CAS 58-05-9|Folinic acid

Introduction：Basic information about CAS 58-05-9|Folinic acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Folinic acid BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

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

Names

Name	5-formyltetrahydrofolic acid
Synonym	More Synonyms

Folinic acid BiologicalActivity

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	Signaling Pathways >>Cell Cycle/DNA Damage >>AntifolateResearch Areas >>Cancer
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.

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

Signaling Pathways >>Cell Cycle/DNA Damage >>AntifolateResearch Areas >>Cancer

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℃

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

Recommended......