59-05-2
59-05-2
Chemical Structure
Methotrexate
Synonym(s): Amethopterin; CL14377; WR19039
- CAS No.: 59-05-2
- Formula:C20H22N8O5
- Molecular Weight:454.44
IUPAC Name: (4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamic acid
InChIKey: FBOZXECLQNJBKD-ZDUSSCGKSA-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
Biological Activity: Methotrexate (Amethopterin; CL14377; WR19039) 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].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Methotrexate | 99.95% | Methotrexate (Amethopterin; CL14377; WR19039) 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 (Standard) | 99.97% | Methotrexate (Standard) (Amethopterin (Standard); CL14377 (Standard); WR19039 (Standard)) is the analytical standard of Methotrexate (HY-14519). This product is intended for research and analytical applications. Methotrexate (Amethopterin; CL14377; WR19039) 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 diammonium | 99.69% | Methotrexate-d3 diammonium is the deuterated-labeled Methotrexate (HY-14519). Methotrexate (Amethopterin; CL14377; WR19039) 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 | 99.83% | Methotrexate-d3 is the deuterated-labeled Methotrexate (HY-14519). Methotrexate (Amethopterin; CL14377; WR19039) 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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Ornithine-methotrexate | Ornithine-methotrexate is an active compound. | |||||||||||||||||||||
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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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Diazoketone methotrexate | Diazoketone methotrexate, an analog of methotrexate, is an antitumor agent. Diazoketone methotrexate inhibits cell growth and inhibits synthesis of thymidylate. | |||||||||||||||||||||
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7-Hydroxymethotrexate-d3 | 7-Hydroxymethotrexate-d3 is the deuterium labeled 7-Hydroxymethotrexate. 7-Hydroxymethotrexate is a major metabolite of Methotrexate (HY-14519). Methotrexate, an antimetabolite and antifolate agent, inhibits the enzyme dihydrofolate reductase, thereby preventing the conversion of folic acid into tetrahydrofolate, and inhibiting DNA synthesis. | |||||||||||||||||||||
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Methotrexate γ-Methyl Ester | 98.30% | Methotrexate γ-Methyl Ester (Methotrexate 5-methyl ester) is an impurity of the folate antagonist Methotrexate (HY-14519). | ||||||||||||||||||||
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Methotrexate impurity 5 | Methotrexate impurity 5 (Methotrexate α-Methyl Ester) is an impurity of Methotrexate. | |||||||||||||||||||||
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Chloromethylketone methotrexate | Chloromethylketone methotrexate is an active compound. | |||||||||||||||||||||
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5-Monobutyl methotrexate | 5-Monobutyl methotrexate (NSC 305986; γ-MBMTX) is a dihydrofolate reductase (DHFR) inhibitor and esterase substrate. 5-Monobutyl methotrexate is hydrolyzed by esterases to produce methotrexate. In rhesus monkeys, 5-Monobutyl methotrexate clears more slowly from cerebrospinal fluid than from serum, and its serum protein binding rate exceeds 99%. At the same dose rate, 5-Monobutyl methotrexate achieves cerebrospinal fluid concentrations comparable to those of Methotrexate (HY-14519), and exhibits activity against Methotrexate-resistant cells (with transport defects) that is comparable to that against sensitive parental cells. 5-Monobutyl methotrexate can be used in studies related to Methotrexate-resistant tumors. | |||||||||||||||||||||
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Aminopterin | 98.67% | Aminopterin (4-Aminofolic acid), the 4-amino derivative of folic acid, is a folic acid antagonist. Aminopterin catalyses the reduction of folic acid to tetrahydrofolic acid, and competitively inhibits dihydrofolate reductase (DHFR) with a Ki of 3.7 pM. Aminopterin has anticancer and immunosuppressive activity. Aminopterin is used in treatment of pediatric leukemia. | ||||||||||||||||||||
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Methotrexate impurity 4 | Methotrexate impurity 4 is an impurity of Methotrexate. | |||||||||||||||||||||
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(R)-Methotrexate-d3 | (R)-Methotrexate-d3 is the deuterium labeled (R)-Methotrexate. | |||||||||||||||||||||
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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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Lysine-methotrexate | Lysine-methotrexate, an analogue of Methotrexate (HY-14519), is a dihydrofolate reductase (DHFR) inhibitor. | |||||||||||||||||||||
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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]
