Levomefolna kiselina

Levomefolna kiselina
	(2S)-2-[ [4-[(2-Amino-5-metil-4-okso-1,6,7,8-tetrahidropteridin-6-il) metilamino]benzoil]amino]pentandionska kiselina
Drugi nazivi	5-metiltetrahidrofolna kiselina (5-Me-THFA, 5-Me-H4FA),; anjon: 5-metiltetrahidrofolat (5-Me-THF, 5-Me-H4F), L-metilfolat; Metafolin, Ekstrafolat-S
Identifikacija
CAS registarski broj	134-35-0, 151533-22-1 (kalcijumova so)
PubChem	444412, ; 15341110 (kalcijumova so)
ChemSpider	388371
UNII	8S95DH25XC
KEGG	D09353
MeSH	5-methyltetrahydrofolate
ATC code	B03BB51
Jmol-3D slike	Slika 1
SMILES
	O=C(O)[C@H](NC(=O)c1ccc(cc1)NCC3N(/C2=C(/N/C(=N\C2=O)N)NC3)C)CCC(=O)O
InChI
	InChI=1S/C20H25N7O6/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)/t12?,13-/m1/s1 ; Kod: ZNOVTXRBGFNYRX-ZGTCLIOFSA-N InChI=1/C20H25N7O6/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)/t12?,13-/m1/s1; Kod: ZNOVTXRBGFNYRX-ZGTCLIOFBZ
Svojstva
Molekulska formula	C20H25N7O6
Molarna masa	459.46 g mol−1
Farmakologija
Načini upotrebe	oralno, transdermalno, supkutano
	; ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Levomefolinska kiselina (5-MTHF, l-metilfolat i 5-metiltetrahidrofolat) je prirodna, aktivna forma folne kiseline koja se koristi na ćelijskom nivou za reprodukciju DNK, cisteinski ciklis i regulaciju homocisteina, kao i niz drugih funkcija. Nemetilisana forma, folne kiseline (vitamina B₉), je sintetički folat koji je prisutan u nutricionim suplementima. Sintetička folna kiselina se metaboliše u telu u levomefolinsku kiselinu.

Ona se sintetiše u apsorptivnim ćelijama tankih creva iz poliglutaminisanog dijetarnog folata. Ona je metilisani derivat tetrahidrofolata (THF, H₄F). Levomefolinska kiselina se formira posredstvom metilentetrahidrofolatne reduktaze (MTHFR) iz 5,10-metilentetrahidrofolata (5,10-CH₂-THF, MTHF) i koristi se za reciklaciju homocisteina nazad u metionin pomoću 5-metiltetrahidrofolat-homocistein metiltransferaze (MTR), takođe poznate kao metionin sintaza (MS).^[6]

Levomefolinska kiselina je predložena kao mogući tretman za kardiovaskularne bolesti^[7]^[8] i uznapredovalih kancera dojki i kolorektalnih kancera.

Levomefolat kalcijum, kalcijumska so levomefolinske kiseline, je u prodaji pod imenima Metafolin i Deplin.^[9]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ „Folate / Folinic Acid”, Neurobiologix website, pristupljeno 25. 9. 2012
↑ „5-methyltetrahydrofolate - Compound Summary”, PubChem (NCBI), pristupljeno 25. 9. 2012
↑ Willems, Frank F; Boers GHJ, Blom HJ, Aengevaeren WRM, Verheugt FWA (2004). „Pharmacokinetic study on the utilisation of 5-methyltetrahydrofolate and folic acid in patients with coronary artery disease”. Br J Pharmacol (Nature Publishing Group) 145 (5): 825–830. DOI:10.1038/sj.bjp.0705446. PMC 1574248. PMID 14769778. >
↑ Iris P Fohr, Reinhild Prinz-Langenohl, Anja Brönstrup, Anja M Bohlmann, Heinz Nau, Heiner K Berthold, and Klaus Pietrzik, IP; Prinz-Langenohl, R; Brönstrup, A; Bohlmann, AM; Nau, H; Berthold, HK; Pietrzik, K (2002). „5,10-Methylenetetrahydrofolate reductase genotype determines the plasma homocysteine-lowering effect of supplementation with 5-methyltetrahydrofolate or folic acid in healthy young women”. Am J Clin Nutr (American Society for Clinical Nutrition) 75 (2): 275–282. PMID 11815318.
↑ Lakely, Susan. „RPH”. L-Methylfolate. Pristupljeno 12. 1. 2012.

Povezano

5-Metiltetrahidrofolat-homocistein metiltransferaza (MTR)
S-Adenozilmetionin (SAMe)
Metilentetrahidrofolatna reduktaza (MTHFR)
5,10-Metilentetrahidrofolat (5,10-CH₂-THF, MTHF)

Spoljašnje veze

Portal Hemija

Calcium L-5-Methyltetrahydrofolate (L-5-MTHF-Ca)
Localized depletion: the key to colorectal cancer risk mediated by MTHFR genotype and folate?
Stahl, SM (October 2007). „Novel Therapeutics for Depression: L-methylfolate as a Trimonoamine Modulator and Antidepressant-Augmenting Agent”. CNS Spectrums 12 (10): 739–744. PMID 17934378.

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[neurobiologix-folate-5] „Folate / Folinic Acid”, Neurobiologix website, pristupljeno 25. 9. 2012

[pubchem444412-6] „5-methyltetrahydrofolate - Compound Summary”, PubChem (NCBI), pristupljeno 25. 9. 2012

[7] Willems, Frank F; Boers GHJ, Blom HJ, Aengevaeren WRM, Verheugt FWA (2004). „Pharmacokinetic study on the utilisation of 5-methyltetrahydrofolate and folic acid in patients with coronary artery disease”. Br J Pharmacol (Nature Publishing Group) 145 (5): 825–830. DOI:10.1038/sj.bjp.0705446. PMC 1574248. PMID 14769778. >

[8] Iris P Fohr, Reinhild Prinz-Langenohl, Anja Brönstrup, Anja M Bohlmann, Heinz Nau, Heiner K Berthold, and Klaus Pietrzik, IP; Prinz-Langenohl, R; Brönstrup, A; Bohlmann, AM; Nau, H; Berthold, HK; Pietrzik, K (2002). „5,10-Methylenetetrahydrofolate reductase genotype determines the plasma homocysteine-lowering effect of supplementation with 5-methyltetrahydrofolate or folic acid in healthy young women”. Am J Clin Nutr (American Society for Clinical Nutrition) 75 (2): 275–282. PMID 11815318.

[eMedTV-9] Lakely, Susan. „RPH”. L-Methylfolate. Pristupljeno 12. 1. 2012.

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