58-05-9 Usage
Description
Folinic 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).
Uses
Different sources of media describe the Uses of 58-05-9 differently. You can refer to the following data:
1. 1. 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.
2. Folinic 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.
Characteristics
L-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.
Pharmacology
Folic 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.
Preparation
In 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 Properties
Crystals. Sparingly soluble in water.
Definition
ChEBI: A formyltetrahydrofolic acid in which the formyl group is located at position 5.
Check Digit Verification of cas no
The CAS Registry Mumber 58-05-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 58-05:
(4*5)+(3*8)+(2*0)+(1*5)=49
49 % 10 = 9
So 58-05-9 is a valid CAS Registry Number.
InChI:InChI=1/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-/m0/s1
58-05-9Relevant articles and documents
Synthesis and physicochemical characterization of (6: S)-5-formiminotetrahydrofolate; A reference standard for metabolomics
Lewin,Silinski,Zhong,Gilbert,Mascarella,Seltzman
, p. 5684 - 5690 (2018/08/17)
The one-carbon carrier of the formate oxidation level derived from the interaction of tetrahydrofolate and formiminoglutamate, which has been tentatively identified as 5-formiminoltetrahydrofolate, has been prepared by chemical synthesis. Treatment of a solution of (6S)-tetrahydrofolate in aqueous base with excess ethyl formimidate in the presence of anti-oxidant under anaerobic conditions afforded a gummy solid which, based on mass spectral analysis, conformed to a monoformimino derivative of tetrahydrofolate. Further physicochemical characterization by validated methods strongly suggested that the product of chemical synthesis was identical to the enzymatically produced material and that it was, in fact, (6S)-5-formiminotetrahydrofolate. Conditions and handling methods toward maintaining the integrity of this highly sensitive compound were identified and are described, as is analytical methodology, useful for research studies using it.
Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same
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, (2010/05/13)
Monoclonal antibodies that bind specifically to Claudin 3 expressed on cell surface are provided. The antibodies of the present invention are useful for diagnosis of cancers that have enhanced expression of Claudin 3, such as ovarian cancer, prostate cancer, breast cancer, uterine cancer, liver cancer, lung cancer, pancreatic cancer, stomach cancer, bladder cancer, and colon cancer. The present invention provides monoclonal antibodies showing cytotoxic effects against cells of these cancers. Methods for inducing cell injury in Claudin 3-expressing cells and methods for suppressing proliferation of Claudin 3-expressing cells by contacting Claudin 3-expressing cells with a Claudin 3-binding antibody are disclosed. The present application also discloses methods for diagnosis or treatment of cancers.
Enantioselective catalyses CXXXV [1]. Stereoselective hydrogenation of folic acid and 2-methylquinoxaline with optically active rhodium(I)-phosphane complexes
Brunner, Henri,Rosenboem, Sabine
, p. 1371 - 1382 (2007/10/03)
In the hydrogenation of the C=N double bonds of the pyrazine ring of folic acid to 5,6,7,8-tetrahydrofolic acid a new asymmetric center is formed at C6 of the pteridine system. With rhodium(I) catalysts made from optically active phosphanes, which are immobilized on silical gel, the hydrogenation in aqueous solution can be controlled stereoselectively. The highest diastereomeric excess of ca. 40% is obtained with (-)-BPPM containing catalysts. The hydrogenation of the biomolecule folic acid in aqueous solution is also possible homogeneously with rhodium(I)-phosphane catalysts, the ligands of which contain sulfonic acid groups and polyether fragments. The homogeneous hydrogenations proceed slower and with somewhat reduced diastereoselectivities compared to the heterogeneous catalyses. The hydrogenation of 2-methylquinoxaline is a model system for the reduction of folic acid. The usual rhodium(I)-phosphane catalysts afford only small enantioselectivities.
