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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H19N7O6
Molecular Weight 441.3975
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Folic acid

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

HIDE SMILES / InChI

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

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
Folic acid-induced acute renal failure in the the rat: morphological studies.
1976 Oct
Failure of periconceptual folic acid to prevent a neural tube defect in the offspring of a mother taking sodium valproate.
1999 Jun
Up-regulation of galectin-3 in acute renal failure of the rat.
2000 Sep
Exocrine pancreatic insufficiency in tropical sprue.
2001
Folate and vitamin B6 from diet and supplements in relation to risk of coronary heart disease among women.
2001
Rationale for risk reduction of cardiovascular disease using homocysteine concentration in blood and plasma as biomarker: support by clinical data.
2001
Folic acid and neural tube defects.
2001
Low seminal plasma folate concentrations are associated with low sperm density and count in male smokers and nonsmokers.
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
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
Homocysteine--a novel risk factor for vascular disease.
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
Oral clefts and vitamin supplementation.
2001 Jan
Effects of folate supplementation on two provisional molecular markers of colon cancer: a prospective, randomized trial.
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
Comparison of the bacterial flora of the duodenum in healthy cats and cats with signs of gastrointestinal tract disease.
2001 Jan 1
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
Synthesis and evaluation of pteroic acid-conjugated nitroheterocyclic phosphoramidates as folate receptor-targeted alkylating agents.
2001 Jan 4
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
Repression of human reduced folate carrier gene expression by wild type p53.
2001 Mar 23
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:34:16 GMT 2023
Edited
by admin
on Fri Dec 15 16:34:16 GMT 2023
Record UNII
935E97BOY8
Record Status Validated (UNII)
Record Version
  • Download
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 [WHO-DD]
Common Name English
INCAFOLIC
Brand Name English
CALCIUM FOLINATE IMPURITY C [EP IMPURITY]
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
FOLIC ACID [MART.]
Common Name English
VITAMIN BC
Common Name English
FOLIC ACID [USP MONOGRAPH]
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
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
FOLIC ACID [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QB03AE01
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
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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LOINC 25415-1
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DSLD 189 (Number of products:374)
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LOINC 14732-2
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LOINC 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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LOINC 49264-5
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LOINC 50039-7
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LOINC 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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LOINC 35210-4
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LOINC 14733-0
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WHO-ESSENTIAL MEDICINES LIST 10.1
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
WHO-ATC B03BB01
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
Code System Code Type Description
RXCUI
62356
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
ALTERNATIVE
DAILYMED
935E97BOY8
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
HSDB
2002
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
DRUG CENTRAL
1231
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
NSC
3073
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
NCI_THESAURUS
C510
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
PUBCHEM
6037
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL1622
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
CHEBI
176842
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
FOLIC ACID
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
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 Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
FDA UNII
935E97BOY8
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
CAS
59-30-3
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PRIMARY
EPA CompTox
DTXSID0022519
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PRIMARY
EVMPD
SUB07774MIG
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PRIMARY
CHEBI
62501
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
RS_ITEM_NUM
1286005
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PRIMARY
CHEBI
67011
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PRIMARY
MERCK INDEX
m5518
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PRIMARY Merck Index
SMS_ID
100000085634
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
RXCUI
4511
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
CHEBI
37445
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
MESH
D005492
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PRIMARY
CHEBI
27470
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
WIKIPEDIA
FOLIC ACID
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
DRUG BANK
DB00158
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
INN
68
Created by admin on Fri Dec 15 16:34:16 GMT 2023 , Edited by admin on Fri Dec 15 16:34:16 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Nutritional value per 100 g (3.5 oz) - 63 ug (16%)
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