Details
Stereochemistry | EPIMERIC |
Molecular Formula | C19H23N7O6 |
Molecular Weight | 445.4292 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1
InChI
InChIKey=MSTNYGQPCMXVAQ-KIYNQFGBSA-N
InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1
Tetrahydrofolic acid is a folic acid derivative. It is produced from dihydrofolic acid by dihydrofolate reductase. It is converted into 5,10-methylenetetrahydrofolate by serine hydroxymethyltransferase. It is a coenzyme in many reactions, especially in the metabolism of amino acids and nucleic acids. It acts as a donor of a group with one carbon atom. It gets this carbon atom by sequestering formaldehyde produced in other processes. Tetrahydrofolate is the main active metabolite of dietary folate. It is vital as a coenzyme in reactions involving transfers of single carbon groups. Tetrahydrofolate has a role in nucleic and amino acid synthesis. As nucleic and amino acid synthesis is affected by a deficiency of tetrahydrofolate, actively dividing and growing cells tend to be the first affected. Tetrahydrofolate is used to treat topical sprue and megaloblastic and macrocytic anemias, hematologic complications resulting from a deficiency in folic acid. Tetrahydrofolic acid is used for nutritional supplementation, also for treating dietary shortage or imbalance.
Approval Year
PubMed
Title | Date | PubMed |
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The toxicity of tetrahydrohomofolic acid in normal and malaria-infected monkeys. | 1968 Feb |
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Thymidylate synthetase activity in the Novikoff hepatoma. | 1976 Dec |
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Molecular cloning of the human placental folate transporter. | 1995 Jan 17 |
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Sodium-dependent methotrexate carrier-1 is expressed in rat kidney: cloning and functional characterization. | 2004 Mar |
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Enzymatic properties of ALDH1L2, a mitochondrial 10-formyltetrahydrofolate dehydrogenase. | 2011 May 30 |
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Tetrahydrofolate recognition by the mitochondrial folate transporter. | 2011 Sep 9 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02639650
Tetrahydrofolic acid is used as a component of methotrexate chemotherapy treatment of Gestational Trophoblastic Neoplasms: methotrexate 100mg/m2, 200mg/m2, ivgtt, tetrahydrofolic acid (FA) 15mg q12h*4(24h after methotrexate injection),started at the first day of cycle, two weeks a cycle.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6129582
Tetrahydrofolic acid at 100 uM concentration didn`t significantly inhibit the specific binding of [3H]-KA to striatal membranes.
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Tetrahydrofolic acid
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ACTIVE MOIETY