60388-53-6
Chemical Structure
(±)-Methotrexate
Synonym(s): (±)-Amethopterin; (±)-CL14377; (±)-WR19039
- CAS No.: 60388-53-6
- Formula:C20H22N8O5
- Molecular Weight:454.44
IUPAC Name: (4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)glutamic acid
InChIKey: FBOZXECLQNJBKD-UHFFFAOYSA-N
SMILES: O=C(C(CCC(O)=O)NC(C1=CC=C(C=C1)N(C)CC2=NC3=C(N=C(N=C3N=C2)N)N)=O)O
Biological Activity: (±)-Methotrexate ((±)-Amethopterin; (±)-CL14377; (±)-WR19039) is the racemate of Methotrexate (HY-14519). Methotrexate is an orally active antifolate (Antifolate). Methotrexate inhibits dihydrofolate reductase (DHFR), blocks tetrahydrofolate production, suppresses purine/pyrimidine synthesis and transmethylation, and causes intracellular accumulation of AICAR. Methotrexate promotes extracellular adenosine release, regulates the cytokine network, and inhibits the alarmin function of HMGB1. Methotrexate induces apoptosis and cytotoxicity, upregulates the expression of iNOS and COX-2, suppresses hippocampal neurogenesis, and induces pulmonary fibrosis. Methotrexate is used in the research of various immune and inflammation-related diseases such as arthritis, psoriasis, systemic lupus erythematosus, as well as pulmonary fibrosis and breast cancer[1][2][3][4][5].
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(±)-Methotrexate | (±)-Methotrexate ((±)-Amethopterin; (±)-CL14377; (±)-WR19039) is the racemate of Methotrexate (HY-14519). Methotrexate is an orally active antifolate (Antifolate). Methotrexate inhibits dihydrofolate reductase (DHFR), blocks tetrahydrofolate production, suppresses purine/pyrimidine synthesis and transmethylation, and causes intracellular accumulation of AICAR. Methotrexate promotes extracellular adenosine release, regulates the cytokine network, and inhibits the alarmin function of HMGB1. Methotrexate induces apoptosis and cytotoxicity, upregulates the expression of iNOS and COX-2, suppresses hippocampal neurogenesis, and induces pulmonary fibrosis. Methotrexate is used in the research of various immune and inflammation-related diseases such as arthritis, psoriasis, systemic lupus erythematosus, as well as pulmonary fibrosis and breast cancer. | |||||||||||||||||||||
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(±)-Methotrexate-d3 | (±)-Methotrexate-d3 ((±)-Amethopterin-d3; (±)-CL14377-d3; (±)-WR19039-d3) is the deuterated-labeled (±)-Methotrexate (HY-121151). (±)-Methotrexate is the racemate of Methotrexate (HY-14519). Methotrexate is an orally active antifolate (Antifolate). Methotrexate inhibits dihydrofolate reductase (DHFR), blocks tetrahydrofolate production, suppresses purine/pyrimidine synthesis and transmethylation, and causes intracellular accumulation of AICAR. Methotrexate promotes extracellular adenosine release, regulates the cytokine network, and inhibits the alarmin function of HMGB1. Methotrexate induces apoptosis and cytotoxicity, upregulates the expression of iNOS and COX-2, suppresses hippocampal neurogenesis, and induces pulmonary fibrosis. Methotrexate is used in the research of various immune and inflammation-related diseases such as arthritis, psoriasis, systemic lupus erythematosus, as well as pulmonary fibrosis and breast cancer. | |||||||||||||||||||||
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(±)-Methotrexate-13C,d3 disodium | (±)-Methotrexate-13C,d3 disodium ((±)-Amethopterin-13C,d3 disodium; (±)-CL14377-13C,d3 disodium; (±)-WR19039-13C,d3 disodium) is the deuterated, 13C-labeled (±)-Methotrexate (HY-121151). (±)-Methotrexate is the racemate of Methotrexate (HY-14519). Methotrexate is an orally active antifolate (Antifolate). Methotrexate inhibits dihydrofolate reductase (DHFR), blocks tetrahydrofolate production, suppresses purine/pyrimidine synthesis and transmethylation, and causes intracellular accumulation of AICAR. Methotrexate promotes extracellular adenosine release, regulates the cytokine network, and inhibits the alarmin function of HMGB1. Methotrexate induces apoptosis and cytotoxicity, upregulates the expression of iNOS and COX-2, suppresses hippocampal neurogenesis, and induces pulmonary fibrosis. Methotrexate is used in the research of various immune and inflammation-related diseases such as arthritis, psoriasis, systemic lupus erythematosus, as well as pulmonary fibrosis and breast cancer. | |||||||||||||||||||||
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References
- [1]. Cronstein BN, et al. The mechanism of action of methotrexate. Rheumatic diseases clinics of North America. 1997 Nov;23(4):739-55. [Content Brief]
- [2]. Bedoui Y, et al. Methotrexate an Old Drug with New Tricks. International journal of molecular sciences. 2019 Oct 10;20(20):5023. [Content Brief]
- [3]. Feagan B G, Rochon J, Fedorak R N, et al. Methotrexate for the Treatment of Crohn's Disease. N Engl J Med, 1995, 332(5): 292-297.
- [4]. Ohbayashi M, et al. Induction of pulmonary fibrosis by methotrexate treatment in mice lung in vivo and in vitro. The Journal of toxicological sciences. 2010 Oct;35(5):653-61. [Content Brief]
- [5]. Yang M, et al. Acute treatment with methotrexate induces hippocampal dysfunction in a mouse model of breast cancer. Brain research bulletin. 2012 Oct 01;89(1-2):50-6. [Content Brief]
