CHEBI:63722 - pemetrexed disodium

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ChEBI Name pemetrexed disodium
ChEBI ID CHEBI:63722
Definition An organic sodium salt that is the disodium salt of N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H19N5Na2O6
Net Charge 0
Average Mass 471.37430
Monoisotopic Mass 471.11307
InChI InChI=1S/C20H21N5O6.2Na/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);;/q;2*+1/p-2/t13-;;/m0../s1
InChIKey NYDXNILOWQXUOF-GXKRWWSZSA-L
SMILES [Na+].[Na+].Nc1nc(=O)c2c(CCc3ccc(cc3)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)c[nH]c2[nH]1
Roles Classification
Biological Role(s): antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3).
EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor
An EC 2.1.2.* (hydroxymethyl-, formyl- and related transferases) inhibitor that interferes with the action of phosphoribosylglycinamide formyltransferase (EC 2.1.2.2).
EC 2.1.1.45 (thymidylate synthase) inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of thymidylate synthase (EC 2.1.1.45).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pemetrexed disodium (CHEBI:63722) has part pemetrexed(2−) (CHEBI:63724)
pemetrexed disodium (CHEBI:63722) has role antimetabolite (CHEBI:35221)
pemetrexed disodium (CHEBI:63722) has role antineoplastic agent (CHEBI:35610)
pemetrexed disodium (CHEBI:63722) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683)
pemetrexed disodium (CHEBI:63722) has role EC 2.1.1.45 (thymidylate synthase) inhibitor (CHEBI:63720)
pemetrexed disodium (CHEBI:63722) has role EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor (CHEBI:63721)
pemetrexed disodium (CHEBI:63722) is a organic sodium salt (CHEBI:38700)
Incoming pemetrexed disodium heptahydrate (CHEBI:63723) has part pemetrexed disodium (CHEBI:63722)
IUPAC Name
disodium N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate
Synonym Source
disodium (2S)-2-({4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}amino)pentanedioate IUPAC
Manual Xrefs Databases
CN101411710 Patent
CN101560206 Patent
D03828 KEGG DRUG
DB00642 DrugBank
EP2301909 Patent
EP2334685 Patent
US2009181990 Patent
US2011124861 Patent
US2011196154 Patent
WO2010028105 Patent
WO2011019986 Patent
WO2011064256 Patent
View more database links
Registry Numbers Types Sources
150399-23-8 CAS Registry Number ChemIDplus
150399-23-8 CAS Registry Number KEGG DRUG
8964395 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19137122 PubMed citation Europe PMC
20209614 PubMed citation Europe PMC
Last Modified
23 January 2012