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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11 entries where LYA is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	52
Chiral Atom Count	1
Bond Count	54
Aromatic Bond Count	16

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Chemical Component Summary
Name	2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID
Synonyms	LY231514
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
Formula	C₂₀ H₂₁ N₅ O₆
Molecular Weight	427.411
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C(NC(=O)c1ccc(cc1)CCc2cnc3NC(=NC(=O)c23)N)CCC(=O)O
SMILES	CACTVS	3.341	NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)c[nH]c2N1
SMILES	OpenEye OEToolkits	1.5.0	c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=O)NC(CCC(=O)O)C(=O)O
Canonical SMILES	CACTVS	3.341	NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)c[nH]c2N1
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChI	InChI	1.03	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
InChIKey	InChI	1.03	WBXPDJSOTKVWSJ-ZDUSSCGKSA-N

Drug Info: DrugBank

DrugBank ID	DB00642
Name	Pemetrexed
Groups	approved investigational
Description	Pemetrexed 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 disodium Pemetrexed monohydrate Pemetrexed disodium heptahydrate Pemetrexed ditromethamine Pemetrexed Pemetrexed disodium hemipentahydrate
Brand Names	Pemetrexed Disodium for Injection USP Pemetrexed Krka Pemetrexed Krka Page 1/1 Pemetrexed disodium Pemetrexed Hospira Pemetrexed Pfizer Pemetrexed Pemetrexed Lilly Alimta Pemetrexed Fresenius Kabi Pemetrexed for Injection, USP Armisarte Ciambra Pemetrexed Disodium for Injection Pemetrexed Medac Pemetrexed for Injection Act Pemetrexed Taro-pemetrexed Pemetrexed Baxter Pemetrexed Sandoz Pemetrexed Accord Pemrydi Rtu Pemfexy
Indication	Pemetrexed 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 Antineoplastic Agents Antineoplastic and Immunomodulating Agents Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 Substrates Drugs that are Mainly Renally Excreted Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index Enzyme Inhibitors Folic Acid Analogues Folic Acid Antagonists Glutamates Heterocyclic Compounds, Fused-Ring Immunosuppressive Agents Myelosuppressive Agents Narrow Therapeutic Index Drugs Nucleic Acid Synthesis Inhibitors OAT3/SLC22A8 Substrates OAT3/SLC22A8 Substrates with a Narrow Therapeutic Index
ATC-Code	L01BA04
CAS number	137281-23-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Thymidylate synthase	MPVAGSELPRRPLPPAAQERDAEPRPPHGELQYLGQIQHILRCGVRKDDR...	unknown	inhibitor
Bifunctional purine biosynthesis protein PURH	MAPGQLALFSVSDKTGLVEFARNLTALGLNLVASGGTAKALRDAGLAVRD...	unknown	inhibitor
Dihydrofolate reductase	MVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...	unknown	inhibitor
Trifunctional purine biosynthetic protein adenosine-3	MAARVLIIGSGGREHTLAWKLAQSHHVKQVLVAPGNAGTACSEKISNTAI...	unknown	inhibitor
Equilibrative nucleoside transporter 1	MTTSHQPQDRYKAVWLIFFMLGLGTLLPWNFFMTATQYFTNRLDMSQNVS...	unknown	inducer
Deoxycytidine kinase	MATPPKRSCPSFSASSEGTRIKKISIEGNIAAGKSTFVNILKQLCEDWEV...	unknown	inducer
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown	substrate
Folate transporter 1	MVPSSPAVEKQVPVEPGPDPELRSWRHLVCYLCFYGFMAQIRPGESFITP...	unknown	substrate
Proton-coupled folate transporter	MEGSASPPEKPRARPAAAVLCRGPVEPLVFLANFALVLQGPLTTQYLWHR...	unknown	substrate
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown
Multidrug resistance-associated protein 5	MKDIDIGKEYIIPSPGYRSVRERTSTSGTHRDREDSKFRRTRPLECQDAL...	unknown
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	substrate
Solute carrier family 22 member 11	MAFSKLLEQAGGVGLFQTLQVLTFILPCLMIPSQMLLENFSAAIPGHRCW...	unknown	substrate
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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