Methotrexate

Methotrexate
Clinical data


Pronunciation	ⁱ/ˌmɛθəˈtrɛkˌseɪt, ˌmiː-, -θoʊ-/
Trade names	Trexall, Rheumatrex, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682019
License data	US FDA: Methotrexate
Pregnancy category	AU: D US: X (Contraindicated)
Routes of administration	, IV, IM, SC, intrathecal
ATC code	L01BA01 (WHO) L04AX03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	60% at lower doses, less at higher doses.
Protein binding	35–50% (parent drug), 91–93% (7-hydroxymethotrexate)
Metabolism	Hepatic and intracellular
Biological half-life	3–10 hours (lower doses), 8–15 hours (higher doses)
Excretion	Urine (80–100%), faeces (small amounts)
Identifiers
IUPAC name (2S)-2-[(4-{[(2,4-Diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)amino]pentanedioic acid
CAS Number	59-05-2^Y
PubChem (CID)	126941
IUPHAR/BPS	4815
DrugBank	DB00563^Y
ChemSpider	112728^Y
UNII	YL5FZ2Y5U1^Y
KEGG	D00142^Y
ChEBI	CHEBI:44185^Y
ChEMBL	CHEMBL34259^Y
ECHA InfoCard	100.000.376
Chemical and physical data
Formula	C₂₀H₂₂N₈O₅
Molar mass	454.44 g/mol
3D model (Jmol)	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^Y Key:FBOZXECLQNJBKD-ZDUSSCGKSA-N^Y

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

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. Other side effects may include liver disease, lung disease, lymphoma, and severe skin rashes. People on long-term treatment should be regularly checked for side effects. It is not safe during breastfeeding. In those with kidney problems, lower doses may be needed. It acts by blocking the body's use of folic acid.

Methotrexate was made in 1947 and initially came into medical use to treat cancer, as it was less toxic than the current treatments. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Methotrexate is available as a generic medication. The wholesale cost as of 2014 in the developing world is between US$0.06 and 0.36 per day for the form taken by mouth. In the United States, a typical month of treatment costs $25 to $50.

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