ORPHENADRINE CITRATE


Trade Names	NORFLEX ORPHENADRINE CITRATE
Synonyms	NSC-757238 Norflex Orphenadine citrate Orphenadrine (citrate) Orphenadrine Citrate Orphenadrine citrate Orphenadrine dihydrogen citrate
Status
Molecule Category	Salt-form
UNII	X0A40N8I4S
EPA CompTox	DTXSID8044678
Parent Compound:	ORPHENADRINE


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

Structure


InChI Key	MMMNTDFSPSQXJP-UHFFFAOYSA-N
Smiles	Cc1ccccc1C(OCCN(C)C)c1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O
InChI	InChI=1S/C18H23NO.C6H8O7/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-12,18H,13-14H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C24H31NO8
Molecular Weight	461.51
AlogP	3.66
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	6.0
Polar Surface Area	12.47
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	20.0

Bioactivity

Mechanism of Action	Action	Reference
Glutamate [NMDA] receptor antagonist	ANTAGONIST	PubMed PubMed PubMed


Protein: Glutamate [NMDA] receptor Description: Glutamate receptor ionotropic, NMDA 2D Organism : Homo sapiens O15399 ENSG00000105464











Protein: Glutamate [NMDA] receptor Description: Glutamate receptor ionotropic, NMDA 3B Organism : Homo sapiens O60391 ENSG00000116032










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











Protein: Histamine H1 receptor Description: Histamine H1 receptor Organism : Homo sapiens P35367 ENSG00000196639











Protein: Sodium channel alpha subunit Description: Sodium channel protein type 1 subunit alpha Organism : Homo sapiens P35498 ENSG00000144285










Protein: Sodium channel alpha subunit Description: Sodium channel protein type 4 subunit alpha Organism : Homo sapiens P35499 ENSG00000007314











Protein: Glutamate [NMDA] receptor Description: Glutamate receptor ionotropic, NMDA 1 Organism : Homo sapiens Q05586 ENSG00000176884












Protein: Glutamate [NMDA] receptor Description: Glutamate receptor ionotropic, NMDA 2A Organism : Homo sapiens Q12879 ENSG00000183454










Protein: Glutamate [NMDA] receptor Description: Glutamate receptor ionotropic, NMDA 2B Organism : Homo sapiens Q13224 ENSG00000273079











Protein: Sodium channel alpha subunit Description: Sodium channel protein type 5 subunit alpha Organism : Homo sapiens Q14524 ENSG00000183873








Protein: Glutamate [NMDA] receptor Description: Glutamate receptor ionotropic, NMDA 2C Organism : Homo sapiens Q14957 ENSG00000161509











Protein: Sodium channel alpha subunit Description: Sodium channel protein type 9 subunit alpha Organism : Homo sapiens Q15858 ENSG00000169432







Protein: Glutamate [NMDA] receptor Description: Glutamate receptor ionotropic, NMDA 3A Organism : Homo sapiens Q8TCU5 ENSG00000198785











Protein: Sodium channel alpha subunit Description: Sodium channel protein type 2 subunit alpha Organism : Homo sapiens Q99250 ENSG00000136531










Protein: Sodium channel alpha subunit Description: Sodium channel protein type 3 subunit alpha Organism : Homo sapiens Q9NY46 ENSG00000153253









Protein: Sodium channel alpha subunit Description: Sodium channel protein type 11 subunit alpha Organism : Homo sapiens Q9UI33 ENSG00000168356







Protein: Sodium channel alpha subunit Description: Sodium channel protein type 8 subunit alpha Organism : Homo sapiens Q9UQD0 ENSG00000196876











Protein: Sodium channel alpha subunit Description: Sodium channel protein type 10 subunit alpha Organism : Homo sapiens Q9Y5Y9 ENSG00000185313

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	88

Assay Description	Organism	Bioactivity
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	87.55 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	96.44 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	7.93 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.03 %	Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.03 %

Cross References

Resources	Reference
ChEBI	7790
ChEMBL	CHEMBL1200395
FDA SRS	X0A40N8I4S
PubChem	83823
SureChEMBL	SCHEMBL119470

CONTENTS