Synonym
Levomefolate magnesium; L-Methylfolate magnesium;
IUPAC/Chemical Name
monomagnesium mono((S)-2-(4-((((S)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzamido)-4-carboxybutanoate)
InChi Key
UNKHRTFYDNBUHK-QNTKWALQSA-M
InChi Code
InChI=1S/C20H25N7O6.Mg/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-1/t12-,13-;/m0./s1
SMILES Code
O=C(O)CC[C@@H](C([O-])=O)NC(C1=CC=C(NC[C@@H]2N(C)C3=C(N=C(N)NC3=O)NC2)C=C1)=O.[Mg+2]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Levomefolate magnesium is the magnesium salt of the metabolite of folic acid (Vitamin B9) and it is a predominant active form of folate found in foods and in the blood circulation, accounting for 98% of folates in human plasma.
In vitro activity:
In addition, FA (folic acid) could ameliorate inflammation and decrease ROS production induced by Hcy. Furthermore, FA pre-treatment suppress palmitate -induced (NF-κB) p65 level in palmitate or Hcy stimulated cells.
Reference: Arch Physiol Biochem. 2021 Feb 17:1-8. https://pubmed.ncbi.nlm.nih.gov/33596128/
In vivo activity:
FA (folic acid) significantly reduced the expression levels of nuclear factor-κ-gene binding (NF-κB) p65/Rela and interleukin-6 (IL-6) in rat arterial tissues, as well as the levels of plasma HHcy and serum malondialdehyde (MDA) in hypertension associated with HHcy rats (p < 0.05).
Reference: Vascular. 2021 Aug 6:17085381211036549. https://pubmed.ncbi.nlm.nih.gov/34362270/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
482.76
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Bagherieh M, Kheirollahi A, Zamani-Garmsiri F, Emamgholipour S, Meshkani R. Folic acid ameliorates palmitate-induced inflammation through decreasing homocysteine and inhibiting NF-κB pathway in HepG2 cells. Arch Physiol Biochem. 2021 Feb 17:1-8. doi: 10.1080/13813455.2021.1878539. Epub ahead of print. PMID: 33596128.
2. Yang H, Qin D, Xu S, He C, Sun J, Hua J, Peng S. Folic acid promotes proliferation and differentiation of porcine pancreatic stem cells into insulin-secreting cells through canonical Wnt and ERK signaling pathway. J Steroid Biochem Mol Biol. 2021 Jan;205:105772. doi: 10.1016/j.jsbmb.2020.105772. Epub 2020 Oct 19. PMID: 33091596.
3. Zhang L, Li Z, Xing C, Ma X, Xu R. The protective mechanism of folic acid on hyperhomocysteinemia-related arterial injury in spontaneously hypertensive rats: Folic acid against arterial inflammation. Vascular. 2021 Aug 6:17085381211036549. doi: 10.1177/17085381211036549. Epub ahead of print. PMID: 34362270.
4. Budni J, Moretti M, Freitas AE, Neis VB, Ribeiro CM, de Oliveira Balen G, Rieger DK, Leal RB, Rodrigues ALS. Behavioral and neurochemical effects of folic acid in a mouse model of depression induced by TNF-α. Behav Brain Res. 2021 Aug 3;414:113512. doi: 10.1016/j.bbr.2021.113512. Epub ahead of print. PMID: 34358572.
In vitro protocol:
1. Bagherieh M, Kheirollahi A, Zamani-Garmsiri F, Emamgholipour S, Meshkani R. Folic acid ameliorates palmitate-induced inflammation through decreasing homocysteine and inhibiting NF-κB pathway in HepG2 cells. Arch Physiol Biochem. 2021 Feb 17:1-8. doi: 10.1080/13813455.2021.1878539. Epub ahead of print. PMID: 33596128.
2. Yang H, Qin D, Xu S, He C, Sun J, Hua J, Peng S. Folic acid promotes proliferation and differentiation of porcine pancreatic stem cells into insulin-secreting cells through canonical Wnt and ERK signaling pathway. J Steroid Biochem Mol Biol. 2021 Jan;205:105772. doi: 10.1016/j.jsbmb.2020.105772. Epub 2020 Oct 19. PMID: 33091596.
In vivo protocol:
1. Zhang L, Li Z, Xing C, Ma X, Xu R. The protective mechanism of folic acid on hyperhomocysteinemia-related arterial injury in spontaneously hypertensive rats: Folic acid against arterial inflammation. Vascular. 2021 Aug 6:17085381211036549. doi: 10.1177/17085381211036549. Epub ahead of print. PMID: 34362270.
2. Budni J, Moretti M, Freitas AE, Neis VB, Ribeiro CM, de Oliveira Balen G, Rieger DK, Leal RB, Rodrigues ALS. Behavioral and neurochemical effects of folic acid in a mouse model of depression induced by TNF-α. Behav Brain Res. 2021 Aug 3;414:113512. doi: 10.1016/j.bbr.2021.113512. Epub ahead of print. PMID: 34358572.
1: Diefenbach K, Trummer D, Ebert F, Lissy M, Koch M, Rohde B, Blode H. EE-drospirenone-levomefolate calcium versus EE-drospirenone + folic acid: folate status during 24 weeks of treatment and over 20 weeks following treatment cessation. Int J Womens Health. 2013 Apr 11;5:149-63. doi: 10.2147/IJWH.S37254. Print 2013. PubMed PMID: 23610531; PubMed Central PMCID: PMC3628530.
2: Wiesinger H, Eydeler U, Richard F, Trummer D, Blode H, Rohde B, Diefenbach K. Bioequivalence evaluation of a folate-supplemented oral contraceptive containing ethinylestradiol/drospirenone/levomefolate calcium versus ethinylestradiol/drospirenone and levomefolate calcium alone. Clin Drug Investig. 2012 Oct 1;32(10):673-84. doi: 10.2165/11635280-000000000-00000. PubMed PMID: 22909145.
3: Bart S Sr, Marr J, Diefenbach K, Trummer D, Sampson-Landers C. Folate status and homocysteine levels during a 24-week oral administration of a folate-containing oral contraceptive: a randomized, double-blind, active-controlled, parallel-group, US-based multicenter study. Contraception. 2012 Jan;85(1):42-50. doi: 10.1016/j.contraception.2011.05.013. Epub 2011 Jul 13. PubMed PMID: 22067790.
4: Blode H, Klipping C, Richard F, Trummer D, Rohde B, Diefenbach K. Bioequivalence study of an oral contraceptive containing ethinylestradiol/drospirenone/levomefolate calcium relative to ethinylestradiol/drospirenone and to levomefolate calcium alone. Contraception. 2012 Feb;85(2):177-84. doi: 10.1016/j.contraception.2011.05.015. Epub 2011 Jul 19. PubMed PMID: 22067789.
5: Rapkin RB, Creinin MD. The combined oral contraceptive pill containing drospirenone and ethinyl estradiol plus levomefolate calcium. Expert Opin Pharmacother. 2011 Oct;12(15):2403-10. doi: 10.1517/14656566.2011.610791. Epub 2011 Aug 31. Review. PubMed PMID: 21877996.
6: Fruzzetti F. Beyaz®: an oral contraceptive fortified with folate. Womens Health (Lond). 2012 Jan;8(1):13-9. doi: 10.2217/whe.11.68. Review. PubMed PMID: 22171769.
7: Nelson AL. Comprehensive evaluation of Safyral(®) 2012. Womens Health (Lond). 2012 Nov;8(6):619-33. doi: 10.2217/whe.12.50. Review. PubMed PMID: 23181528.
