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=NC=C(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N=C2C(=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 |
Doses
Dose | Population | Adverse events |
---|---|---|
3 mg 1 times / day steady, oral (min) Highest studied dose Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: |
healthy, adult n = 480526 Health Status: healthy Condition: pregnant Age Group: adult Sex: F Population Size: 480526 Sources: |
Other AEs: Autism spectrum disorder... |
400 ug 1 times / day steady, oral Recommended Dose: 400 ug, 1 times / day Route: oral Route: steady Dose: 400 ug, 1 times / day Sources: |
healthy, adult n = 1257 Health Status: healthy Condition: pregnant Age Group: adult Sex: F Population Size: 1257 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Autism spectrum disorder | 6.8% | 3 mg 1 times / day steady, oral (min) Highest studied dose Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: |
healthy, adult n = 480526 Health Status: healthy Condition: pregnant Age Group: adult Sex: F Population Size: 480526 Sources: |
PubMed
Title | Date | PubMed |
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Folic acid-induced acute renal failure in the the rat: morphological studies. | 1976 Oct |
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[Reduced number of neural tube defects after folic acid supplementation in China]. | 1999 Dec 1 |
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Weekly lometrexol with daily oral folic acid is appropriate for phase II evaluation. | 2000 |
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[Sulphur amino acids, vitamin B12 and folic acid in children with chronic renal failure]. | 2000 Apr |
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Folic acid antagonists during pregnancy and the risk of birth defects. | 2000 Nov 30 |
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Up-regulation of galectin-3 in acute renal failure of the rat. | 2000 Sep |
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Conversion of 5-formyltetrahydrofolic acid to 5-methyltetrahydrofolic acid is unimpaired in folate-adequate persons homozygous for the C677T mutation in the methylenetetrahydrofolate reductase gene. | 2000 Sep |
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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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Folic acid and neural tube defects. | 2001 |
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Folic acid, vitamins B6 and B12: relation to homocysteine and cardiovascular disease. | 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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Hypercoagulable thrombophilic defects and hyperhomocysteinemia in patients with recurrent pregnancy loss. | 2001 Feb |
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Low seminal plasma folate concentrations are associated with low sperm density and count in male smokers and nonsmokers. | 2001 Feb |
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Analysis of uracil DNA glycosylase in human colorectal cancer. | 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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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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Selected food intake and risk of multiple pregnancies. | 2001 Feb |
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Homocysteine and coronary heart disease in the Caerphilly cohort: a 10 year follow up. | 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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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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[Theoretical construction of chemotherapeutic tactics for advanced or recurrent gastrointestinal carcinoma]. | 2001 Jan |
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Gastric tube graft interposition as an oesophageal substitute. | 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 |
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Vitamin B12 deficiency in children and adolescents. | 2001 Jan |
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Hyperhomocysteinemia and oxidative stress in ischemic stroke. | 2001 Jan |
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Plasma homocysteine concentrations in the acute and convalescent periods of atherothrombotic stroke. | 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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Diagnosis and treatment of hyperhomocysteinemia. | 2001 Jan |
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Hyperhomocysteinaemia in young adults is not associated with impaired endothelial function. | 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 |
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Factors that influence the penetration of methotrexate through solid tissue. | 2001 Jan 1 |
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Impact of the reduced folate carrier on the accumulation of active thiamin metabolites in murine leukemia cells. | 2001 Jan 12 |
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Folic acid and miscarriage: an unjustified link. | 2001 Jan 15 |
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Physical activity and risk for cardiovascular events in diabetic women. | 2001 Jan 16 |
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Passive and iontophoretic transdermal penetration of methotrexate. | 2001 Jan 5 |
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Hyperhomocysteinemia is associated with venous thrombosis in patients with short bowel syndrome. | 2001 Jan-Feb |
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Antisense modulation of 5,10-methylenetetrahydrofolate reductase expression produces neural tube defects in mouse embryos. | 2001 Jan-Feb |
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Hyperhomocysteinemia and hypercholesterolemia associated with hypothyroidism in the third US National Health and Nutrition Examination Survey. | 2001 Mar |
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Knowledge on periconceptional use of folic acid in women of British Columbia. | 2001 Mar-Apr |
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
Fri Dec 15 16:34:16 GMT 2023
by
admin
on
Fri Dec 15 16:34:16 GMT 2023
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Record UNII |
935E97BOY8
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Record Status |
Validated (UNII)
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Record Version |
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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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LOINC |
2284-8
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WHO-ATC |
B03BB51
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WHO-ATC |
B03AE01
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LOINC |
55859-3
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25415-1
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DSLD |
189 (Number of products:374)
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LOINC |
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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LOINC |
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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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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m5518
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100000085634
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4511
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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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TRANSPORTER -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Nutritional value per 100 g (3.5 oz) - 63 ug (16%)
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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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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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