methotrexate

Also known as amethopterin, 4-amino-10-methylfolic acid, 4-amino-N(10)-methylpteroylglutamic acid, MTX, N-(4-{[(2,4-diamino-6-pteridinyl)methyl]methylamino}benzoyl)-L-glutamic acid

Methotrexate, formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant. It is used to treat cancer, autoimmune diseases, and ectopic pregnancies. Types of cancers it is used for include breast cancer, leukemia, lung cancer, lymphoma, gestational trophoblastic disease, 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.

Key facts

Drug.legal_status: Rx-only
Drug.Watchedfields: changed
Drug.verifiedrevid: 464193974
Drug.image: Methotrexate skeletal.svg
Drug.image_class: skin-invert-image
Drug.width: 300
Drug.image2: Methotrexate-from-xtal-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.width2: 300
Drug.tradename: Trexall, Rheumatrex, Otrexup, others
Drug.MedlinePlus: a682019
Drug.DailyMedID: Methotrexate
Drug.pregnancy_AU: D
Drug.routes_of_administration: By mouth, intravenous, intramuscular, subcutaneous, intrathecal
Drug.ATC_prefix: L01
Drug.ATC_suffix: BA01
Drug.legal_AU: S4
Drug.legal_CA: Rx-only

via Wikipedia infobox

Chemical data

Formula: C20H22N8O5
Molecular weight: 454.4 g/mol
IUPAC name: (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChIKey: FBOZXECLQNJBKD-ZDUSSCGKSA-N
XLogP: -1.8
Polar surface area: 211 Å²
H-bond donors: 5
H-bond acceptors: 12
Formal charge: 0

via PubChem

Research

66,595 papers

The mechanism of action of methotrexate.Rheumatic diseases clinics of North America · 1997
Methotrexate polyglutamates.Expert review of clinical pharmacology · 2024
Molecular mechanism of action and pharmacokinetic properties of methotrexate.Molecular biology reports · 2020
Methotrexate therapy.Canadian journal of gastroenterology = Journal canadien de gastroenterologie · 1998
Methotrexate: Use in the Post Dobbs v. Jackson Era.Journal of clinical rheumatology : practical reports on rheumatic & musculoskeletal diseases · 2024

via PubMed

Wikidata facts

Mass: 454.171

Show 6 more facts

canonical SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
chemical formula: C₂₀H₂₂N₈O₅
isomeric SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
World Health Organisation international non-proprietary name: methotrexate
Commons category: Methotrexate
defined daily dose: 2.5

Sources (8)

via Wikidata · CC0

~15 min read

Article

13 sections

Contents

Medical uses
Chemotherapy
Autoimmune disorders
Atopic dermatitis
During pregnancy
Administration
Adverse effects
Drug interactions
Vaccine interactions
Mechanism of action
History
References
External links

{{Infobox drug | Watchedfields = changed | verifiedrevid = 464193974 | image = Methotrexate skeletal.svg | image_class = skin-invert-image | width = 300 | alt = | image2 = Methotrexate-from-xtal-3D-bs-17.png | image_class2 = bg-transparent | width2 = 300 | alt2 =