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
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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| Copper-dependent formation of disulfide-linked dimer of S100B protein. | 2000 Feb 15 |
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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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| Inhibition of human plasmin activity using humic acids with arsenic. | 2001 Jun 12 |
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| Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
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| Ascorbic acid enhances differentiation of embryonic stem cells into cardiac myocytes. | 2003 Apr 15 |
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| Ascorbic acid and alpha-tocopherol as potent modulators on arsenic induced toxicity in mitochondria. | 2003 Jul |
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| Arsenic trioxide induces apoptosis in cells of MOLT-4 and its daunorubicin-resistant cell line via depletion of intracellular glutathione, disruption of mitochondrial membrane potential and activation of caspase-3. | 2003 Jul |
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| Lead-induced downregulation of soluble guanylate cyclase in isolated rat aortic segments mediated by reactive oxygen species and cyclooxygenase-2. | 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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| Modulation of TNF-alpha-induced ICAM-1 expression, NO and H2O2 production by alginate, allicin and ascorbic acid in human endothelial cells. | 2003 Mar |
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| Up-regulation and polarized expression of the sodium-ascorbic acid transporter SVCT1 in post-confluent differentiated CaCo-2 cells. | 2003 Mar 14 |
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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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| Vitamin C rescues in part the effects of nitrofen on cultured human pneumocytes. | 2004 Apr |
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| Ascorbic acid responsive genes during neuronal differentiation of embryonic stem cells. | 2004 Aug 26 |
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| [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 |
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| Vitamin C and vitamin E protect the rat testes from cadmium-induced reactive oxygen species. | 2004 Feb 29 |
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| 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 |
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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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| Vitamin C controls the cystic fibrosis transmembrane conductance regulator chloride channel. | 2004 Mar 9 |
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| Does supplemental vitamin C increase cardiovascular disease risk in women with diabetes? | 2004 Nov |
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| 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 |
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| Changes of gene expression profiles during neuronal differentiation of central nervous system precursors treated with ascorbic acid. | 2004 Oct 1 |
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| [The role of reactive oxygen species in N-[4-hydroxyphenyl] retinamide induced apoptosis in bladder cancer cell lineT24]. | 2005 Jun |
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| Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). | 2005 May |
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| Mismatch repair proteins are activators of toxic responses to chromium-DNA damage. | 2005 May |
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| Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes. | 2006 |
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| Ascorbate depletion mediates up-regulation of hypoxia-associated proteins by cell density and nickel. | 2006 Apr 1 |
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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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| 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 |
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| Antioxidant effect of ascorbic acid on PCB (Aroclor 1254) induced oxidative stress in hypothalamus of albino rats. | 2006 Mar |
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| 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 |
|
| Impact of diabetes mellitus on the relationships between iron-, inflammatory- and oxidative stress status. | 2006 Nov-Dec |
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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167162
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23313-12-4
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DTXSID00945987
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VKX4PM7299
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54679073
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
