methotrexate

Ligand id: 4815

Name: methotrexate

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Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 13
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 210.54
Molecular weight 454.17
XLogP -2.58
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1953))
IUPAC Name
(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid
International Nonproprietary Names
INN number INN
926 methotrexate
Synonyms
Abitrexate® | amethopterin | Rasuvo®
Comments
Methotrexate is a folate (folic acid) analogue that is classified as an antimetabolite and antifolate drug, and a disease-modifying anti-rheumatic drug (DMARD). It is used clinically for its antiproliferative and anti-inflammatory effects. The primary action of methotrexate is inhibition of the enzyme dihydrofolate reductase (DHFR). DHFR is essential for the production of precursors that are required for de novo purine synthesis.
Methotrexate is on the World Health Organisation's List of Essential Medicines (link to WHO 20th Essential Medicines List (2017)).
Database Links
CAS Registry No. 59-05-2 (source: Scifinder)
ChEBI CHEBI:44185
ChEMBL Ligand CHEMBL34259
DrugBank Ligand DB00563
GtoPdb PubChem SID 178101517
PubChem CID 126941
RCSB PDB Ligand MTX
Search Google for chemical match using the InChIKey FBOZXECLQNJBKD-ZDUSSCGKSA-N
Search Google for chemicals with the same backbone FBOZXECLQNJBKD
Search PubMed clinical trials methotrexate
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Search PubMed titles/abstracts methotrexate
Search UniChem for chemical match using the InChIKey FBOZXECLQNJBKD-ZDUSSCGKSA-N
Search UniChem for chemicals with the same backbone FBOZXECLQNJBKD
SynPHARM 79522 (in complex with dihydrofolate reductase)
Wikipedia Methotrexate

Product suppliers

Tocris
Methotrexate
Cat. No. 1230