Methotrexate

USDailyMed:Methotrexate AU:D L01BA01(WHO)L04AX03(WHO) AU:S4(Prescription only)CA:℞-onlyUK:POM(Prescription only)US:℞-onlyEU:Rx-onlyIn general: ℞ (Prescription only) (2S)-2-[(4-{[(2,4-Diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)amino]pentanedioic acid 59-05-2Y 126941 4815 DB00563Y 112728Y YL5FZ2Y5U1 D00142Y CHEBI:44185Y ChEMBL34259Y MTX (PDBe,RCSB PDB) DTXSID4020822 Interactive image 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=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/s1YKey:FBOZXECLQNJBKD-ZDUSSCGKSA-NY Methotrexate, formerly known asamethopterin, is achemotherapy agentandimmune-system suppressant. It is used to treatcancer,autoimmune diseases, andectopic pregnancies. It is used for cancers such asbreast cancer,leukemia,lung cancer,lymphoma,gestational trophoblastic disease, andosteosarcoma, as well as autoimmune diseases such aspsoriasis,rheumatoid arthritis, andCrohn's disease. It can be givenby mouthor by injection. Common side effects include nausea, feeling tired, fever, increased risk of infection,low white blood cell counts, andbreakdown of the skin inside the mouth. Other side effects may includeliver disease,lung disease, lymphoma, and severe skin rashes. People on long-term treatment should be regularly checked for side effects. It is not safe duringbreastfeeding. In those withkidney problems, lower doses may be needed. It acts by blocking the body's use offolic acid, so taking folic acid supplements can reduce its effectiveness.Folinic acid(leucovorin) is used to reduce the side effects of methotrexate (rescue therapy). Methotrexate was first made in 1947 and initially was used to treat cancer, as it was less toxic than the then-current treatments.In 1956 it provided the first cures of a metastatic cancer.It is on theWorld Health Organization's List of Essential Medicines.Methotrexate is available as ageneric medication.In 2023, it was the 130th most commonly prescribed medication in the United States, with more than 4million prescriptions.