ABIRATERONE ACETATE

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Trade Names	ABIRATERONE ACETATE YONSA ZYTIGA
Synonyms	Abiraterone acetate CB-7630 CB7630 NSC-748121 NSC-749227 Yonsa Zytiga
Status
Molecule Category	Free-form
UNII	EM5OCB9YJ6
EPA CompTox	DTXSID3049043
Parent Compound:	ABIRATERONE


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

Structure


InChI Key	UVIQSJCZCSLXRZ-UBUQANBQSA-N
Smiles	CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(c4cccnc4)=CC[C@@H]32)C1
InChI	InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H33NO2
Molecular Weight	391.56
AlogP	5.97
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	2.0
Polar Surface Area	39.19
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	29.0

Bioactivity

Mechanism of Action	Action	Reference
Cytochrome P450 17A1 inhibitor	INHIBITOR	FDA


Protein: Cytochrome P450 17A1 Description: Steroid 17-alpha-hydroxylase/17,20 lyase Organism : Homo sapiens P05093 ENSG00000148795

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 17 Cytochrome P450 family 17A Cytochrome P450 17A1	-	17-18	-	-	-
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	17050	-	-	-	-

Assay Description	Organism	Bioactivity	Reference
Ability to inhibit the C17,20-lyase enzyme by 50% using 17-alpha-hydroxyprogesterone as substrate.	None	17.0 nM
Ability to inhibit the Steroid 17-alpha-hydroxylase/17,20 lyase enzyme by 50%.	None	18.0 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	47.15 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.05 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	5.014 %
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	2.93 %		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	0.02 %		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	2.93 %		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	0.02 %

Cross References

Resources	Reference
ChEBI	68639
ChEMBL	CHEMBL271227
DrugCentral	4176
FDA SRS	EM5OCB9YJ6
Guide to Pharmacology	9288
KEGG	D09701
PubChem	9821849
SureChEMBL	SCHEMBL93715
ZINC	ZINC000003809191

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).