NAFTOPIDIL

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII R9PHW59SFN
EPA CompTox DTXSID5045176

Structure

InChI Key HRRBJVNMSRJFHQ-UHFFFAOYSA-N
Smiles COc1ccccc1N1CCN(CC(O)COc2cccc3ccccc23)CC1
InChI
InChI=1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H28N2O3
Molecular Weight 392.5
AlogP 3.41
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 45.17
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Alpha-1d adrenergic receptor antagonist ANTAGONIST PubMed PubMed
Protein: Alpha-1d adrenergic receptor
Description: Alpha-1D adrenergic receptor
Organism : Homo sapiens
P25100 ENSG00000171873
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 55-55 12-143 4-6 -
Assay Description Organism Bioactivity Reference
Alpha-1 adrenergic receptor binding affinity by measuring the displacement of [3H]prazosin binding in rat brain None 39.0 nM
Binding constant measured against Alpha-1A adrenergic receptor in human prostate; ++:moderately active Homo sapiens 3.7 nM
Binding affinity to adrenergic alpha1A receptor (unknown origin) Homo sapiens 5.888 nM Binding affinity to adrenergic alpha1A receptor (unknown origin) Homo sapiens 5.88 nM
Antagonist activity at Sprague-Dawley rat prostatic vas deferens adrenergic alpha-1A receptor after 20 mins Rattus norvegicus 33.11 nM
Antagonist activity at Sprague-Dawley rat spleen adrenergic alpha-1B receptor after 20 mins Rattus norvegicus 177.83 nM
Antagonist activity at Sprague-Dawley rat thoracic aorta adrenergic alpha-1D receptor after 20 mins Rattus norvegicus 11.75 nM
Antagonist activity at adrenergic alpha1A receptor (unknown origin) by firefly and renilla dual glo luciferase assay Homo sapiens 555.0 nM
Antagonist activity at adrenergic alpha1B receptor (unknown origin) by firefly and renilla dual glo luciferase assay Homo sapiens 634.0 nM
Antagonist activity at adrenergic alpha1D receptor (unknown origin) by firefly and renilla dual glo luciferase assay Homo sapiens 55.2 nM
Antagonist activity at alpha1A-adrenoreceptor in Sprague-Dawley rat vas deferens assessed as relaxation of (-)-noradrenaline-induced contractile response Rattus norvegicus 33.11 nM
Antagonist activity at alpha1B-adrenoreceptor in Sprague-Dawley rat spleen assessed as relaxation of (-)-noradrenaline-induced contractile response Rattus norvegicus 177.83 nM
Antagonist activity at alpha1D-adrenoreceptor in Sprague-Dawley rat thoracic aorta assessed as relaxation of (-)-noradrenaline-induced contractile response Rattus norvegicus 11.75 nM
Displacement of [125I-HEAT from human alpha1A-adrenoreceptor expressed in CHOK1 cell membranes incubated for 60 mins Homo sapiens 3.715 nM
Displacement of [125I-HEAT from human alpha1B-adrenoreceptor expressed in CHOK1 cell membranes incubated for 60 mins Homo sapiens 19.95 nM
Displacement of [125I-HEAT from human alpha1D-adrenoreceptor expressed in CHOK1 cell membranes incubated for 60 mins Homo sapiens 1.202 nM
Antagonist activity at alpha 1A adrenergic receptor (unknown origin) by luciferase reporter gene assay Homo sapiens 555.0 nM
Antagonist activity at alpha 1B adrenergic receptor (unknown origin) by luciferase reporter gene assay Homo sapiens 634.0 nM
Antagonist activity at alpha 1D adrenergic receptor (unknown origin) by luciferase reporter gene assay Homo sapiens 55.2 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 4.28 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 7.29 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae -0.32 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 8.59 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 5.99 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.55 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 1.21 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 90.58 %
Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as inhibition of noradrenaline-induced contractions at 10 uM relative to untreated control Rattus norvegicus 47.53 %
Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as inhibition of noradrenaline-induced contractions at 100 uM relative to untreated control Rattus norvegicus 65.15 %
Antagonist activity at alpha-1D adrenergic receptor in SPF rat vas thoracic aorta assessed as inhibition of noradrenaline-induced contractions Rattus norvegicus 143.22 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.68 %
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 0.14 % 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 0.14 %

Cross References

Resources Reference
ChEBI 31891
ChEMBL CHEMBL142635
DrugBank DB12092
DrugCentral 1873
FDA SRS R9PHW59SFN
PubChem 4418
SureChEMBL SCHEMBL113215
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