151533-22-1 Usage
Description
Levomefolate calcium, also known as calcium L-5-methyltetrahydrofolate (L-5-MTHF-Ca), is a synthetic derivative of folic acid and belongs to the group of folate vitamins (Vitamin B9, Folacin). It is a coenzymated form of folic acid and a more bioavailable alternative in dietary supplements. Levomefolate calcium is a stable salt of the naturally occurring form of folates and is the predominant folate form in foods. It is the calcium salt of 5-methyltetrahydrofolic acid, a biologically active form of folic acid that functions, in conjunction with Vitamin B12, as a methyl-group donor involved in the conversion of homocysteine to methionine. The availability of methyl groups is essential for a variety of methylation reactions, including the synthesis of DNA and proper neural tube closure. Levomefolate calcium is an off-white to pale yellow solid.
Uses
1. Used in Pharmaceutical Industry:
Levomefolate calcium is used as an antidote for folic acid antagonists (such as methotrexate, pyrimethamine, benzyl cefalexin, and trimethoprim) for the prevention of severe toxic effects caused by methotrexate dose or overdose treatment.
2. Used in Nutritional Supplements:
Levomefolate calcium is used as a supplement for the treatment of diseases such as inflammatory diarrhea and protein-energy malnutrition (poor nutrition), as well as pregnancy or infancy megaloblastic anemia caused by poor folic acid levels.
3. Used in Oncology:
Levomefolate calcium is used as adjuvant therapy for colon cancer and rectal cancer. It is also used in combination with 5-FU for the treatment of digestive tract tumors or other 5-FU-sensitive tumors. High-dose levomefolate calcium, used in conjunction with 5-FU, is a fundamental part of the current treatment for colon and rectal cancer.
4. Used in Pediatric Oncology:
Levomefolate calcium is used for children with leukemia, lymphoma, and osteosarcoma, particularly during high-dose MTX treatment when a rescue is needed.
5. Used in Contraceptive Formulations:
Levomefolate calcium is included in formulations of certain oral contraceptives to ensure adequate folic acid levels in women of child-bearing age, reducing the risk of neural tube defects.
6. Used in the Treatment of Major Depressive Disorder, Cardiovascular Disease, and Cancer:
Levomefolate calcium can be used for the treatment of these conditions due to its involvement in many important in vivo processes, including DNA reproduction, the cysteine cycle, and the regulation of homocysteine.
7. Used in the Treatment of Hyperhomocysteinemia:
Levomefolate calcium can be used for the treatment of hyperhomocysteinemia regularly found in hemodialysis patients, as it is the form of folate found in circulation and transported across membranes into tissues and across the blood-brain barrier.
Function
Folic acid from Levomefolate calcium(Calcium L-5-Methyltetrahydrofolate) will reduce the ability of cells to synthesize and repair DNA. Supplementing folic acid may be a more advantageous way to increase folic acid to reduce homocysteine levels, and support normal cell proliferation, vascular endothelial function. Cardiovascular disease, nervous system function, Especially supplementing 5-MTHF(Calcium L-5-Methyltetrahydrofolate) during pregnancy has been shown to reduce the risk of neural tube malformations and recurrence.
Metabolic pathways
Ordinary folic acid must be converted to L- methylfolate to participate in the two main metabolic pathways: methylation process and DNA synthesis. The only form of free folic acid that usually appears in human plasma and cells is 5-mthf. Lack of folic acid is usually due to lack of vitamins, which leads to insufficient intake. During pregnancy, breastfeeding, and children's growth, the need for folic acid is increased.
Mechanism of Action
The? biochemical pathways of folic acid involves a series of enzymatic reactions and cofactors. The absorbed folic acid is reduced and methylated to 5-MTHF(Calcium L-5-Methyltetrahydrofolate) during the metabolism of intestinal mucosal cells. This transformation is limited and does not change the appearance of folic acid in the blood circulation. The heavy amino acid is then converted to s-adenosylmethionine (SAMe), and the methyl donor is involved in a number of biochemical processes. It can also be used as a donor to participate in the synthesis of nucleotides and support biosynthesis of DNA.
