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
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 |
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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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Dietary intake of vitamins, minerals, and fiber of persons ages 2 months and over in the United States: Third National Health and Nutrition Examination Survey, Phase 1, 1988-91. | 1994 Nov 14 |
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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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Folate and vitamin B6 from diet and supplements in relation to risk of coronary heart disease among women. | 2001 |
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Evidence of folic acid and folate in the prevention of neural tube defects. | 2001 |
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Homocysteine and stroke. | 2001 Feb |
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The alpha folate receptor is highly activated in malignant pleural mesothelioma. | 2001 Feb |
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Vitamin Intervention for Stroke Prevention (VISP) trial: rationale and design. | 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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The folate cycle and disease in humans. | 2001 Feb |
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Phase I dose-escalation and pharmacokinetic study of a novel folate analogue AG2034. | 2001 Feb 2 |
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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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Nitrous oxide-induced cobalamin deficiency. | 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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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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Multivitamins, folate, and colon cancer. | 2001 Jan |
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Physical activity and risk for cardiovascular events in diabetic women. | 2001 Jan 16 |
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[Folates, vitamin B12, homocysteine and neural tube defects]. | 2001 Jan-Feb |
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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21 CFR 172.345
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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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100000085634
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FOLIC ACID
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DB00158
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)