FLUPIRTINE


Synonyms	Flupirtine Flupirtinte W-2964
Status
Molecule Category	UNKNOWN
ATC	N02BG07
UNII	MOH3ET196H
EPA CompTox	DTXSID4048436


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	JUUFBMODXQKSTD-UHFFFAOYSA-N
Smiles	CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)nc1N
InChI	InChI=1S/C15H17FN4O2/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C15H17FN4O2
Molecular Weight	304.32
AlogP	2.98
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	5.0
Polar Surface Area	89.27
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	22.0

Assay Description	Organism	Bioactivity
Inhibition of human FAAH at 1 uM	Homo sapiens	8.4 %
Agonist activity at human KCNQ2/3 expressed in HEK293 cells by FLIPR based thallium influx assay	Homo sapiens	560.0 nM
Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli BLR(DE3) assessed as reduction in NADPH level using L-serine, THF and NADP+ at 6.5 or 26.5 uM incubated for 5 mins by SHMT2-MTHFD coupled reaction based fluorescence assay relative to control	Homo sapiens	86.1 %
Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli BLR(DE3) assessed as reduction in NADPH level using L-serine, THF and NADP+ incubated for 5 mins by SHMT2-MTHFD coupled reaction based fluorescence assay	Homo sapiens	933.25 nM

Cross References

Resources	Reference
ChEBI	94646
ChEMBL	CHEMBL255044
DrugBank	DB06623
DrugCentral	1215
FDA SRS	MOH3ET196H
Guide to Pharmacology	2598
PharmGKB	PA166152829
PubChem	53276
SureChEMBL	SCHEMBL25009
ZINC	ZINC000000001473

CONTENTS


PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains. Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).