NORETHINDRONE ACETATE

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Trade Names	AYGESTIN NORETHINDRONE ACETATE NORLUTATE
Synonyms	Aygestin NSC-22844 Norethidrone Acetate Norethindrone acetate Norethisteron acetate Norethisterone 17-acetate Norethisterone acetate Norethisteroni acetas Norethynyltestosterone Norlutate Norlutin acetate SH-420
Status
Molecule Category	Free-form
UNII	9S44LIC7OJ
EPA CompTox	DTXSID4023381
Parent Compound:	NORETHINDRONE


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

Structure


InChI Key	IMONTRJLAWHYGT-ZCPXKWAGSA-N
Smiles	C#C[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
InChI	InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H28O3
Molecular Weight	340.46
AlogP	4.06
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	1.0
Polar Surface Area	43.37
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	25.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action	Action	Reference
Progesterone receptor agonist	AGONIST	PubMed PubMed PubMed PubMed


Protein: Progesterone receptor Description: Progesterone receptor Organism : Homo sapiens P06401 ENSG00000082175

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	-	-	-	-	105

Assay Description	Organism	Bioactivity	Reference
DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020)	Bos taurus	28.0 nM		DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020)	Bos taurus	3.615 nM
DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone)	Escherichia coli	106.0 nM		DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone)	Escherichia coli	71.0 nM
DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	None	800.0 nM
DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone)	None	646.0 nM		DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone)	None	293.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	106.88 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	104.95 %
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	11.13 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	-1.23 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	-0.71 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	11.72 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	20.02 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	6.32 %
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	-4.57 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	17.53 %
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	0.25 %		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	0.25 %

Cross References

Resources	Reference
ChEBI	7628
ChEMBL	CHEMBL1201146
DrugCentral	1963
FDA SRS	9S44LIC7OJ
KEGG	C08152
PubChem	5832
SureChEMBL	SCHEMBL37530
ZINC	ZINC000001849528

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).