MTX
METHOTREXATE
Find entries where: MTX
is present as a standalone ligand in 82 entries
as a non-polymer is covalently linked to polymer or other heterogen groups 2 entries
Chemical Component Summary | |
|---|---|
| Name | METHOTREXATE |
| Identifiers | (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]phenyl]carbonylamino]pentanedioic acid |
| Formula | C20 H22 N8 O5 |
| Molecular Weight | 454.439 |
| Type | NON-POLYMER |
| Isomeric SMILES | CN(Cc1cnc2c(n1)c(nc(n2)N)N)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O |
| InChI | InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1 |
| InChIKey | FBOZXECLQNJBKD-ZDUSSCGKSA-N |
Chemical Details | |
|---|---|
| Formal Charge | 0 |
| Atom Count | 55 |
| Chiral Atom Count | 1 |
| Bond Count | 57 |
| Aromatic Bond Count | 17 |
Drug Info: DrugBank
| DrugBank ID | DB00563? |
|---|---|
| Name | Methotrexate |
| Groups | approved |
| Description | Methotrexate is a folate derivative that inhibits several enzymes responsible for nucleotide synthesis.[A180322] This inhibition leads to suppression of inflammation as well as prevention of cell division.[A180322] Because of these effects, methotrexate is often used to treat inflammation caused by arthritis or to control cell division in neoplastic diseases such as breast cancer and non-Hodgkin's lymphoma.[A180322,L7144,L7147,L7150,L7180] Due to the toxic effects of methotrexate, it is indicated for treatment of some forms of arthritis and severe psoriasis only if first line treatment has failed or patients are intolerant of those treatments.[L7180] Methotrexate was granted FDA approval on 7 December 1953.[L7198] |
| Synonyms |
|
| Brand Names |
|
| Indication | Methotrexate oral solution is indicated for pediatric acute lymphoblastic leukemia and pediatric polyarticular juvenile idiopathic arthritis.[L7144] Methotrexate injections for subcutaneous use are indicated for severe active rheumatoid arthritis, polyarticular juvenile idiopathic arthritis and severe, recalcitrant, disabling psoriasis.[L7147,L7150,L10457] It has also been approved by the EMA for the treatment of adult patients requiring systemic therapy for moderate-to-severe plaque psoriasis.[L48796] Other formulations are indicated to treat gestational choriocarcinoma, chorioadenoma destruens, hydatiform mole, breast cancer, epidermoid cancer of the head and neck, advanced mycosis fungoides, lung cancer, and advanced non-Hodgkin's lymphoma.[L7180] It is also used in the maintenance of acute lymphocytic leukemia.[L7180] Methotrexate is also given before treatment with leucovorin to prolong relapse-free survival following surgical removal of a tumour in non-metastatic osteosarcoma.[L7180] |
| Categories |
|
| ATC-Code |
|
| CAS number | 59-05-2 |
Drug Targets
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| Thymidylate synthase | MPVAGSELPRRPLPPAAQERDAEPRPPHGELQYLGQIQHILRCGVRKDDR... | unknown | inhibitor |
| Bifunctional purine biosynthesis protein PURH | MAPGQLALFSVSDKTGLVEFARNLTALGLNLVASGGTAKALRDAGLAVRD... | unknown | inhibitor |
| Dihydrofolate reductase | MVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL... | unknown | inhibitor |
| Dihydrofolate reductase | MVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL... | unknown | substrate |
| Aldehyde oxidase | MDRASELLFYVNGRKVIEKNVDPETMLLPYLRKKLRLTGTKYGCGGGGCG... | unknown | substrate |
| View More | |||
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison
T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS.
Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682
Related Resource References
| Resource Name | Reference |
|---|---|
| Pharos | CHEMBL34259 |
| PubChem | 126941 |
| ChEMBL | CHEMBL34259 |
| ChEBI | CHEBI:44185 |
