Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H19N7O6 |
Molecular Weight | 441.3975 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=N2)C(=O)N1
InChI
InChIKey=OVBPIULPVIDEAO-LBPRGKRZSA-N
InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1
Molecular Formula | C19H19N7O6 |
Molecular Weight | 441.3975 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugs.com/pro/folic-acid.htmlCurator's Comment: description was created based on several sources, including
http://pubs.acs.org/doi/abs/10.1021/ja01853a512 | https://www.ncbi.nlm.nih.gov/pubmed/28031963 | https://www.ncbi.nlm.nih.gov/pubmed/1560436
Sources: https://www.drugs.com/pro/folic-acid.html
Curator's Comment: description was created based on several sources, including
http://pubs.acs.org/doi/abs/10.1021/ja01853a512 | https://www.ncbi.nlm.nih.gov/pubmed/28031963 | https://www.ncbi.nlm.nih.gov/pubmed/1560436
Folic Acid is a B complex vitamin containing a pteridine moiety linked by a methylene bridge to para-aminobenzoic acid, which is joined by a peptide linkage to glutamic acid. Conjugates of Folic Acid are present in a wide variety of foods, particularly liver, kidneys, yeast and leafy green vegetables. Commercially available Folic Acid is prepared synthetically. Folic Acid occurs as a yellow or yellowish-orange crystalline powder and is very slightly soluble in water and insoluble in alcohol. Aqueous solutions of Folic Acid are heat sensitive and rapidly decompose in the presence of light and/or riboflavin; solutions should be stored in a cool place protected from light. Folic Acid is effective in the treatment of megaloblastic anemias due to a deficiency of Folic Acid (as may be seen in tropical or nontropical sprue) and in anemia of nutritional origin, pregnancy, infancy, or childhood. Folic Acid is relatively nontoxic in man. Rare instances of allergic responses to Folic Acid preparations have been reported and have included erythema, skin rash, itching, general malaise, and respiratory difficulty due to bronchospasm. Endocyte is developing an intravenous (IV) formulation of folic acid, called Neocepri®, which is intended for the diagnosis of positive folate receptor-positive status in patients with ovarian cancer when administered prior to the radioactive medicine, technetium Tc99m Etarfolatide. The benefits of Neocepri® are its ability to reduce the background activity observed on single photon emission computed tomography (SPECT) imaging in most normal, nontarget tissues (e.g. intestines, liver, kidney, spleen), thereby improving the image quality of the scans. The product had been granted orphan drug designation in the EU. Endocyte had filed a conditional marketing authorization application (CMA) with the European Medicines Agency (EMA) for Neocepri®.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006760 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27131640 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | FOLVITE Approved UseIndications and Usage. Folic Acid is effective in the treatment of megaloblastic anemias due to a deficiency of Folic Acid (as may be seen in tropical or nontropical sprue) and in anemia of nutritional origin, pregnancy, infancy, or childhood. Launch Date1947 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18551467/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
76 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18551467/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.93 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18551467/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
Title | Date | PubMed |
---|---|---|
Harmful effect of megadoses of vitamins: electroencephalogram abnormalities and seizures induced by intravenous folate in drug-treated epileptics. | 1975 Jan |
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Exocrine pancreatic insufficiency in tropical sprue. | 2001 |
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Folate and vitamin B6 from diet and supplements in relation to risk of coronary heart disease among women. | 2001 |
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A bifunctional dihydrofolate synthetase--folylpolyglutamate synthetase in Plasmodium falciparum identified by functional complementation in yeast and bacteria. | 2001 Feb |
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Cloning, expression, genomic localization, and enzymatic activities of the mouse homolog of prostate-specific membrane antigen/NAALADase/folate hydrolase. | 2001 Feb |
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No effect of phenobarbital pretreatment of rats on methotrexate pharmacokinetics in the isolated liver perfused in a single-pass way. | 2001 Feb |
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Vitamin Intervention for Stroke Prevention (VISP) trial: rationale and design. | 2001 Feb |
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Analysis of uracil DNA glycosylase in human colorectal cancer. | 2001 Feb |
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Intake of vegetables rich in carotenoids and risk of coronary heart disease in men: The Physicians' Health Study. | 2001 Feb |
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Lowered weight gain during pregnancy and risk of neural tube defects among offspring. | 2001 Feb |
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Folate reception by vegetative Dictyostelium discoideum amoebae: distribution of receptors and trafficking of ligand. | 2001 Feb |
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Homocysteine, its metabolites, and B-group vitamins in renal transplant patients. | 2001 Feb |
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Is there a role of cyclosporine A on total homocysteine export from human renal proximal tubular epithelial cells? | 2001 Feb |
