6745-93-3
Chemical Structure
Methotrexate monohydrate
Synonym(s): Amethopterin monohydrate; CL14377 monohydrate; WR19039 monohydrate
- CAS No.: 6745-93-3
- Formula:C20H24N8O6
- Molecular Weight:472.45
IUPAC Name: (4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamic acid hydrate
InChIKey: FPJYMUQSRFJSEW-ZOWNYOTGSA-N
SMILES: NC1=NC(N)=C2C(N=CC(CN(C)C3=CC=C(C(N[C@@H](CCC(O)=O)C(O)=O)=O)C=C3)=N2)=N1.O
Biological Activity: Methotrexate monohydrate (Amethopterin monohydrate; CL14377 monohydrate; WR19039 monohydrate) is an orally active antifolate (Antifolate). Methotrexate monohydrate inhibits dihydrofolate reductase (DHFR), blocks tetrahydrofolate production, suppresses purine/pyrimidine synthesis and transmethylation, and causes intracellular accumulation of AICAR. Methotrexate monohydrate promotes extracellular adenosine release, regulates the cytokine network, and inhibits the alarmin function of HMGB1. Methotrexate monohydrate induces apoptosis and cytotoxicity, upregulates the expression of iNOS and COX-2, suppresses hippocampal neurogenesis, and induces pulmonary fibrosis. Methotrexate monohydrate 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 monohydrate | Methotrexate monohydrate (Amethopterin monohydrate; CL14377 monohydrate; WR19039 monohydrate) is an orally active antifolate (Antifolate). Methotrexate monohydrate inhibits dihydrofolate reductase (DHFR), blocks tetrahydrofolate production, suppresses purine/pyrimidine synthesis and transmethylation, and causes intracellular accumulation of AICAR. Methotrexate monohydrate promotes extracellular adenosine release, regulates the cytokine network, and inhibits the alarmin function of HMGB1. Methotrexate monohydrate induces apoptosis and cytotoxicity, upregulates the expression of iNOS and COX-2, suppresses hippocampal neurogenesis, and induces pulmonary fibrosis. Methotrexate monohydrate 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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- [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]
Keywords
