U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N7O6.Na.H
Molecular Weight 463.3793
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOLATE SODIUM

SMILES

[H+].[Na+].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=ZTYOEHTVHXWFJT-YDALLXLXSA-M
InChI=1S/C19H19N7O6.Na/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);/q;+1/p-1/t12-;/m0./s1

HIDE SMILES / InChI

Description
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®.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FOLVITE

Approved Use

Indications 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

1947
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
25.4 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
76 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.93 h
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

Doses

DosePopulationAdverse 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...
Other AEs:
Autism spectrum disorder (6.8%)
Sources:
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

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Harmful effect of megadoses of vitamins: electroencephalogram abnormalities and seizures induced by intravenous folate in drug-treated epileptics.
1975 Jan
A bifunctional dihydrofolate synthetase--folylpolyglutamate synthetase in Plasmodium falciparum identified by functional complementation in yeast and bacteria.
2001 Feb
Hypercoagulable thrombophilic defects and hyperhomocysteinemia in patients with recurrent pregnancy loss.
2001 Feb
Low seminal plasma folate concentrations are associated with low sperm density and count in male smokers and nonsmokers.
2001 Feb
Analysis of uracil DNA glycosylase in human colorectal cancer.
2001 Feb
Intake of vegetables rich in carotenoids and risk of coronary heart disease in men: The Physicians' Health Study.
2001 Feb
Lowered weight gain during pregnancy and risk of neural tube defects among offspring.
2001 Feb
Folate reception by vegetative Dictyostelium discoideum amoebae: distribution of receptors and trafficking of ligand.
2001 Feb
Homocysteine, its metabolites, and B-group vitamins in renal transplant patients.
2001 Feb
Is there a role of cyclosporine A on total homocysteine export from human renal proximal tubular epithelial cells?
2001 Feb
Effect of MTHFR genotypes and hyperhomocysteinemia on patient and graft survival in kidney transplant recipients.
2001 Feb
Treatment of hyperhomocysteinemia in hemodialysis patients and renal transplant recipients.
2001 Feb
Recent insights into the molecular genetics of the homocysteine metabolism.
2001 Feb
Homocysteine metabolism in renal failure.
2001 Feb
The folate cycle and disease in humans.
2001 Feb
Changes in markers of anemia and iron metabolism and how they are influenced by antianemics in postpartum period.
2001 Feb
Methylenetetrahydrofolate reductase genotypes and predisposition to atherothrombotic disease; evidence that all three MTHFR C677T genotypes confer different levels of risk.
2001 Feb
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
Selected food intake and risk of multiple pregnancies.
2001 Feb
Homocysteine and coronary heart disease in the Caerphilly cohort: a 10 year follow up.
2001 Feb
C677T variant form at the MTHFR gene and CL/P: a risk factor for mothers?
2001 Feb 1
It's just a vitamin..
2001 Feb 1
Lack of clinical utility of folate levels in the evaluation of macrocytosis or anemia.
2001 Feb 1
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
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
Phase I dose-escalation and pharmacokinetic study of a novel folate analogue AG2034.
2001 Feb 2
[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options].
2001 Jan
Homocysteine--a novel risk factor for vascular disease.
2001 Jan
SLATE: a method for the superposition of flexible ligands.
2001 Jan
Preconceptual folic acid: opportunity for preconceptual counseling offers opportunity to help prevent neural tube defects.
2001 Jan
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
Gene-environment and gene-gene interaction in the determination of plasma homocysteine levels in healthy middle-aged men.
2001 Jan
Relationships between homocysteine, folate and vitamin B12 levels with the methylenetetrahydrofolate reductase polymorphism, in Indians from Western Venezuela.
2001 Jan
[Theoretical construction of chemotherapeutic tactics for advanced or recurrent gastrointestinal carcinoma].
2001 Jan
Characterization of three genes encoding enzymes of the folate biosynthetic pathway in Plasmodium falciparum.
2001 Jan
Effects of folate supplementation on two provisional molecular markers of colon cancer: a prospective, randomized trial.
2001 Jan
Nitrous oxide-induced cobalamin deficiency.
2001 Jan
Ascertainment of pregnancies terminated because of birth defects: effect on completeness of adding a new source of data.
2001 Jan
Gastric tube graft interposition as an oesophageal substitute.
2001 Jan
Nutritional status of folate and colon cancer risk: evidence from NHANES I epidemiologic follow-up study.
2001 Jan
Lp(a) lipoprotein--an independent risk factor for coronary heart disease after menopause.
2001 Jan
Antimicrobial activities of dihydrofolate reductase inhibitors, used singly or in combination with dapsone, against Mycobacterium ulcerans.
2001 Jan
Retroviral expression of Escherichia coli thymidylate synthase cDNA confers high-level antifolate resistance to hematopoietic cells.
2001 Jan 1
Folic acid and miscarriage: an unjustified link.
2001 Jan 15
Physical activity and risk for cardiovascular events in diabetic women.
2001 Jan 16
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
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
Subnormal concentrations of serum cobalamin (vitamin B12) in cats with gastrointestinal disease.
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

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
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.
Name Type Language
FOLATE SODIUM
WHO-DD  
Common Name English
SODIUM FOLATE
Common Name English
L-GLUTAMIC ACID, N-(4-(((2-AMINO-1,4-DIHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-, SODIUM
Common Name English
SODIUM PTEROYLGLUTAMATE
Common Name English
L-GLUTAMIC ACID, N-(4-(((2-AMINO-1,4-DIHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-, MONOSODIUM SALT
Common Name English
FOLIC ACID, MONOSODIUM SALT
Common Name English
FOLIC ACID SODIUM SALT [MI]
Common Name English
Folate sodium [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
229-348-3
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
DAILYMED
9P9W8GGU78
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
NCI_THESAURUS
C76079
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
RXCUI
1300473
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m5518
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY Merck Index
CAS
60672-17-5
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
NON-SPECIFIC STOICHIOMETRY
EPA CompTox
DTXSID50983430
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
SMS_ID
100000086997
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
CONCEPT Dietary Supplement
DRUG BANK
DBSALT001918
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
PUBCHEM
135565736
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
EVMPD
SUB02246MIG
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
FDA UNII
9P9W8GGU78
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY
CAS
6484-89-5
Created by admin on Fri Dec 15 15:48:08 GMT 2023 , Edited by admin on Fri Dec 15 15:48:08 GMT 2023
PRIMARY