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Effect of MTHFR genotypes and hyperhomocysteinemia on patient and graft survival in kidney transplant recipients. | 2001 Feb |
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Treatment of hyperhomocysteinemia in hemodialysis patients and renal transplant recipients. | 2001 Feb |
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Recent insights into the molecular genetics of the homocysteine metabolism. | 2001 Feb |
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Methylenetetrahydrofolate reductase genotypes and predisposition to atherothrombotic disease; evidence that all three MTHFR C677T genotypes confer different levels of risk. | 2001 Feb |
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Long-term safety and efficacy of a cholesterol-lowering diet in children with elevated low-density lipoprotein cholesterol: seven-year results of the Dietary Intervention Study in Children (DISC). | 2001 Feb |
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C677T variant form at the MTHFR gene and CL/P: a risk factor for mothers? | 2001 Feb 1 |
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It's just a vitamin.. | 2001 Feb 1 |
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Lack of clinical utility of folate levels in the evaluation of macrocytosis or anemia. | 2001 Feb 1 |
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Bioactivity of [6R]-5-formyltetrahydrofolate, an unusual isomer, in humans and Enterococcus hirae, and cytochrome c oxidation of 10-formytetrahydrofolate to 10-formyldihydrofolate. | 2001 Feb 15 |
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Transcobalamin codon 259 polymorphism in HT-29 and Caco-2 cells and in Caucasians: relation to transcobalamin and homocysteine concentration in blood. | 2001 Feb 15 |
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Phase I dose-escalation and pharmacokinetic study of a novel folate analogue AG2034. | 2001 Feb 2 |
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Supplementation of atherogenic diet with B vitamins does not prevent atherosclerosis or vascular dysfunction in monkeys. | 2001 Feb 20 |
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[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options]. | 2001 Jan |
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SLATE: a method for the superposition of flexible ligands. | 2001 Jan |
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[Theoretical construction of chemotherapeutic tactics for advanced or recurrent gastrointestinal carcinoma]. | 2001 Jan |
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Characterization of three genes encoding enzymes of the folate biosynthetic pathway in Plasmodium falciparum. | 2001 Jan |
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Homocysteine: a new cardiac risk factor? | 2001 Jan |
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Ascertainment of pregnancies terminated because of birth defects: effect on completeness of adding a new source of data. | 2001 Jan |
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Nutritional status of folate and colon cancer risk: evidence from NHANES I epidemiologic follow-up study. | 2001 Jan |
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Lp(a) lipoprotein--an independent risk factor for coronary heart disease after menopause. | 2001 Jan |
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Antimicrobial activities of dihydrofolate reductase inhibitors, used singly or in combination with dapsone, against Mycobacterium ulcerans. | 2001 Jan |
|
Vitamin B12 deficiency in children and adolescents. | 2001 Jan |
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Long-term reduction of plasma homocysteine levels by super-flux dialyzers in hemodialysis patients. | 2001 Jan |
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Rapid communication: L-folinic acid versus folic acid for the treatment of hyperhomocysteinemia in hemodialysis patients. | 2001 Jan |
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Inhibition of thymidine synthesis by folate analogues induces a Fas-Fas ligand-independent deletion of superantigen-reactive peripheral T cells. | 2001 Jan |
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Maternal plasma homocysteine levels in women with preterm premature rupture of membranes. | 2001 Jan |
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Retroviral expression of Escherichia coli thymidylate synthase cDNA confers high-level antifolate resistance to hematopoietic cells. | 2001 Jan 1 |
|
Comparison of the bacterial flora of the duodenum in healthy cats and cats with signs of gastrointestinal tract disease. | 2001 Jan 1 |
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Factors that influence the penetration of methotrexate through solid tissue. | 2001 Jan 1 |
|
Folic acid and miscarriage: an unjustified link. | 2001 Jan 15 |
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Dietary intake of selected micronutrients and breast-cancer risk. | 2001 Jan 15 |
|
Cross-talk between steroid-receptor-mediated and cell-membrane-receptor-mediated signalling pathways results in the in vivo modulation of c-Met and ornithine decarboxylase gene expression in mouse kidney. | 2001 Jan 15 |
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Diet-induced hyperhomocysteinemia exacerbates neointima formation in rat carotid arteries after balloon injury. | 2001 Jan 2 |
|
Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage. | 2001 Jan 25 |
|
Passive and iontophoretic transdermal penetration of methotrexate. | 2001 Jan 5 |
|
[Folates, vitamin B12, homocysteine and neural tube defects]. | 2001 Jan-Feb |
|
