Structure via PubChem · Public domain (PubChem)
methotrexate
Sign in to saveAlso 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.
OverviewAI-generated
Methotrexate is a chemical compound with the formula C₂₀H₂₂N₈O₅. Its IUPAC name is (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid. The substance has a mass of 454.171 and a weight of 454.4. It possesses a charge of 0, an xlogp of -1.8, and a topological polar surface area of 211. The molecule contains five hydrogen bond donors and twelve hydrogen bond acceptors.
The defined daily dose for methotrexate is 2.5. In scientific literature, the term is associated with 66,595 records. The compound is referenced by 1,276 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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 Ų
- 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
~15 min read
Encyclopedic overview
13 sectionsContents
- 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 =
| pronounce = | tradename = Trexall, Rheumatrex, Otrexup, others | Drugs.com = | MedlinePlus = a682019 | DailyMedID = Methotrexate | pregnancy_AU = D | routes_of_administration = By mouth, intravenous, intramuscular, subcutaneous, intrathecal | ATC_prefix = L01 | ATC_suffix = BA01 | ATC_supplemental =
Excerpted from Wikipedia’s “methotrexate” article, available under the CC BY-SA 4.0 licence.