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Methotrexate
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| Pronunciation | /ˌmɛθəˈtrɛkˌseɪt, ˌmiː-, -θoʊ-/ ⓘ[1][2][3] |
| Trade names | Trexall, Rheumatrex, Otrexup, others[4] |
| Other names | MTX, amethopterin |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682019 |
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| Routes of administration | By mouth, intravenous, intramuscular, subcutaneous, intrathecal |
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| Pharmacokinetic data | |
| Bioavailability | 60% at lower doses, less at higher doses.[7] |
| Protein binding | 35–50% (parent drug),[7] 91–93% (7-hydroxymethotrexate)[8] |
| Metabolism | Hepatic and intracellular[7] |
| Elimination half-life | 3–10 hours (lower doses), 8–15 hours (higher doses)[7] |
| Excretion | Urine (80–100%), feces (small amounts)[7][8] |
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| ECHA InfoCard | 100.000.376 |
| Chemical and physical data | |
| Formula | C20H22N8O5 |
| Molar mass | 454.447 g·mol−1 |
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Methotrexate, 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.[9] In 1956 it provided the first cures of a metastatic cancer.[10] It is on the World Health Organization's List of Essential Medicines.[11] Methotrexate is available as a generic medication.[4] In 2022, it was the 132nd most commonly prescribed medication in the United States, with more than 4 million prescriptions.[12][13]
A photoswitchable analog of methotrexate has been developed (phototrexate) for photoactivated chemotherapy with localized illumination and reduced adverse effects.[14] Using proteasome-targeting technology, the MTX-PROTAC versortrexate (VSTX) selectively degrades dihydrofolate reductase (DHFR), the primary target of MTX.[15]
- ^ "methotrexate – definition of methotrexate in English from the Oxford dictionary". OxfordDictionaries.com. Archived from the original on 22 October 2012. Retrieved 20 January 2016.
- ^ "methotrexate". Merriam-Webster.com Dictionary. Merriam-Webster.
- ^ "methotrexate". Dictionary.com Unabridged (Online). n.d.
- ^ 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.
- ^ "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.
- ^ "Jylamvo EPAR". European Medicines Agency. 29 March 2017. Retrieved 25 June 2024.
- ^ 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.
- ^ 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.
- ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 251. ISBN 9780470015520. Archived from the original on 16 February 2017.
- ^ "Today's anti-cancer tools are ever better wielded". The Economist. 14 September 2017. Retrieved 16 September 2017.
- ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
- ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
- ^ "Methotrexate Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
- ^ Matera C, Gomila AM, Camarero N, Libergoli M, Soler C, Gorostiza P (November 2018). "Photoswitchable Antimetabolite for Targeted Photoactivated Chemotherapy". Journal of the American Chemical Society. 140 (46): 15764–15773. Bibcode:2018JAChS.14015764M. doi:10.1021/jacs.8b08249. hdl:2445/126377. PMID 30346152.
- ^ Rana, S., Dranchak, P., Dahlin, J.L., Lamy, L., Li, W., Oliphant, E., et al. (2024). "Methotrexate-based PROTACs as DHFR-specific chemical probes". Cell Chem. Biol. 31 (2): 221–33. doi:10.1016/j.chembiol.2023.09.014. PMC 10922102. PMID 37875111.
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