Chemicals and Drugs

Methotrexate

An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of TETRAHYDROFOLATE DEHYDROGENASE and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of TETRAHYDROFOLATE DEHYDROGENASE and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA.

Chemical Identity

Chemical Information

Molecular Formula
C20H22N8O5
Molecular Weight
454.4 g/mol
CAS Registry No.
59-05-2
IUPAC Name
(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
InChIKey
FBOZXECLQNJBKD-ZDUSSCGKSA-N
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
MeSH Unique ID
D008727
Source
PubChem CID 126941

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

12 entry terms
  • Amethopterin
  • Methotrexate Hydrate
  • Methotrexate Sodium
  • Methotrexate, (D)-Isomer
  • Methotrexate, (DL)-Isomer
  • Methotrexate, Dicesium Salt
  • Methotrexate, Disodium Salt
  • Methotrexate, Sodium Salt
  • Mexate
  • Dicesium Salt Methotrexate
  • Hydrate, Methotrexate
  • Sodium, Methotrexate

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Hierarchy

Tree Number

  1. D03w.633.100.733.631.192w.500w

MeSH Record

NLM Classification

QV 269

AMA Style

References

  1. National Library of Medicine. Methotrexate. Medical Subject Headings (MeSH). 2026. Unique ID D008727. http://id.nlm.nih.gov/mesh/2026/D008727
  2. Methotrexate. In: Wikipedia. https://en.wikipedia.org/wiki/Methotrexate
  3. Methotrexate. In: Wikidata. https://www.wikidata.org/wiki/Q422232
  4. Methotrexate. In: PubChem Compound. CID 126941. https://pubchem.ncbi.nlm.nih.gov/compound/126941