Drug Details

General Information of the Drug (ID: DR8475)
Name
Pemetrexed
Synonyms
Pemetrexed; 137281-23-3; Pemetrexed disodium; Alimta; LY231514; UNII-04Q9AIZ7NO; Pemetrexed acid; CHEBI:63616; 04Q9AIZ7NO; LY-231514; (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid; N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid; C20H21N5O6; 137281-23-3 (free acid); LY 231514; NSC-698037; LY-2315; N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid; Alimta (TN); (S)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid; 2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID; N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid; (4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoyl)-L-glutamic acid; (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo-[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid; LYA; N-[4-[2(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid; Pemetrexed [INN:BAN]; HSDB 7316; 1juj; Pemetrexed (TN); N-(4-[2-(2-amino-4,7-Dihydro-4-Oxo-1H-Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl)-L-Glutamic Acid; Pemetrexed (INN); Alimta (TN) (Lilly); SCHEMBL7968; US9422297, Pemetrexed; N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimdin-5-yl)ethyl)benzoyl)glutamic acid; CHEMBL225072; DTXSID2048329; Premetrexed [Common mis-spelling]; ZINC1540998; BDBM50027656; CP0119; NSC698037; s5971; AKOS015896253; AKOS016842348; AC-1701; CS-1297; DB00642; NCGC00166414-11; NCGC00167517-01; NCGC00242485-01; AS-30680; HY-10820; L-Glutamic acid, N-(4-(2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-; DB-024764; P2288; A12668; D07472; S-4927; 41413-EP2270012A1; 41413-EP2270013A1; 41413-EP2305681A1; 41413-EP2311838A1; 41421-EP2270012A1; 41421-EP2270013A1; 41421-EP2305681A1; 41421-EP2311838A1; 89077-EP2270012A1; 89077-EP2270013A1; 89077-EP2305681A1; AB01273937-01; 281P233; Q415220; J-502393; L-Glutamic acid,3-d]pyrimidin-5-yl]ethyl]benzoyl]-; 1006872-74-7; N-({4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]phenyl}carbonyl)-L-glutamic acid; N-[4-[2(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid; N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7h-pyrrolo[2,3-d]pyrimi-din-5-yl)ethyl]benzoyl]l-glutamic acid; N-[4-[2-[2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]ethyl]benzoyl]glutamic acid
    Click to Show/Hide
Molecular Type
Small molecule
Disease Pleural mesothelioma [ICD-11: 2C26] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C20H21N5O6
PubChem CID
135410875
Canonical SMILES
C1=CC(=CC=C1CCC2=CNC3=C2C(=O)NC(=N3)N)C(=O)NC(CCC(=O)O)C(=O)O
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
InChIKey
WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
CAS Number
CAS 137281-23-3
ChEBI ID
CHEBI:63616
TTD Drug ID
D0Y4GO
DrugBank ID
DB00642
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Metformin      Galega officinalis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H1975 CVCL_1511 Lung adenocarcinoma Homo sapiens
HCC827 CVCL_2063 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Metformin synergistic pemetrexed suppresses non-small-cell lung cancer cell proliferation and invasion in vitro.
Target and Pathway
Target(s) Candida thymidylate synthase (Candi TMP1)  Molecule Info  [3]
BioCyc Pyrimidine deoxyribonucleotides biosynthesis from CTP Click to Show/Hide
2 Pyrimidine deoxyribonucleotides de novo biosynthesis
3 Superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis
4 Superpathway of pyrimidine deoxyribonucleoside salvage
5 DTMP de novo biosynthesis (mitochondrial)
6 Pyrimidine deoxyribonucleosides salvage
KEGG Pathway Pyrimidine metabolism Click to Show/Hide
2 One carbon pool by folate
3 Metabolic pathways
Panther Pathway De novo pyrimidine deoxyribonucleotide biosynthesis Click to Show/Hide
2 Formyltetrahydroformate biosynthesis
Pathwhiz Pathway Pyrimidine Metabolism Click to Show/Hide
Pathway Interaction Database E2F transcription factor network Click to Show/Hide
Reactome E2F mediated regulation of DNA replication Click to Show/Hide
2 Pyrimidine biosynthesis
3 G1/S-Specific Transcription
WikiPathways Trans-sulfuration and one carbon metabolism Click to Show/Hide
2 Retinoblastoma (RB) in Cancer
3 One Carbon Metabolism
4 Integrated Pancreatic Cancer Pathway
5 miR-targeted genes in muscle cell - TarBase
6 miR-targeted genes in lymphocytes - TarBase
7 miR-targeted genes in leukocytes - TarBase
8 miR-targeted genes in epithelium - TarBase
9 Metabolism of nucleotides
10 Fluoropyrimidine Activity
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6837).
Reference 2 Metformin synergistic pemetrexed suppresses non-small-cell lung cancer cell proliferation and invasion in vitro. Cancer Med. 2017 Aug;6(8):1965-1975.
Reference 3 Updated clinical information on multitargeted antifolates in lung cancer. Clin Lung Cancer. 2009 Mar;10 Suppl 1:S35-40.
 Download Picture         KEGG Link      
 Download Picture         KEGG Link