Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H8O6 |
| Molecular Weight | 176.1241 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
InChI
InChIKey=CIWBSHSKHKDKBQ-JLAZNSOCSA-N
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/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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| Quinine blindness. | 1992 Dec |
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| Effect of antioxidants (vitamin C, E and turmeric extract) on methimazole induced hypothyroidism in rats. | 2002 Jun |
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| Effect of vitamin C supplementation on oxidative DNA damage in an experimental model of lead-induced hypertension. | 2003 |
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| Ascorbic acid enhances differentiation of embryonic stem cells into cardiac myocytes. | 2003 Apr 15 |
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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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| Vitamin C as an antioxidant: evaluation of its role in disease prevention. | 2003 Feb |
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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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| Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme. | 2003 Jun |
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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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| 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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| Vitamin C rescues in part the effects of nitrofen on cultured human pneumocytes. | 2004 Apr |
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| Incorporation of an oxygen from water into troglitazone quinone by cytochrome P450 and myeloperoxidase. | 2004 Apr |
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| Ascorbic acid treatment corrects the phenotype of a mouse model of Charcot-Marie-Tooth disease. | 2004 Apr |
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| Ascorbic acid responsive genes during neuronal differentiation of embryonic stem cells. | 2004 Aug 26 |
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| Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
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| Cell cycle arrest and autoschizis in a human bladder carcinoma cell line following Vitamin C and Vitamin K3 treatment. | 2004 Jan 15 |
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| Micronutrient deficiencies as predisposing factors for hypertension in lacto-vegetarian Indian adults. | 2004 Jun |
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| Norepinephrine induces apoptosis in neonatal rat cardiomyocytes through a reactive oxygen species-TNF alpha-caspase signaling pathway. | 2004 Jun 1 |
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| Effect of ascorbic acid supplementation on testicular steroidogenesis and germ cell death in cadmium-treated male rats. | 2004 Jun 30 |
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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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| Effect of antioxidant flavanone, naringenin, from Citrus junoson neuroprotection. | 2004 Mar 24 |
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| Involvement of glycosylphosphatidylinositol-linked ceruloplasmin in the copper/zinc-nitric oxide-dependent degradation of glypican-1 heparan sulfate in rat C6 glioma cells. | 2004 Mar 26 |
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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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| 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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| Anti-angiogenesis efficacy of the garlic ingredient alliin and antioxidants: role of nitric oxide and p53. | 2005 |
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| Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia. | 2005 Aug |
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| [Effect of compound salvia injection on nitrate ester tolerance]. | 2005 Jan |
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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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| 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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| 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 |
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| Megaloblastic anaemia: response to Amples A and B (folic acid, vitamin B12 (Cyanocobalamin), niacin and vitamin C)--a case report. | 2005 Oct-Dec |
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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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| 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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| Synergistic interactions of ferulic acid with ascorbic acid: its cardioprotective role during isoproterenol induced myocardial infarction in rats. | 2006 Feb |
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| Ascorbic acid and alpha-tocopherol down-regulate apolipoprotein A-I gene expression in HepG2 and Caco-2 cell lines. | 2006 Feb |
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| Morphology and DNA degeneration during autoschizic cell death in bladder carcinoma T24 cells induced by ascorbate and menadione treatment. | 2006 Jan |
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| Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. | 2006 Jul |
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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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| Phenotypes of mice lacking extracellular superoxide dismutase and copper- and zinc-containing superoxide dismutase. | 2006 Mar 17 |
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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 |
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| Ascorbic acid enhances the inhibitory effect of aspirin on neuronal cyclooxygenase-2-mediated prostaglandin E2 production. | 2006 May |
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| Impact of diabetes mellitus on the relationships between iron-, inflammatory- and oxidative stress status. | 2006 Nov-Dec |
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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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N0000193618
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INS-300
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21 CFR 862.1095
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A11GB01
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21 CFR 310.727
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1904-2
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176783
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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D001205
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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DB00126
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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769
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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218455
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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CHEMBL196
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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m2089
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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PRIMARY | Merck Index | ||
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1151
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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PRIMARY | RxNorm | ||
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Vitamin C
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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C285
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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ASCORBIC ACID
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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PRIMARY | Description: Colourless crystals or a white or almost white, crystalline powder; odourless or almost odourless. Solubility: Freely soluble in water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Antiscorbutic. Storage: Ascorbic acid should be kept in a tightly closed, non-metallic container, protected from light. Additional information: Ascorbic acid in solution deteriorates rapidly in contact with air; it has an acid taste. Even in the absenceof light, Ascorbic acid is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Ascorbic acid contains not less than 99.0% and not more than 100.5% of C6H8O6. | ||
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1370460
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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ALTERNATIVE | |||
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54670067
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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1043003
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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33832
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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38290
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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4072
Created by
admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
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