SILODOSIN

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Search structure


Trade Names	RAPAFLO SILODOSIN
Synonyms	KAD-3213 KMD-3213 Kso-0400 Rapaflo Rapilif Silodal Silodosin Silodyx Urief Urorec
Status
Molecule Category	UNKNOWN
ATC	G04CA04
UNII	CUZ39LUY82
EPA CompTox	DTXSID40167045


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

Structure


InChI Key	PNCPYILNMDWPEY-QGZVFWFLSA-N
Smiles	C[C@H](Cc1cc2c(c(C(N)=O)c1)N(CCCO)CC2)NCCOc1ccccc1OCC(F)(F)F
InChI	InChI=1S/C25H32F3N3O4/c1-17(30-8-12-34-21-5-2-3-6-22(21)35-16-25(26,27)28)13-18-14-19-7-10-31(9-4-11-32)23(19)20(15-18)24(29)33/h2-3,5-6,14-15,17,30,32H,4,7-13,16H2,1H3,(H2,29,33)/t17-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C25H32F3N3O4
Molecular Weight	495.54
AlogP	3.07
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	13.0
Polar Surface Area	97.05
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	35.0

Bioactivity

Mechanism of Action	Action	Reference
Alpha-1a adrenergic receptor antagonist	ANTAGONIST	DailyMed


Protein: Alpha-1a adrenergic receptor Description: Alpha-1A adrenergic receptor Organism : Homo sapiens P35348 ENSG00000120907

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	7943-25119	-	-	-
Ion channel Voltage-gated ion channel Voltage-gated sodium channel	-	63096	-	-	-
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor	-	116-541	-	0-0	100

Assay Description	Organism	Bioactivity	Reference
Binding affinity was tested on human Alpha-1D adrenergic receptor	None	1.995 nM
Binding affinity was tested on human Alpha-1A adrenergic receptor	None	0.03981 nM
Binding affinity was tested on human Alpha-1B adrenergic receptor	None	19.95 nM
Binding constant measured against Alpha-1A adrenergic receptor in human prostate; +++:highly active	Homo sapiens	0.036 nM
Antagonist activity at human alpha-1A adrenergic receptor transfected in HEK293 cells assessed as reduction in agonist-induced calcium mobilization after 10 mins	Homo sapiens	1.9 nM
Antagonist activity at human alpha-1B adrenergic receptor transfected in HEK293 cells assessed as reduction in agonist-induced calcium mobilization after 10 mins	Homo sapiens	541.4 nM
Antagonist activity at alpha-1D adrenergic receptor (unknown origin) transfected in HEK293 cells assessed as reduction in agonist-induced calcium mobilization after 10 mins	Homo sapiens	27.3 nM
Inhibition of noradrenaline-induced contraction of Sprague-Dawley rat urethra smooth muscles after 20 mins	Rattus norvegicus	17.3 nM
Inhibition of noradrenaline-induced contraction of Sprague-Dawley rat aorta after 20 mins	Rattus norvegicus	26.6 nM
Antagonist activity at human full-length N-terminal SNAP-tagged alpha1A adrenoceptor expressed in HEK293 cells assessed as inhibition of agonist-induced calcium mobilization preincubated for 10 mins followed by agonist addition by fluo-4 AM dye-based assay	Homo sapiens	1.8 nM
Antagonist activity at human full-length N-terminal SNAP-tagged alpha1A adrenoceptor expressed in HEK293 cells assessed as inhibition of agonist-induced calcium mobilization at 10 uM preincubated for 10 mins followed by agonist addition by fluo-4 AM dye-based assay relative to control	Homo sapiens	100.0 %
Antagonist activity at human full-length N-terminal SNAP-tagged alpha1B adrenoceptor expressed in HEK293 cells assessed as inhibition of agonist-induced calcium mobilization preincubated for 10 mins followed by agonist addition by fluo-4 AM dye-based assay	Homo sapiens	116.0 nM
Antagonist activity at human full-length N-terminal SNAP-tagged alpha1D adrenoceptor expressed in HEK293 cells assessed as inhibition of agonist-induced calcium mobilization preincubated for 10 mins followed by agonist addition by fluo-4 AM dye-based assay	Homo sapiens	6.3 nM
Antagonist activity at alpha1A adrenoceptor in Sprague-Dawley rat urethra assessed as inhibition of norepinephrine-induced smooth muscle contraction after 20 mins	Rattus norvegicus	0.8 nM
Antagonist activity at alpha1B adrenoceptor in Sprague-Dawley rat aorta assessed as inhibition of norepinephrine-induced smooth muscle contraction after 20 mins	Rattus norvegicus	90.1 nM
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	-9.07 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.0 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	1.021 %
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	-0.02 %		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	-0.02 %		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	135929
ChEMBL	CHEMBL24778
DrugBank	DB06207
DrugCentral	4151
FDA SRS	CUZ39LUY82
Guide to Pharmacology	493
KEGG	D01965
PubChem	5312125
SureChEMBL	SCHEMBL136973
ZINC	ZINC000003806063

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).