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Folinic acid

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CAS:58-05-9
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Related articles

  • What is Folinic acid?
  • Folinic acid is used to prevent severe toxic effects caused by methotrexate overdose or high-dose treatment.
  • Aug 5,2021
Folinic acid Basic information
Description Uses Characteristics Pharmacology Preparation
Product Name:Folinic acid
Synonyms:5-formyl-5,6,7,8-tetrahydropteroyl-l-glutamicacid;leucoverin;5-formyl-5,6,7,8-tetrahydrofolate;N5-formyl-5,6,7,8-tetrahydrofolate;N5-formyl-tetrahydrofolate;2-[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]aminopentanedioic acid;(6R,S)-5-Formyltetrahydrofolate;5-Formyl-5,6,7,8-tetrahydrofolic acid
CAS:58-05-9
MF:C20H23N7O7
MW:473.44
EINECS:200-361-6
Product Categories:Pharmaceutical Raw Materials
Mol File:58-05-9.mol
Folinic acid Structure
Folinic acid Chemical Properties
Melting point 245°C (rough estimate)
Boiling point 573.92°C (rough estimate)
alpha D20 +14.26° (c = 3.42 as anhydr Ca salt)
density 1.4485 (rough estimate)
refractive index 1.6800 (estimate)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
solubility DMSO:172.5(Max Conc. mg/mL);364.35(Max Conc. mM)
pka3.1, 4.8, 10.4(at 25℃)
form Solid
color Pale Yellow to Light Yellow
Water Solubility >1350g/L(25 ºC)
Stability:Hygroscopic
CAS DataBase Reference58-05-9(CAS DataBase Reference)
Safety Information
Hazardous Substances Data58-05-9(Hazardous Substances Data)
Folinic acid Usage And Synthesis
DescriptionFolinic acid, chemical name N-[4-[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridyl) Methyl]amino]benzoyl-L-glutamic acid has been widely used in cancer combined chemotherapy. Folinic acid enters the human body through the ingestion and absorption pathway of folate. Folinic acid (calcium folinate) is a special form of reduced folic acid (folate).
Uses1. It is mainly used as an antidote for folic acid antagonists (such as methotrexate, pyrimethamine or trimethoprim, etc.).2. It is used to prevent severe toxic effects caused by methotrexate overdose or high-dose treatment.3. Megaloblastic anemia caused by folic acid deficiency.4. When combined with fluorouracil, it is used to treat advanced colon cancer and rectal cancer. 
CharacteristicsL-leucovorin is used as an anti-tumor antidote and anti-megaloblastic anemia adjuvant. Its dosage is 1/2 of folinic acid. L-leucovorin does not need to be reduced by dihydrofolate reductase to participate in the use of folate as a The reaction is derived from carbon units, and L-leucovorin can actively or passively pass through the cell membrane; the basic function of L-leucovorin is the same as folic acid, but the effect is better than folic acid. At the same time, L-leucovorin also has the effect of stimulating the growth and maturation of white blood cells, which can improve the growth and maturation of white blood cells. 
PharmacologyFolic acid (pteroylglutamic acid), an essential water-soluble vitamin, consists of a pteridine ring joined to PABA (para-aminobenzoic acid) and glutamic acid.3 Folic acid is the most common of the many folate congeners that exist in nature and are essential for normal cellular metabolic functions. Folic acid is rarely called vitamin B9. After absorption, folic acid is reduced by dihydrofolic acid reductase (DHFR) to dihydrofolic acid and then tetrahydrofolic acid (THF), which accepts one-carbon groups. Tetrahydrofolic acid serves as the precursor for several biologically active forms of folic acid, including 5-formyltetrahydrofolic acid (5-formyl THF), which is best known as folinic acid, leucovorin, and citrovorum factor. 
PreparationIn a 1L reaction flask, first add 0.45L of pure water, heat to 55-60℃ with stirring, then add 15g (0.0245mol, water 16.4%) of levofolinate, keep it at 55-60℃, and stir to It is almost dissolved, and the temperature is lowered to 0-10°C first, and an aqueous sodium carbonate solution (2.6g sodium carbonate (0.0245mol) dissolved in 45mL of pure water) is added dropwise, keeping the temperature at 0-10°C, after dripping, keep warm and stir for 1 hour. The precipitated solid is filtered out, the filter cake is washed once with 20 ml of pure water, and the filtrate is the sodium levofolinate solution. Put the filtrate into a 1L reaction flask, stir and lower the temperature to 0-5°C, control the temperature of the reaction system at 0-5°C, and add 1N dilute hydrochloric acid uniformly. When the pH of the acidification end point is 2.0-2.5, stop the dripping. Stir for about 30 minutes, then stand and age for 30 minutes, filter, and wash the filter cake twice with 75 mL of pure water. The wet product is freeze-dried to obtain 9.1 g of Folinic acid. Yield: 78%
Chemical PropertiesCrystals. Sparingly soluble in water.
OriginatorLeucovorin calcium,AstraZeneca
UsesAnti-anemic (folate deficiency); antidote (to folic acid antagonists).
UsesFolinic Acid is used in combination with 5-fluorouracil in the treatment of colorectal cancers. It also functions as a useful antidotal therapy medication for decreasing the toxic effect of methotrexate overdosing.
DefinitionChEBI: A formyltetrahydrofolic acid in which the formyl group is located at position 5.
Manufacturing Process5,10-Methenyl-5,6,7,8-tetrahydrofolic acid, chloride hydrochloride dihydrate (20 g) was added in one portion to 100 ml water at 60°C followed by N,Ndiethylethanolamine (14.9 g) which adjusted the pH to 6. The mixture was maintained at reflux for 5 hours and the pH kept between 5.7 and 6.2 by addition of N,N-diethylethanolamine. The mixture was cooled, synthetic magnesium silicate (15 g) added and slurried, and filtered through celite and diluted with 40 ml SD3A (95% ethanol with 5% methanol). The filtrate was kept at -5°C for 16 hours, aqueous calcium chloride (4.0 g) was added dropwise to the cold filtrate, and the precipitate filtered, washed with SD3A (100 ml) and with ethyl acetate (100 ml) and dried under reduced pressure.
Brand nameWellcovorin (GlaxoSmithKline).
Therapeutic FunctionAntidote (folic acid antagonists), Antianemic
Folinic acid Preparation Products And Raw materials
Raw materialsFOROXYMITHINE-->Diethylaminoethanol
Tag:Folinic acid(58-05-9) Related Product Information
Citric acid Folic acid 6-Aminocaproic acid Benzoyl peroxide Nadph tetrasodium salt Carbachol L-Tetrahydrofolic Acid ALTRENOGEST Hyaluronic acid Tris(hydroxymethyl)aminomethane Ethyl 2-(Chlorosulfonyl)acetate Glycine 3-Aminophenol 5,10-Methenyltetrahydrofolic acid Ascoric Acid 2-Amino-7-(chloromethyl)pteridin-4(1H)-one Levomefolate calcium 6-hydroxymethylpterin