methotrexate   Click here for help

GtoPdb Ligand ID: 4815

Synonyms: Abitrexate® | amethopterin | Nordimet® | Rasuvo®
Approved drug PDB Ligand Immunopharmacology Ligand
methotrexate is an approved drug (FDA (1953), EMA (2016))
Compound class: Synthetic organic
Comment: 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.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 210.54
Molecular weight 454.17
XLogP -2.67
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)CCC(C(=O)O)NC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C
Isomeric SMILES OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1953), EMA (2016))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid
International Nonproprietary Names Click here for help
INN number INN
926 methotrexate
Synonyms Click here for help
Abitrexate® | amethopterin | Nordimet® | Rasuvo®
Database Links Click here for help
CAS Registry No. 59-05-2 (source: Scifinder)
ChEMBL Ligand CHEMBL34259
DrugBank Ligand DB00563
DrugCentral Ligand 1751
GtoPdb PubChem SID 178101517
Immunopaedia Search methotrexate
PubChem CID 126941
Search Google for chemical match using the InChIKey FBOZXECLQNJBKD-ZDUSSCGKSA-N
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SynPHARM 79522 (in complex with dihydrofolate reductase)
UniChem Compound Search for chemical match using the InChIKey FBOZXECLQNJBKD-ZDUSSCGKSA-N
UniChem Connectivity Search for chemical match using the InChIKey FBOZXECLQNJBKD-ZDUSSCGKSA-N
Wikipedia Methotrexate

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Methotrexate (links to external site)
Cat. No. 1230