Pharmacokinetics
Absorption: Orally administered levomefolate calcium is absorbed rapidly and is incorporated into the body folate pool. Peak plasma concentrations of about 50 nmol/l above baseline are reached within 0,5 to 1,5 hours after single oral administration of 0,451 mg levomefolate calcium.Distribution: Biphasic kinetics is reported for folates with a fast- and a slow-turnover pool. The fast-turnover pool probably reflecting newly absorbed folate is consistent with the terminal half-life of approximately 4 to 5 hours after single oral administration of 0,451 mg levomefolate calcium. The slow-turnover pool reflecting turnover of folate polyglutamate has a mean residence time of greater than or equal to 100 days. Exogenous folate and an enterohepatic folate cycle help to maintain a constant supply of L-5-methyl-THF. Elimination: L-5-methyl-THF is eliminated from the body by urinary excretion of intact folates and catabolic products as well as faecal excretion through a biphasic kinetics process. A rapid decline in urinary and faecal concentration of folates and their catabolites with a half-life of several hours is followed by a long decline with a half-life of about 100 to 360 days. Steady-state conditions: Steady-state conditions for L-5-methyl-THF in plasma after intake of 0,451 mg levomefolate calcium are reached after about 8 to 16 weeks depending on the baseline levels. In red blood cells achievement of steady-state is delayed due to the long life-span of red blood cells of about 120 days.https://www.bayer.com/sites/default/files/YASMIN_PLUS_EN_PI.pdf
Folic Acid Supplement
Folic acid is the man-made form of folate. Folate is a B-vitamin naturally found in some foods. It is needed to form healthy cells, especially red blood cells. Folic acid supplements may come in different forms (such as L-methylfolate, levomefolate, methyltetrahydrofolate). They are used to treat or prevent low folate levels. Low folate levels can lead to certain types of anemia. Conditions that can cause low folate levels include poor diet, pregnancy, alcoholism, liver disease, certain stomach/intestinal problems, kidney dialysis, among others. Women of childbearing age should receive adequate amounts of folic acid either through their diet or supplements to prevent infant spinal cord birth defects. The calcium salt of Levomefolate calcium which belongs to the group of folate vitamins (Vitamin B9, Folacin). It is a coenzymated form of folic acid and a more bioavailable alternative in dietary supplements.
Biological Functions
L-5-Methyltetrahydrofolate calcium is the calcium salt of L-5-methyltetrahydrofolic acid, and a member of the folate group of vitamins (Vitamin B9). It is the coenzymated and most active form of folic acid, which performs many vital cellular functions, including DNA reproduction, cysteine cycle and homocysteine regulation. L-5-Methyltetrahydrofolate calcium is used as in dietary supplements and has been proposed for treatment of cardiovascular disease.
Clinical Use
Folates are a class of water soluble compounds belonging to the Vitamin B complex which are essential for a number of metabolic functions, including processes involved in the development and metabolism of CNS and the production of DNA and RNA, primarily in infancy, adolescence and pregnancy.Calcium Levomefolate is the active metabolic form of folates in the body.Folate deficiency consequences can be as serious as birth defects (i.e. "spina bifida"), megaloblastic anaemia, and some types of depression.Calcium Levomefolate can be the most effective treatment to remedy those deficiencies.Calcium Levomefolate is formulated in many medical supplements for cases of folate deficiency or need for increased uptake; it is prescribed during pregnancy to prevent birth defects associated with CNS formation and functionality.It is also the active ingredient in medicinal products prescribed for certain types of depression, disturbed behaviour and Mild Cognitive Impairment (MCI)
Check Digit Verification of cas no
The CAS Registry Mumber 151533-22-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,1,5,3 and 3 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 151533-22:
(8*1)+(7*5)+(6*1)+(5*5)+(4*3)+(3*3)+(2*2)+(1*2)=101
101 % 10 = 1
So 151533-22-1 is a valid CAS Registry Number.
InChI:InChI=1/C20H25N7O6.Ca/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29;/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31);/q;+2/p-2/t12-,13-;/m0./s1
