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CHEBI:44185 - methotrexate
| Formula | C20H22N8O5 |
| Net Charge | 0 |
| Average Mass | 454.447 |
| Monoisotopic Mass | 454.17132 |
| SMILES | CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 |
| 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 |
| Wikipedia |
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| Roles Classification |
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| Chemical Role: | Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization. antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. EC 1.5.1.3 (dihydrofolate reductase) inhibitor An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3). anti-HIV agent An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus. antiviral agent A substance that destroys or inhibits replication of viruses. DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. |
| Applications: | cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume. abortifacient A chemical substance that interrupts pregnancy after implantation. antipsychotic agent Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. dermatologic drug A drug used to treat or prevent skin disorders or for the routine care of skin. antipsoriatic A drug used to treat psoriasis. antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. ophthalmology drug Any compound used for the treatment of eye conditions or eye diseases. anti-inflammatory agent Any compound that has anti-inflammatory effects. antifibrotic agent Any agent which acts to reduce fibrosis. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antirheumatic drug A drug used to treat rheumatoid arthritis. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. anti-anaemic agent A compound which increases either the number of red cells or the amount of haemoglobin in the blood. gout suppressant A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout. anti-asthmatic agent Any compound that has anti-asthmatic effects. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| methotrexate (CHEBI:44185) has functional parent L-glutamic acid (CHEBI:16015) |
| methotrexate (CHEBI:44185) has role abortifacient (CHEBI:50691) |
| methotrexate (CHEBI:44185) has role anti-anaemic agent (CHEBI:75835) |
| methotrexate (CHEBI:44185) has role anti-asthmatic agent (CHEBI:65023) |
| methotrexate (CHEBI:44185) has role anti-HIV agent (CHEBI:64946) |
| methotrexate (CHEBI:44185) has role anti-inflammatory agent (CHEBI:67079) |
| methotrexate (CHEBI:44185) has role antifibrotic agent (CHEBI:233423) |
| methotrexate (CHEBI:44185) has role antimalarial (CHEBI:38068) |
| methotrexate (CHEBI:44185) has role antimetabolite (CHEBI:35221) |
| methotrexate (CHEBI:44185) has role antineoplastic agent (CHEBI:35610) |
| methotrexate (CHEBI:44185) has role antipsoriatic (CHEBI:50748) |
| methotrexate (CHEBI:44185) has role antipsychotic agent (CHEBI:35476) |
| methotrexate (CHEBI:44185) has role antirheumatic drug (CHEBI:35842) |
| methotrexate (CHEBI:44185) has role antiviral agent (CHEBI:22587) |
| methotrexate (CHEBI:44185) has role cardiovascular drug (CHEBI:35554) |
| methotrexate (CHEBI:44185) has role dermatologic drug (CHEBI:50177) |
| methotrexate (CHEBI:44185) has role DNA synthesis inhibitor (CHEBI:59517) |
| methotrexate (CHEBI:44185) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683) |
| methotrexate (CHEBI:44185) has role gout suppressant (CHEBI:35845) |
| methotrexate (CHEBI:44185) has role immunosuppressive agent (CHEBI:35705) |
| methotrexate (CHEBI:44185) has role ophthalmology drug (CHEBI:66981) |
| methotrexate (CHEBI:44185) is a dicarboxylic acid (CHEBI:35692) |
| methotrexate (CHEBI:44185) is a monocarboxylic acid amide (CHEBI:29347) |
| methotrexate (CHEBI:44185) is a pteridines (CHEBI:26373) |
| methotrexate (CHEBI:44185) is conjugate acid of methotrexate(1−) (CHEBI:50680) |
| Incoming Relation(s) |
| methotrexate(1−) (CHEBI:50680) is conjugate base of methotrexate (CHEBI:44185) |
| IUPAC Name |
|---|
| N-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)-L-glutamic acid |
| INNs | Source |
|---|---|
| methotrexate | KEGG DRUG |
| methotrexatum | ChemIDplus |
| metotrexato | ChemIDplus |
| Synonyms | Source |
|---|---|
| 4-amino-10-methylfolic acid | ChemIDplus |
| 4-amino-N10-methylpteroylglutamic acid | NIST Chemistry WebBook |
| ADX-2191 | ChEMBL |
| CL 14377 | ChEMBL |
| CL-14377 | ChEMBL |
| D-amethopterin | ChEMBL |
| Brand Names | Source |
|---|---|
| Ebetrex | ChEMBL |
| Emtexate | DrugBank |
| Emtexate high-pot | ChEMBL |
| Emtexate pf | ChEMBL |
| Ledertrexate | DrugBank |
| Maxtrex | ChEMBL |
| Citations |
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