LYA

2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID

Created: 2001-08-24
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count52
Chiral Atom Count1
Bond Count54
Aromatic Bond Count16
2D diagram of LYA
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Chemical Component Summary

Name2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID
SynonymsLY231514
Systematic Name (OpenEye OEToolkits)(2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[4,5-e]pyrimidin-5-yl)ethyl]phenyl]carbonylamino]pentanedioic acid
FormulaC20 H21 N5 O6
Molecular Weight427.411
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)C(NC(=O)c1ccc(cc1)CCc2cnc3NC(=NC(=O)c23)N)CCC(=O)O
SMILESCACTVS3.341NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)c[nH]c2N1
SMILESOpenEye OEToolkits1.5.0c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=O)NC(CCC(=O)O)C(=O)O
Canonical SMILESCACTVS3.341 NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)c[nH]c2N1
Canonical SMILESOpenEye OEToolkits1.5.0 c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChIInChI1.03 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-/m0/s1
InChIKeyInChI1.03 WBXPDJSOTKVWSJ-ZDUSSCGKSA-N

Drug Info: DrugBank

DrugBank IDDB00642 
NamePemetrexed
Groups
  • approved
  • investigational
DescriptionPemetrexed is a chemotherapy drug that is manufactured and marketed by Eli Lilly and Company under the brand name Alimta. It is indicated for use in combination with cisplatin for the treatment of patients with malignant pleural mesothelioma whose disease is either unresectable or who are otherwise not candidates for curative surgery. Its use in non-small cell lung cancer has also been investigated. Pemetrexed was first approved by the FDA in February 4, 2004.[A253907]
Synonyms
  • Pemetrexed
  • Pemetrexed disodium
  • Pemetrexed disodium hemipentahydrate
  • Pemetrexed ditromethamine
  • Pemetrexed disodium heptahydrate
Brand Names
  • Act Pemetrexed
  • Pemetrexed Sandoz
  • Ciambra
  • Pemetrexed Accord
  • Pemetrexed Hospira
IndicationPemetrexed is indicated for the treatment of the following conditions: **Non-squamous non-small cell lung cancer (NSCLC)** - in combination with [pembrolizumab] and platinum-based chemotherapy as initial treatment in metastatic disease where no EGFR or ALK genomic tumour aberrations exist [L40943] - in combination with [cisplatin] as initial treatment for locally advanced or metastatic disease [L40943,L44883] - as maintenance treatment for locally advanced or metastatic disease that has not progressed following four cycles of platinum-based chemotherapy [L40943,L44883] - recurrent metastatic disease following prior chemotherapy [L40943] - as monotherapy for the second-line treatment of patients with locally advanced or metastatic non-squamous non-small cell lung cancer [L44883] **Malignant pleural mesothelioma** - in combination with [cisplatin] for the initial treatment of patients with malignant pleural mesothelioma.[L40943,L44883] In the US, it is reserved for patients whose disease is unresectable or otherwise not candidates for curative surgery.[L40943]
Categories
  • Amino Acids
  • Amino Acids, Acidic
  • Amino Acids, Dicarboxylic
  • Amino Acids, Peptides, and Proteins
  • Antimetabolites
ATC-CodeL01BA04
CAS number137281-23-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Thymidylate synthaseMPVAGSELPRRPLPPAAQERDAEPRPPHGELQYLGQIQHILRCGVRKDDR...unknowninhibitor
Bifunctional purine biosynthesis protein PURHMAPGQLALFSVSDKTGLVEFARNLTALGLNLVASGGTAKALRDAGLAVRD...unknowninhibitor
Dihydrofolate reductaseMVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...unknowninhibitor
Trifunctional purine biosynthetic protein adenosine-3MAARVLIIGSGGREHTLAWKLAQSHHVKQVLVAPGNAGTACSEKISNTAI...unknowninhibitor
Equilibrative nucleoside transporter 1MTTSHQPQDRYKAVWLIFFMLGLGTLLPWNFFMTATQYFTNRLDMSQNVS...unknowninducer
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL225072
PubChem 5288715, 135410875, 446556
ChEMBL CHEMBL225072
ChEBI CHEBI:63616