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

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
Structure of FOLIC ACID

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

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

-7.1254082E11
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
Folic acid antagonists during pregnancy and the risk of birth defects.
2000 Nov 30
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
A bifunctional dihydrofolate synthetase--folylpolyglutamate synthetase in Plasmodium falciparum identified by functional complementation in yeast and bacteria.
2001 Feb
Cloning, expression, genomic localization, and enzymatic activities of the mouse homolog of prostate-specific membrane antigen/NAALADase/folate hydrolase.
2001 Feb
Determinants of changes in plasma homocysteine in hyperthyroidism and hypothyroidism.
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
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
Supplementation of atherogenic diet with B vitamins does not prevent atherosclerosis or vascular dysfunction in monkeys.
2001 Feb 20
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
Diet and cancer: one view at the start of the millennium.
2001 Jan
Homocysteine: a new cardiac risk factor?
2001 Jan
Gastric tube graft interposition as an oesophageal substitute.
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
Vitamin B12 deficiency in children and adolescents.
2001 Jan
Long-term reduction of plasma homocysteine levels by super-flux dialyzers in hemodialysis patients.
2001 Jan
Rapid communication: L-folinic acid versus folic acid for the treatment of hyperhomocysteinemia in hemodialysis patients.
2001 Jan
Maternal plasma homocysteine levels in women with preterm premature rupture of membranes.
2001 Jan
Diagnosis and treatment of hyperhomocysteinemia.
2001 Jan
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
Factors that influence the penetration of methotrexate through solid tissue.
2001 Jan 1
Impact of the reduced folate carrier on the accumulation of active thiamin metabolites in murine leukemia cells.
2001 Jan 12
Folic acid and miscarriage: an unjustified link.
2001 Jan 15
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
Diet-induced hyperhomocysteinemia exacerbates neointima formation in rat carotid arteries after balloon injury.
2001 Jan 2
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
Synthesis and evaluation of pteroic acid-conjugated nitroheterocyclic phosphoramidates as folate receptor-targeted alkylating agents.
2001 Jan 4
Passive and iontophoretic transdermal penetration of methotrexate.
2001 Jan 5
[Folates, vitamin B12, homocysteine and neural tube defects].
2001 Jan-Feb
Antisense modulation of 5,10-methylenetetrahydrofolate reductase expression produces neural tube defects in mouse embryos.
2001 Jan-Feb
Hyperhomocysteinemia and hypercholesterolemia associated with hypothyroidism in the third US National Health and Nutrition Examination Survey.
2001 Mar
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
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
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

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
FOLIC ACID
DSC   EP   FCC   GREEN BOOK   HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   INCI  
Official Name English
L-GLUTAMIC ACID, N-(4-(((2-AMINO-1,4-DIHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-
Common Name English
VITAMIN M
Common Name English
FOLIAMIN
Brand Name English
N-(4-(((2-AMINO-4-OXO-1,4-DIHYDROPTERIDIN-6-YL)METHYL)AMINO)BENZOYL)-L-GLUTAMIC ACID
Systematic Name English
FOLIC ACID [DSC]
Common Name English
FOLIC ACID [INCI]
Common Name English
FOLDINE
Brand Name English
FOLIC ACID [EP]
Common Name English
INCAFOLIC
Brand Name English
FOLIC ACID [WHO-DD]
Common Name English
FOLVRON COMPONENT FOLIC ACID
Common Name English
NSC-3073
Code English
FOLSAN
Brand Name English
FOLIC ACID [INN]
Common Name English
FOLIC ACID COMPONENT OF FOLVRON
Common Name English
FOLIC ACID [HSDB]
Common Name English
FOLVITE
Brand Name English
FOLETTES
Brand Name English
CALCIUM FOLINATE IMPURITY C [EP]
Common Name English
FOLIC ACID [MART.]
Common Name English
VITAMIN BC
Common Name English
FOLIC ACID [WHO-IP]
Common Name English
FOLIC ACID [JAN]
Common Name English
ACIDUM FOLICUM [WHO-IP LATIN]
Common Name English
FOLIPAC
Brand Name English
FOLACIN
Brand Name English
FOLIC ACID [USP]
Common Name English
N-(P-(((2-AMINO-4-HYDROXY-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-L-GLUTAMIC ACID
Common Name English
FOLIC ACID [MI]
Common Name English
FOLIC ACID [ORANGE BOOK]
Common Name English
FOLATE
Common Name English
FOLIC ACID [USP-RS]
Common Name English
FOLIC ACID [GREEN BOOK]
Common Name English
FOLICET
Brand Name English
B03BB01
Code English
VITAMIN B9
Common Name English
FOLIC ACID [VANDF]
Common Name English
FOLIC ACID [FCC]
Common Name English
MILLAFOL
Brand Name English
PTEROYLGLUTAMIC ACID
Common Name English
Classification Tree Code System Code
WHO-VATC QB03AE01
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 10.1 (FER/FOL)
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
LOINC 2283-0
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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
LIVERTOX 432
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
LOINC 2284-8
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
WHO-ATC B03BB51
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
WHO-ATC B03AE01
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
LOINC 55859-3
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
LOINC 25415-1
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
DSLD 189 (Number of products:374)
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
LOINC 14732-2
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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
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
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
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
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
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
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
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
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
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
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
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
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
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
NCI_THESAURUS C1444
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
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
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
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
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
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
Code System Code Type Description
RXCUI
62356
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
ALTERNATIVE
HSDB
2002
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
DRUG CENTRAL
1231
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
NCI_THESAURUS
C510
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
PUBCHEM
6037
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL1622
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
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
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.
ECHA (EC/EINECS)
200-419-0
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
FDA UNII
935E97BOY8
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
USP_CATALOG
1286005
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY USP-RS
CAS
59-30-3
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
EPA CompTox
59-30-3
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
EVMPD
SUB07774MIG
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
MERCK INDEX
M5518
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY Merck Index
RXCUI
4511
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
MESH
D005492
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
WIKIPEDIA
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
PRIMARY
DRUG BANK
DB00158
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY
INN
68
Created by admin on Sat Jun 26 06:17:45 UTC 2021 , Edited by admin on Sat Jun 26 06:17:45 UTC 2021
PRIMARY