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Methotrexate information


Methotrexate
Clinical data
Pronunciation/ˌmɛθəˈtrɛkˌst, ˌm-, -θ-/ [1][2][3]
Trade namesTrexall, Rheumatrex, Otrexup, others[4]
Other namesMTX, amethopterin
AHFS/Drugs.comMonograph
MedlinePlusa682019
License data
  • US DailyMed: Methotrexate
Pregnancy
category
  • AU: D
Routes of
administration
By mouth, intravenous (IV), intramuscular (IM), subcutaneous injection (SC), intrathecal
ATC code
  • L01BA01 (WHO) L04AX03 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[5]Rx-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability60% at lower doses, less at higher doses.[6]
Protein binding35–50% (parent drug),[6] 91–93% (7-hydroxymethotrexate)[7]
MetabolismHepatic and intracellular[6]
Elimination half-life3–10 hours (lower doses), 8–15 hours (higher doses)[6]
ExcretionUrine (80–100%), feces (small amounts)[6][7]
Identifiers
IUPAC name
  • (2S)-2-[(4-{[(2,4-Diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)amino]pentanedioic acid
CAS Number
  • 59-05-2 checkY
PubChem CID
  • 126941
IUPHAR/BPS
  • 4815
DrugBank
  • DB00563 checkY
ChemSpider
  • 112728 checkY
UNII
  • YL5FZ2Y5U1
KEGG
  • D00142 checkY
ChEBI
  • CHEBI:44185 checkY
ChEMBL
  • ChEMBL34259 checkY
PDB ligand
  • MTX (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID4020822 Edit this at Wikidata
ECHA InfoCard100.000.376 Edit this at Wikidata
Chemical and physical data
FormulaC20H22N8O5
Molar mass454.447 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C([C@H](CCC(O)=O)NC(C1=CC=C(N(CC2=CN=C(N=C(N)N=C3N)C3=N2)C)C=C1)=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 checkY
  • Key:FBOZXECLQNJBKD-ZDUSSCGKSA-N checkY
  (verify)

Methotrexate (MTX), formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant.[4] It is used to treat cancer, autoimmune diseases, and ectopic pregnancies.[4] Types of cancers it is used for include breast cancer, leukemia, lung cancer, lymphoma, gestational trophoblastic disease, and osteosarcoma.[4] Types of autoimmune diseases it is used for include psoriasis, rheumatoid arthritis, and Crohn's disease.[4] It can be given by mouth or by injection.[4]

Common side effects include nausea, feeling tired, fever, increased risk of infection, low white blood cell counts, and breakdown of the skin inside the mouth.[4] Other side effects may include liver disease, lung disease, lymphoma, and severe skin rashes.[4] People on long-term treatment should be regularly checked for side effects.[4] It is not safe during breastfeeding.[4] In those with kidney problems, lower doses may be needed.[4] It acts by blocking the body's use of folic acid.[4]

Methotrexate was first made in 1947 and initially was used to treat cancer, as it was less toxic than the then-current treatments.[8] In 1956 it provided the first cures of a metastatic cancer.[9] It is on the World Health Organization's List of Essential Medicines.[10][11] Methotrexate is available as a generic medication.[4] In 2021, it was the 132nd most commonly prescribed medication in the United States, with more than 4 million prescriptions.[12][13]

  1. ^ "methotrexate – definition of methotrexate in English from the Oxford dictionary". OxfordDictionaries.com. Archived from the original on 22 October 2012. Retrieved 20 January 2016.
  2. ^ "methotrexate". Merriam-Webster.com Dictionary.
  3. ^ "methotrexate". Dictionary.com Unabridged (Online). n.d.
  4. ^ a b c d e f g h i j k l m "Methotrexate". The American Society of Health-System Pharmacists. Archived from the original on 8 October 2016. Retrieved 22 August 2016.
  5. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  6. ^ a b c d e "Trexall, Rheumatrex (methotrexate) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 8 February 2014. Retrieved 12 April 2014.
  7. ^ a b Bannwarth B, Labat L, Moride Y, Schaeverbeke T (January 1994). "Methotrexate in rheumatoid arthritis. An update". Drugs. 47 (1): 25–50. doi:10.2165/00003495-199447010-00003. PMID 7510620. S2CID 46974070.
  8. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 251. ISBN 9780470015520. Archived from the original on 16 February 2017.
  9. ^ "Today's anti-cancer tools are ever better wielded". The Economist. 14 September 2017. Retrieved 16 September 2017.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  12. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  13. ^ "Methotrexate - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Methotrexate

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Methotrexate (MTX), formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant. It is used to treat cancer, autoimmune diseases...

