NAV

(6R)-Folinic acid

Identification

Summary

(6R)-Folinic acid is a drug used to treat and prevent iron and folic acid deficiency.

Generic Name
(6R)-Folinic acid
DrugBank Accession Number
DB03256
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 473.4393
Monoisotopic: 473.165896125
Chemical Formula
C20H23N7O7
Synonyms
  • (6R,2'S)-Folinic acid
  • (6R)-Leucovorin
  • [6R]-5-formyl-5,6,7,8-tetrahydrofolate
  • 6R-Leucovorin
  • Dextrofolinic acid
  • L-Glutamic acid, N-[4-[[[(6R)-2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-
  • N-{[4-({[(6R)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid
External IDs
  • 137643-04-0

Pharmacology

Indication

Not Available

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine hydroxymethyltransferaseNot AvailableGeobacillus kaustophilus (strain HTA426)
UAminomethyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UBifunctional polymyxin resistance protein ArnANot AvailableEscherichia coli (strain K12)
UFormimidoyltransferase-cyclodeaminaseNot AvailableHumans
UN,N-dimethylglycine oxidaseNot AvailableArthrobacter globiformis
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
CapecitabineThe risk or severity of adverse effects can be increased when (6R)-Folinic acid is combined with Capecitabine.
CarbamazepineThe serum concentration of (6R)-Folinic acid can be decreased when it is combined with Carbamazepine.
ColestipolThe serum concentration of (6R)-Folinic acid can be decreased when it is combined with Colestipol.
FlucytosineThe risk or severity of adverse effects can be increased when (6R)-Folinic acid is combined with Flucytosine.
FluorouracilThe risk or severity of adverse effects can be increased when (6R)-Folinic acid is combined with Fluorouracil.
FosphenytoinThe serum concentration of Fosphenytoin can be decreased when it is combined with (6R)-Folinic acid.
GlucarpidaseThe serum concentration of the active metabolites of (6R)-Folinic acid can be reduced when (6R)-Folinic acid is used in combination with Glucarpidase resulting in a loss in efficacy.
Pafolacianine(6R)-Folinic acid may decrease effectiveness of Pafolacianine as a diagnostic agent.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with (6R)-Folinic acid.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with (6R)-Folinic acid.
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Food Interactions
Not Available

Products

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Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Glutamic acid and derivatives
Alternative Parents
N-acyl-alpha amino acids / Hippuric acids / Pterins and derivatives / Aminobenzamides / Phenylalkylamines / Aniline and substituted anilines / Benzoyl derivatives / Secondary alkylarylamines / Hydroxypyrimidines / Dicarboxylic acids and derivatives
show 10 more
Substituents
Amine / Amino acid / Aminobenzamide / Aminobenzoic acid or derivatives / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
73951-54-9
InChI Key
VVIAGPKUTFNRDU-OLZOCXBDSA-N
InChI
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12-,13+/m1/s1
IUPAC Name
(2S)-2-{[4-({[(6R)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILES
[H]N([H])C1=NC(=O)C2=C(N([H])C[C@@H](CN([H])C3=CC=C(C=C3)C(=O)N([H])[C@@H](CCC(O)=O)C(O)=O)N2C=O)N1[H]

References

General References
Not Available
PubChem Compound
135548
PubChem Substance
46506235
ChemSpider
119394
ChEMBL
CHEMBL1232801
ZINC
ZINC000009212428
PDBe Ligand
FON
PDB Entries
1kl2 / 1qd1 / 1vrq / 1xzq / 2bln / 3gee / 3geh / 4lxq / 4lxt / 4lxu …
show 15 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP-3.8Chemaxon
pKa (Strongest Acidic)3.21Chemaxon
pKa (Strongest Basic)4.66Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area215.55 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity126.46 m3·mol-1Chemaxon
Polarizability44.63 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5642
Blood Brain Barrier-0.7779
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7344
P-glycoprotein inhibitor INon-inhibitor0.918
P-glycoprotein inhibitor IINon-inhibitor0.984
Renal organic cation transporterNon-inhibitor0.8708
CYP450 2C9 substrateNon-substrate0.7887
CYP450 2D6 substrateNon-substrate0.814
CYP450 3A4 substrateNon-substrate0.5852
CYP450 1A2 substrateNon-inhibitor0.8748
CYP450 2C9 inhibitorNon-inhibitor0.9123
CYP450 2D6 inhibitorNon-inhibitor0.9326
CYP450 2C19 inhibitorNon-inhibitor0.8984
CYP450 3A4 inhibitorNon-inhibitor0.9475
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9292
Ames testNon AMES toxic0.7955
CarcinogenicityNon-carcinogens0.9361
BiodegradationNot ready biodegradable0.8534
Rat acute toxicity2.4254 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9283
hERG inhibition (predictor II)Non-inhibitor0.5331
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Serine hydroxymethyltransferase
Kind
Protein
Organism
Geobacillus kaustophilus (strain HTA426)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the reversible interconversion of serine and glycine with tetrahydrofolate (THF) serving as the one-carbon carrier. This reaction serves as the major source of one-carbon groups required ...
Gene Name
glyA
Uniprot ID
Q5KUI2
Uniprot Name
Serine hydroxymethyltransferase
Molecular Weight
45175.135 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details2. Aminomethyltransferase
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Transaminase activity
Specific Function
The glycine cleavage system catalyzes the degradation of glycine.
Gene Name
gcvT
Uniprot ID
Q9WY54
Uniprot Name
Aminomethyltransferase
Molecular Weight
40332.235 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details3. Bifunctional polymyxin resistance protein ArnA
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-glucuronate decarboxylase activity
Specific Function
Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto-arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4-amino-4-deoxy-L-a...
Gene Name
arnA
Uniprot ID
P77398
Uniprot Name
Bifunctional polymyxin resistance protein ArnA
Molecular Weight
74288.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details4. Formimidoyltransferase-cyclodeaminase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Microtubule binding
Specific Function
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool.Binds and promotes bundling of vimentin...
Gene Name
FTCD
Uniprot ID
O95954
Uniprot Name
Formimidoyltransferase-cyclodeaminase
Molecular Weight
58925.93 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details5. N,N-dimethylglycine oxidase
Kind
Protein
Organism
Arthrobacter globiformis
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Catalyzes the oxidative demethylation of N,N-dimethylglycine to yield sarcosine, formaldehyde and hydrogen peroxide. The oxidation of dimethylglycine is coupled to the synthesis of 5,10-methylenete...
Gene Name
dmg
Uniprot ID
Q9AGP8
Uniprot Name
Dimethylglycine oxidase
Molecular Weight
89983.935 Da

Drug created at June 13, 2005 13:24 / Updated at June 08, 2021 11:32