DAROLUTAMIDE

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Search structure


Trade Names	NUBEQA
Synonyms	BAY 1841788 BAY-1841788 BAY1841788 Darolutamide Nubeqa ODM-201 Odm-201
Status
Molecule Category	UNKNOWN
ATC	L02BB06
UNII	X05U0N2RCO


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

Structure


InChI Key	BLIJXOOIHRSQRB-PXYINDEMSA-N
Smiles	CC(O)c1cc(C(=O)N[C@@H](C)Cn2ccc(-c3ccc(C#N)c(Cl)c3)n2)n[nH]1
InChI	InChI=1S/C19H19ClN6O2/c1-11(22-19(28)18-8-17(12(2)27)23-24-18)10-26-6-5-16(25-26)13-3-4-14(9-21)15(20)7-13/h3-8,11-12,27H,10H2,1-2H3,(H,22,28)(H,23,24)/t11-,12?/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H19ClN6O2
Molecular Weight	398.85
AlogP	2.67
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	6.0
Polar Surface Area	119.62
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	28.0

Bioactivity

Mechanism of Action	Action	Reference
Androgen Receptor antagonist	ANTAGONIST	PubMed Other


Protein: Androgen Receptor Description: Androgen receptor Organism : Homo sapiens P10275 ENSG00000169083

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4	-	26	-	11	-

Assay Description	Organism	Bioactivity	Reference
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	-10.61 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	3.453 %
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	-0.11 %		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	-0.11 %
Inhibition of androgen receptor (unknown origin)	Homo sapiens	11.0 nM		Inhibition of androgen receptor (unknown origin)	Homo sapiens	26.0 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL4297185
DrugBank	DB12941
FDA SRS	X05U0N2RCO
Guide to Pharmacology	10439
PubChem	67171867
SureChEMBL	SCHEMBL1814935

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).