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Folinic acid

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as leucovorin, is a medication used to decrease the toxic effects of methotrexate and pyrimethamine. It is also used in combination with 5-fluorouracil...

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Rheumatoid arthritis

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Disease-modifying antirheumatic drugs (DMARDs), such as hydroxychloroquine and methotrexate, may be used to try to slow the progression of disease. Biological DMARDs...

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Chemotherapy

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deoxynucleoside analogues and thiopurines. The anti-folates include methotrexate and pemetrexed. Methotrexate inhibits dihydrofolate reductase (DHFR), an enzyme that...

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Upadacitinib

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(DMARDs). Upadacitinib may be used as monotherapy or in combination with methotrexate. Upadacitinib was approved in January 2022, by the FDA for treating adults...

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Ectopic pregnancy

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to remove the fallopian tube all together. The use of the medication methotrexate works as well as surgery in some cases. Specifically it works well when...

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Sarcoidosis

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problems, steroids such as prednisone are indicated. Medications such as methotrexate, chloroquine, or azathioprine may occasionally be used in an effort to...

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Rheumatology

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such as infliximab and adalimumab, the TNF inhibitor etanercept, and methotrexate for moderate to severe rheumatoid arthritis. The biologic agent rituximab...

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Tocilizumab

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moderate to severe rheumatoid arthritis, applied in combination with methotrexate, if other drugs like disease-modifying antirheumatic drugs (DMARDs) and...

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Scleroderma

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treatment may improve symptoms. Medications used include corticosteroids, methotrexate, and non-steroidal anti-inflammatory drugs (NSAIDs). Outcome depends...

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Antiarthritics

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As such, it will help to reduce the side effects of methotrexate. Contraindications of methotrexate include: Patient with active infection Ascites Immunodeficiency...

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Psoriasis

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vitamin D3 cream, ultraviolet light, immunosuppressive drugs, such as methotrexate, and biologic therapies targeting specific immunologic pathways. About...

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Dermatomyositis

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corticosteroids family are typically used with other agents such as methotrexate or azathioprine recommended if steroids are not working well. Intravenous...

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Tetrahydrofolic acid

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dihydrofolic acid by dihydrofolate reductase. This reaction is inhibited by methotrexate. It is converted into 5,10-methylenetetrahydrofolate by serine hydroxymethyltransferase...

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Immunosuppressive drug

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synthesis of nucleic acids. These include: folic acid analogues, such as methotrexate purine analogues, such as azathioprine and mercaptopurine pyrimidine...

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Adjuvant therapy

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favorable survival outcomes that accompanied use of Cyclophosphamide Methotrexate Fluorouracil (CMF) after the initial mastectomy. In 1976, shortly after...

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Enzyme

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strongly resemble the real substrate of the enzyme. For example, the drug methotrexate is a competitive inhibitor of the enzyme dihydrofolate reductase, which...

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Yellapragada Subbarow

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adenosine triphosphate (ATP) as an energy source in the cell, developed methotrexate for the treatment of cancer and led the department at Lederle laboratories...

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Glucarpidase

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(Voraxaze) is a medication used for the treatment of elevated levels of methotrexate (defined as 1 micromol/L) during treatment of cancer patients who have...

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Folate

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with folate metabolism are used to treat cancer. The antifolate drug methotrexate is often used to treat cancer because it inhibits the production of the...

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Toxic leukoencephalopathy

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methotrexate even at low doses. In contrast to intravenous methotrexate for cancer patients, leukoencephalopathy induced by orally taken methotrexate...

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Primary central nervous system lymphoma

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addition of IV methotrexate and folinic acid (leucovorin) may extend survival to a median of 3.5 years. If radiation is added to methotrexate, median survival...

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Dihydrofolate reductase

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synthesis. Trimethoprim, an antibiotic, inhibits bacterial DHFR while methotrexate, a chemotherapy agent, inhibits mammalian DHFR. However, resistance has...

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Lymphoma

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the human immunodeficiency virus (HIV) Post-transplant Associated with methotrexate therapy Primary central nervous system lymphoma occurs most often in...

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Hypersensitivity

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cromoglycate, and environmental control. Experimentally, a low dose of methotrexate or cyclosporin and omalizumab (a monoclonal anti-IgE antibody) has been...

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