Folinic acid

Modify Date: 2025-08-28 08:00:17

Folinic acid Structure
Folinic acid structure
Common Name Folinic acid
CAS Number 58-05-9 Molecular Weight 473.43900
Density 1.68g/cm3 Boiling Point N/A
Molecular Formula C20H23N7O7 Melting Point 245ºC (decomp)
MSDS N/A Flash Point N/A

 Use of Folinic acid


Folinic acid is an adjuvant used in cancer chemotherapy involving the drug methotrexate.Target: AntifolateFolinic acid is a 5-formyl derivative of tetrahydrofolic acid. It is readily converted to other reduced folic acid derivatives (e.g., tetrahydrofolate), and, thus, has vitamin activity that is equivalent to that of folic acid. Since it does not require the action of dihydrofolate reductase for its conversion, its function as a vitamin is unaffected by inhibition of this enzyme by drugs such as methotrexate. In 1980s, however, folinic acid was found to reactivate the dihydrofolate reductase itself even when methotrexate exists. Although the mechanism is not very clear, the polyglutamylation of methotrexate and dihydrofolate in malignant cells is considered to play an important role in the selective reactivation of dihydrofolate reductase by folinic acid in normal cells [1]. Folinic acid is generally administered along with MTX as a rescue agent to decrease MTX-induced toxicity. However, information regarding the inhibitory effect of folinic acid against cytogenetic damage caused by MTX is limited. This study was conducted to assess the cytogenetic effect of MTX and its inhibition by folinic acid (FA) using the micronucleus and chromosomal aberration assays concurrently [2].

 Names

Name 5-formyltetrahydrofolic acid
Synonym More Synonyms

 Folinic acid Biological Activity

Description Folinic acid is an adjuvant used in cancer chemotherapy involving the drug methotrexate.Target: AntifolateFolinic acid is a 5-formyl derivative of tetrahydrofolic acid. It is readily converted to other reduced folic acid derivatives (e.g., tetrahydrofolate), and, thus, has vitamin activity that is equivalent to that of folic acid. Since it does not require the action of dihydrofolate reductase for its conversion, its function as a vitamin is unaffected by inhibition of this enzyme by drugs such as methotrexate. In 1980s, however, folinic acid was found to reactivate the dihydrofolate reductase itself even when methotrexate exists. Although the mechanism is not very clear, the polyglutamylation of methotrexate and dihydrofolate in malignant cells is considered to play an important role in the selective reactivation of dihydrofolate reductase by folinic acid in normal cells [1]. Folinic acid is generally administered along with MTX as a rescue agent to decrease MTX-induced toxicity. However, information regarding the inhibitory effect of folinic acid against cytogenetic damage caused by MTX is limited. This study was conducted to assess the cytogenetic effect of MTX and its inhibition by folinic acid (FA) using the micronucleus and chromosomal aberration assays concurrently [2].
Related Catalog
References

[1]. Goldman, I.D. and L.H. Matherly, Biochemical factors in the selectivity of leucovorin rescue: selective inhibition of leucovorin reactivation of dihydrofolate reductase and leucovorin utilization in purine and pyrimidine biosynthesis by methotrexate and dihydrofolate polyglutamates. NCI Monogr, 1987(5): p. 17-26.

[2]. Keshava, C., et al., Inhibition of methotrexate-induced chromosomal damage by folinic acid in V79 cells. Mutat Res, 1998. 397(2): p. 221-8.

 Chemical & Physical Properties

Density 1.68g/cm3
Melting Point 245ºC (decomp)
Molecular Formula C20H23N7O7
Molecular Weight 473.43900
Exact Mass 473.16600
PSA 219.84000
LogP 1.15290
Index of Refraction 1.748
InChIKey VVIAGPKUTFNRDU-ABLWVSNPSA-N
SMILES Nc1nc2c(c(=O)[nH]1)N(C=O)C(CNc1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1)CN2
Storage condition 2-8℃

 Synthetic Route

~%

Folinic acid Structure

Folinic acid

CAS#:58-05-9

Literature: CERBIOS-PHARMA S.A. Patent: WO2005/80395 A2, 2005 ; Location in patent: Page/Page column 4-5 ;

 Precursor & DownStream

Precursor  1

DownStream  1

 Folinic acidBioassay

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Name: DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole)
Source: ChEMBL
Target: Delta-type opioid receptor
External Id: CHEMBL1909180
Name: DRUGMATRIX: Nitric Oxide Synthase, Inducible (iNOS) enzyme inhibition (substrate: L-A...
Source: ChEMBL
Target: Nitric oxide synthase, inducible
External Id: CHEMBL1909179
Name: Number of mice infected to tat of total number of mice (11/11)
Source: ChEMBL
Target: Mus musculus
External Id: CHEMBL744870
Name: DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine)
Source: ChEMBL
Target: Mu-type opioid receptor
External Id: CHEMBL1909182
Name: DRUGMATRIX: Opiate kappa (OP2, KOP) radioligand binding (ligand: [3H] Diprenorphine)
Source: ChEMBL
Target: Kappa-type opioid receptor
External Id: CHEMBL1909181
Name: DRUGMATRIX: Phosphodiesterase PDE3 enzyme inhibition (substrate: [3H]cAMP + cAMP)
Source: ChEMBL
Target: N/A
External Id: CHEMBL1909184
Name: DRUGMATRIX: Phorbol Ester radioligand binding (ligand: [3H] PDBu)
Source: ChEMBL
Target: N/A
External Id: CHEMBL1909183
Name: DRUGMATRIX: Phosphodiesterase PDE5 enzyme inhibition (substrate: [3H]cGMP + cGMP)
Source: ChEMBL
Target: cGMP-specific 3',5'-cyclic phosphodiesterase
External Id: CHEMBL1909186
Name: DRUGMATRIX: Phosphodiesterase PDE4 enzyme inhibition (substrate: [3H]cAMP + cAMP)
Source: ChEMBL
Target: N/A
External Id: CHEMBL1909185
Name: DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)
Source: ChEMBL
Target: Muscarinic acetylcholine receptor M3
External Id: CHEMBL1909172
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 Synonyms

5-formyl tetrahydrofolate
Folinic acid
MFCD00867488
sodium salt of 4-amino-4-deoxypteroic acid
4-Amino-4-deoxypteroic acid
EINECS 200-361-6
folic acid sodium salt
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