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
Molecular Formula | C6H8O6 |
Molecular Weight | 176.1241 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9389750 | https://www.ncbi.nlm.nih.gov/pubmed/19162177
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23183299
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: WP408 |
|||
Target ID: CHEMBL1991 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15254232 |
|||
Target ID: CHEMBL3476 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15254232 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: http://www.rxlist.com/ascorbic-acid-drug.htm |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16305291/ Page: 4.0 |
moderate | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8269614/ Page: 4.0 |
yes |
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 |
|
Induction of oxidative stress by glutathione depletion causes severe hypertension in normal rats. | 2000 Jul |
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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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Mutagenicity of food-derived carcinogens and the effect of antioxidant vitamins. | 2002 |
|
Activation of Rac1 and the p38 mitogen-activated protein kinase pathway in response to arsenic trioxide. | 2002 Nov 22 |
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Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
|
Metalloenzyme-like activity of Alzheimer's disease beta-amyloid. Cu-dependent catalytic conversion of dopamine, cholesterol, and biological reducing agents to neurotoxic H(2)O(2). | 2002 Oct 25 |
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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 |
|
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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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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Nelfinavir induces necrosis of 3T3F44-2A adipocytes by oxidative stress. | 2004 Dec 15 |
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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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Micronutrient deficiencies as predisposing factors for hypertension in lacto-vegetarian Indian adults. | 2004 Jun |
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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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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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Vitamin C controls the cystic fibrosis transmembrane conductance regulator chloride channel. | 2004 Mar 9 |
|
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 |
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[Effect of compound salvia injection on nitrate ester tolerance]. | 2005 Jan |
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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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Morphology and DNA degeneration during autoschizic cell death in bladder carcinoma T24 cells induced by ascorbate and menadione treatment. | 2006 Jan |
|
Phenotypes of mice lacking extracellular superoxide dismutase and copper- and zinc-containing superoxide dismutase. | 2006 Mar 17 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27508528
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
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by
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on
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Record UNII |
PQ6CK8PD0R
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Record Status |
Validated (UNII)
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Record Version |
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C275
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3135 (Number of products:3731)
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WHO-ESSENTIAL MEDICINES LIST |
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N0000193618
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JECFA EVALUATION |
INS-300
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EU-Orphan Drug |
EU/3/17/1832
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CFR |
21 CFR 862.1095
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A11GB01
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2644 (Number of products:145)
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678719
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21 CFR 101.78
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21 CFR 310.727
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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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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (TITRATION)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> ENANTIOMER | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Nutritional value per 100 g (3.5 oz) - 89.2 mg (107%)
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.35.pdf
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