2006 |
|
| Ascorbate depletion mediates up-regulation of hypoxia-associated proteins by cell density and nickel. | 2006 Apr 1 |
|
| Ascorbic acid deficiency stimulates hepatic expression of inflammatory chemokine, cytokine-induced neutrophil chemoattractant-1, in scurvy-prone ODS rats. | 2006 Feb |
|
| Synergistic interactions of ferulic acid with ascorbic acid: its cardioprotective role during isoproterenol induced myocardial infarction in rats. | 2006 Feb |
|
| Ascorbic acid and alpha-tocopherol down-regulate apolipoprotein A-I gene expression in HepG2 and Caco-2 cell lines. | 2006 Feb |
|
| Morphology and DNA degeneration during autoschizic cell death in bladder carcinoma T24 cells induced by ascorbate and menadione treatment. | 2006 Jan |
|
| Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. | 2006 Jul |
|
| Retinoic acid and ascorbic acid act synergistically in inhibiting human breast cancer cell proliferation. | 2006 Jul |
|
| Combined antioxidant (beta-carotene, alpha-tocopherol and ascorbic acid) supplementation increases the levels of lung retinoic acid and inhibits the activation of mitogen-activated protein kinase in the ferret lung cancer model. | 2006 Jul |
|
| Antioxidant effect of ascorbic acid on PCB (Aroclor 1254) induced oxidative stress in hypothalamus of albino rats. | 2006 Mar |
|
| Phenotypes of mice lacking extracellular superoxide dismutase and copper- and zinc-containing superoxide dismutase. | 2006 Mar 17 |
|
| Antioxidant supplementation with or without B-group vitamins after acute ischemic stroke: a randomized controlled trial. | 2006 Mar-Apr |
|
| Attenuation of abnormalities in the lipid metabolism during experimental myocardial infarction induced by isoproterenol in rats: beneficial effect of ferulic acid and ascorbic acid. | 2006 May |
|
| Ascorbic acid enhances the inhibitory effect of aspirin on neuronal cyclooxygenase-2-mediated prostaglandin E2 production. | 2006 May |
|
| N-(4-hydroxyphenyl)retinamide-induced apoptosis triggered by reactive oxygen species is mediated by activation of MAPKs in head and neck squamous carcinoma cells. | 2006 May 4 |
|
| Impact of diabetes mellitus on the relationships between iron-, inflammatory- and oxidative stress status. | 2006 Nov-Dec |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:39:15 GMT 2023
by
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on
Fri Dec 15 19:39:15 GMT 2023
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| Record UNII |
VKX4PM7299
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| Record Status |
Validated (UNII)
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| Record Version |
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VKX4PM7299
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