pralatrexate   Click here for help

GtoPdb Ligand ID: 6840

Synonyms: Folotyn® | PDX
Approved drug
pralatrexate is an approved drug (FDA (2009))
Compound class: Synthetic organic
Comment: Inhibits dihydrofolate reductase, GAR transformylase and thymidylate synthase. The INN document specifies that pralatrexate is a racemic mixture of two epimers. These epimers are represented by the PubChem entries CID 23230419 and CID 11155808. We do not specify stereochemistry at the carbon atom which determines the two epimers, therefore our image represents the mixture.

SARS-CoV-2 and COVID-19: Pralatrexate has been identified as an inhibitor of the viral RNA-dependent RNA polymerase (RdRp; nsp12) from SARS-CoV-2 [2]. This translates to inhibition of SARS-CoV-2 replication in vitro (EC50 8 nM). Structural anaylsis suggests that the interaction points between pralatrexate and RdRp are distinct from those between remdesivir and RdRp.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 207.3
Molecular weight 477.18
XLogP -2.16
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES C#CCC(c1ccc(cc1)C(=O)NC(C(=O)O)CCC(=O)O)Cc1cnc2c(n1)c(N)nc(n2)N
Isomeric SMILES C#CCC(c1ccc(cc1)C(=O)N[C@H](C(=O)O)CCC(=O)O)Cc1cnc2c(n1)c(N)nc(n2)N
InChI InChI=1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
InChI Key OGSBUKJUDHAQEA-WMCAAGNKSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2009))
IUPAC Name Click here for help
(2S)-2-[[4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl]amino]pentanedioic acid
International Nonproprietary Names Click here for help
INN number INN
8560 pralatrexate
Synonyms Click here for help
Folotyn® | PDX
Database Links Click here for help
CAS Registry No. 146464-95-1
ChEMBL Ligand CHEMBL1201746
DrugBank Ligand DB06813
DrugCentral Ligand 4117
GtoPdb PubChem SID 178103446
PubChem CID 148121
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Wikipedia Pralatrexate