Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H19N7O6 |
Molecular Weight | 441.3982 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc(ccc1C(=O)N[C@@]([H])(CCC(=O)O)C(=O)O)NCc2cnc3c(c(nc(=N)[nH]3)O)n2
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
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 Date-7.1254082E11 |
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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Harmful effect of megadoses of vitamins: electroencephalogram abnormalities and seizures induced by intravenous folate in drug-treated epileptics. | 1975 Jan |
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Folic acid antagonists during pregnancy and the risk of birth defects. | 2000 Nov 30 |
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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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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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Determinants of changes in plasma homocysteine in hyperthyroidism and hypothyroidism. | 2001 Feb |
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Homocysteine metabolism in renal failure. | 2001 Feb |
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The folate cycle and disease in humans. | 2001 Feb |
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Changes in markers of anemia and iron metabolism and how they are influenced by antianemics in postpartum period. | 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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Supplementation of atherogenic diet with B vitamins does not prevent atherosclerosis or vascular dysfunction in monkeys. | 2001 Feb 20 |
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SLATE: a method for the superposition of flexible ligands. | 2001 Jan |
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Preconceptual folic acid: opportunity for preconceptual counseling offers opportunity to help prevent neural tube defects. | 2001 Jan |
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Effects of methionine loading on plasma and erythrocyte sulphur amino acids and sulph-hydryls before and after co-factor supplementation in haemodialysis patients. | 2001 Jan |
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Diet and cancer: one view at the start of the millennium. | 2001 Jan |
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Homocysteine: a new cardiac risk factor? | 2001 Jan |
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Gastric tube graft interposition as an oesophageal substitute. | 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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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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Maternal plasma homocysteine levels in women with preterm premature rupture of membranes. | 2001 Jan |
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Diagnosis and treatment of hyperhomocysteinemia. | 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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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 |
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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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Dietary intake of selected micronutrients and breast-cancer risk. | 2001 Jan 15 |
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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 |
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The effect of folate deficiency on the cytotoxic and mutagenic responses to ethyl methanesulfonate in human lymphoblastoid cell lines that differ in p53 status. | 2001 Jan 25 |
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Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage. | 2001 Jan 25 |
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Synthesis and evaluation of pteroic acid-conjugated nitroheterocyclic phosphoramidates as folate receptor-targeted alkylating agents. | 2001 Jan 4 |
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Passive and iontophoretic transdermal penetration of methotrexate. | 2001 Jan 5 |
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[Folates, vitamin B12, homocysteine and neural tube defects]. | 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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Human 5-aminoimidazole-4-carboxamide ribonucleotide transformylase/inosine 5'-monophosphate cyclohydrolase. A bifunctional protein requiring dimerization for transformylase activity but not for cyclohydrolase activity. | 2001 Mar 16 |
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The basal promoters for the human reduced folate carrier gene are regulated by a GC-box and a cAMP-response element/AP-1-like element. Basis for tissue-specific gene expression. | 2001 Mar 2 |
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Repression of human reduced folate carrier gene expression by wild type p53. | 2001 Mar 23 |
|
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.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QB03AE01
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WHO-ESSENTIAL MEDICINES LIST |
10.1 (FER/FOL)
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admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
2283-0
Created by
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CFR |
21 CFR 102.23
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LIVERTOX |
432
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LOINC |
2284-8
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WHO-ATC |
B03BB51
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WHO-ATC |
B03AE01
Created by
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LOINC |
55859-3
Created by
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LOINC |
25415-1
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DSLD |
189 (Number of products:374)
Created by
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LOINC |
14732-2
Created by
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LOINC |
14903-9
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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CFR |
21 CFR 862.1295
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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CFR |
21 CFR 172.345
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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WHO-VATC |
QB03AE02
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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WHO-VATC |
QB03BB01
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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DSLD |
2383 (Number of products:2319)
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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CFR |
21 CFR 101.79
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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WHO-ATC |
B03AE02
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
27088-4
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
49264-5
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
50039-7
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
2282-2
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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DSLD |
3522 (Number of products:75)
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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DSLD |
3132 (Number of products:6858)
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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NCI_THESAURUS |
C1444
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admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
14731-4
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
35210-4
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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LOINC |
14733-0
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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WHO-ESSENTIAL MEDICINES LIST |
10.1
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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WHO-ATC |
B03BB01
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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Code System | Code | Type | Description | ||
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62356
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ALTERNATIVE | |||
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2002
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PRIMARY | |||
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1231
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PRIMARY | |||
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C510
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PRIMARY | |||
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6037
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PRIMARY | |||
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CHEMBL1622
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admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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PRIMARY | |||
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FOLIC ACID
Created by
admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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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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admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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PRIMARY | |||
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935E97BOY8
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PRIMARY | |||
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1286005
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PRIMARY | USP-RS | ||
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59-30-3
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PRIMARY | |||
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59-30-3
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PRIMARY | |||
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SUB07774MIG
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PRIMARY | |||
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M5518
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PRIMARY | Merck Index | ||
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4511
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PRIMARY | |||
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D005492
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PRIMARY | |||
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FOLIC ACID
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PRIMARY | |||
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DB00158
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PRIMARY | |||
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68
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)