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QuickView for Methotrexate (compound)


PubChem
Name: Methotrexate
PubChem Compound ID: 126941
Description: An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of TETRAHYDROFOLATE DEHYDROGENASE and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA.
Molecular formula: C20H22N8O5
Molecular weight: 454.44 g/mol
Synonyms:
SPBio_001094; 59-05-2; KBio2_002338; AIDS-006948; MTX; SPBio_002149; KBio1_000114; N-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)-L-glutamic acid; CHEBI:6837; Methotrexate.
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DrugBank
Identification
Name: Methotrexate
Name (isomeric): DB00563
Drug Type: small molecule
Description: An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of TETRAHYDROFOLATE DEHYDROGENASE and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA.
Synonyms:
MTX; HDMTX; Methotrexate Sodium; Amethopterine; Methylaminopterinum; N-Bismethylpteroylglutamic Acid; Methylaminopterin; Methotrexat; Methopterin; Methotextrate.
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Brand: Metatrexan, Trexall, Rheumatrex, Mexate, Abitrexate, Folex, Methotrate, Ledertrexate, Arbitrexate, Emtexate, Antifolan
Category: Antimetabolites, Antimetabolites, Antineoplastic, Antineoplastic Agents, Abortifacient Agents, Enzyme Inhibitors, Abortifacient Agents, Nonsteroidal, Folic Acid Antagonists, Antirheumatic Agents, Immunosuppressive Agents, Dermatologic Agents, Nucleic Acid Synthesis Inhibitors
CAS number: 59-05-2
Pharmacology
Indication: For the treatment of gestational choriocarcinoma, chorioadenoma destruens and hydatidiform mole. Also for the treatment of severe psoriasis and severe, active, classical or definite rheumatoid arthritis.
Pharmacology:
Methotrexate is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Methotrexate inhibits folic acid reductase which is respon...
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Mechanism of Action: Methotrexate anti-tumor activity is a result of the inhibition of folic acid reductase, leading to inhibition of DNA synthesis and inhibition of cellular replication. The mechanism involved in its activity against rheumatoid arthritis is not known.
Absorption: Generally well absorbed with a mean bioavailability of about 60%.
Protein binding: 50%, primarily to albumin
Biotransformation: Hepatic.
Route of elimination: With IV administration, 80% to 90% of the administered dose is excreted unchanged in the urine within 24 hours. There is limited biliary excretion amounting to 10% or less of the administered dose.
Half Life: Low doses: 3 to 10 hours; High doses: 8 to 15 hours.
Toxicity: Symptoms of overdose include bone marrow suppression and gastrointestinal toxicity. LD50=43mg/kg(orally in rat).
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Take without regard to meals. Limit caffeine intake.
Milk appears to reduce its absorption.
Drug interaction:
DiclofenacThe NSAID, diclofenac, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
SulfathiazoleThe sulfamide increases the toxicity of methotrexate
AmoxicillinThe penicillin increases the effect and toxicity of methotrexate
ClavulanateThe penicillin increases the effect and toxicity of methotrexate
OmeprazoleOmeprazole increases the levels of methotrexate
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