ESREBOXETINE

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Search structure


Synonyms	(s,s)-reboxetine Esreboxetine REBOXETINE S,s-reboxetine
Status
Molecule Category	UNKNOWN
UNII	L8S50ZY490


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

Structure


InChI Key	CBQGYUDMJHNJBX-OALUTQOASA-N
Smiles	CCOc1ccccc1O[C@@H](c1ccccc1)[C@@H]1CNCCO1
InChI	InChI=1S/C19H23NO3/c1-2-21-16-10-6-7-11-17(16)23-19(15-8-4-3-5-9-15)18-14-20-12-13-22-18/h3-11,18-20H,2,12-14H2,1H3/t18-,19-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H23NO3
Molecular Weight	313.4
AlogP	3.19
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	6.0
Polar Surface Area	39.72
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
Norepinephrine transporter inhibitor	INHIBITOR	PubMed


Protein: Norepinephrine transporter Description: Sodium-dependent noradrenaline transporter Organism : Homo sapiens P23975 ENSG00000103546

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6	-	3162	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family	-	2-3	-	0-1	-

Assay Description	Organism	Bioactivity	Reference
Inhibitory constant determined against Norepinephrine transporter	None	1.9 nM
Inhibition of norepinephrine uptake at NET in rat brain synaptosome	Rattus norvegicus	3.1 nM
Inhibition of norepinephrine uptake at human NET expressed in HEK293 cells	Homo sapiens	3.0 nM
Displacement of [3H]nisoxetine from human NET receptor expressed in HEK293 cells	Homo sapiens	1.04 nM
Displacement of [3H]citalopram from human SERT receptor expressed in HEK293 cells	Homo sapiens	661.0 nM
Antagonist activity at human 5HT3A receptor expressed in HEK293 cells assessed as inhibition of serotonin-induced inward Na+ current at >= 10 uM	Homo sapiens	50.0 %
Inhibition of [3H]norepinephrine uptake at human NET expressed in MDCK-Net6 cells by scintillation counting	Homo sapiens	3.1 nM
Inhibition of norepinephrine reuptake at NET	None	0.3 nM
Antinociceptive activity in rat assessed reduction formalin-induced hind paw acute pain at 10 mg/kg, ip	Rattus norvegicus	33.0 %
Inhibition of human recombinant NET expressed in HEK293 cells assessed as inhibition of [3H]NE reuptake	Homo sapiens	1.995 nM

Related Entries

Cross References

Resources	Reference
ChEBI	125535
ChEMBL	CHEMBL180101
DrugBank	DB12395
FDA SRS	L8S50ZY490
Human Metabolome Database	HMDB0014379
Guide to Pharmacology	4808
PharmGKB	PA144614921
PubChem	65856
SureChEMBL	SCHEMBL34534
ZINC	ZINC000000006923

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).