Hyperhomocysteinemia and hypercholesterolemia associated with hypothyroidism in the third US National Health and Nutrition Examination Survey. | 2001 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/folic-acid.html
Usual Adult Dose for Megaloblastic Anemia: 1 mg orally, intramuscularly, subcutaneously or IV once a day.
Nutritional Supplementation (Recommended daily allowance): Males: 400 mkg/day, Females: 400-800 mkg/day, Pregnant women: 600 mkg/day, Nursing women: 500 mkg/day, Upper limit: 1 mg/day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1560436
Duplicate cultures of L1210 murine leukemia cells were exposed to increasing concentrations of folic acid (up to 10mM). Tumor Cell Growth was assayed after 48 h.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:31:37 GMT 2025
by
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on
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Record UNII |
935E97BOY8
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Record Status |
Validated (UNII)
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WHO-VATC |
QB03AE01
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WHO-ESSENTIAL MEDICINES LIST |
10.1 (FER/FOL)
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LOINC |
2283-0
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CFR |
21 CFR 102.23
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LIVERTOX |
NBK548804
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2284-8
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WHO-ATC |
B03BB51
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B03AE01
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55859-3
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25415-1
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DSLD |
189 (Number of products:374)
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14732-2
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14903-9
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CFR |
21 CFR 862.1295
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CFR |
21 CFR 172.345
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WHO-VATC |
QB03AE02
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WHO-VATC |
QB03BB01
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DSLD |
2383 (Number of products:2319)
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CFR |
21 CFR 101.79
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WHO-ATC |
B03AE02
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LOINC |
27088-4
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49264-5
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50039-7
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2282-2
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DSLD |
3522 (Number of products:75)
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DSLD |
3132 (Number of products:6858)
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NCI_THESAURUS |
C1444
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14731-4
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35210-4
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14733-0
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WHO-ESSENTIAL MEDICINES LIST |
10.1
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WHO-ATC |
B03BB01
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62356
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935E97BOY8
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2002
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1231
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3073
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C510
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6037
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CHEMBL1622
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176842
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FOLIC ACID
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PRIMARY | Description: A yellow or yellowish orange, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; practically insoluble in ethanol (~750 g/l) TS, acetone R and ether R. Category: Haemopoietic. Storage: Folic acid should be kept in a well-closed container, protected from light. Definition: Folic acid contains not less than 96.0% and not more than 102.0% of C19H19N7O6, calculated with reference to the anhydrous substance. | ||
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200-419-0
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935E97BOY8
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59-30-3
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1286005
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67011
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m5518
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100000085634
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4511
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37445
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D005492
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27470
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FOLIC ACID
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DB00158
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68
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Related Record | Type | Details | ||
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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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SOLVATE->ANHYDROUS |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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TRANSPORTER -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Levomefolate calcium is structurally identical to L-5-methyltetrahydrofolate (L-5-methyl-THF), a metabolite of vitamin B9
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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