pemetrexed   Click here for help

GtoPdb Ligand ID: 6837

Synonyms: Alimta® | LY-231514
Approved drug
pemetrexed is an approved drug (FDA (2004), EMA (2009))
Compound class: Synthetic organic
Comment: Inhibits dihydrofolate reductase, GAR transformylase and thymidylate synthase.
Marketed formulations may contain pemetrexed disodium (PubChem CID 46931002).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 10
Topological polar surface area 191.26
Molecular weight 427.15
XLogP 0.49
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)CCC(C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N
Isomeric SMILES OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N
InChI InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m1/s1
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Summary of Clinical Use Click here for help
Used to treat pleural mesothelioma and non-small cell lung cancer.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Inhibition of the enzymatic activity of thymidylate synthase reduces the synthesis of precursor pyrimidine nucleotides. This prevents the formation of DNA and RNA and subsequently results in cell death.
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