LEVONORGESTREL

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Search structure


Trade Names	ATHENTIA NEXT FALLBACK SOLO HER STYLE JADELLE KYLEENA LEVONORGESTREL LILETTA MIRENA NORPLANT NORPLANT SYSTEM IN PLASTIC CONTAINER OPCICON ONE-STEP PLAN B PLAN B ONE-STEP SKYLA
Synonyms	Athentia next BAY86-5028 Emerres Emerres una Ezinelle Fallback solo Her style Isteranda Jadelle Jaydess Kyleena Levonelle Levonelle one step Levonelle-2 Levonorgestrel Levonorgestrelum Levosert Liletta Microval Mirena NSC-744007 Norgeston Norgestrel (-)-form Norgestrel, (-)- Norplant Norplant Ii Norplant System Opcicon one-step Ovrette Plan B Plan b one-step Postinor-2 Skyla Upostelle WY-5104
Status
Molecule Category	Free-form
ATC	G03AC03 G03AD01
UNII	5W7SIA7YZW
EPA CompTox	DTXSID3036496


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

Structure


InChI Key	WWYNJERNGUHSAO-XUDSTZEESA-N
Smiles	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC
InChI	InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H28O2
Molecular Weight	312.45
AlogP	3.88
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	1.0
Polar Surface Area	37.3
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
Progesterone receptor agonist	AGONIST	PubMed Wikipedia


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

Assay Description	Organism	Bioactivity	Reference
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	8.4 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	3.88 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	13.61 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	11.18 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	31.67 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	3.12 %
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	2.67 %
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	12.92 %		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	8.27 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	24.83 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	10.36 %
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	0.2 %		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	0.07 %		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	0.07 %		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	0.2 %

Related Entries

Cross References

Resources	Reference
ChEBI	6443
ChEMBL	CHEMBL1389
DrugBank	DB00367
DrugCentral	1572
FDA SRS	5W7SIA7YZW
Human Metabolome Database	HMDB0014511
Guide to Pharmacology	2881
KEGG	C08153
PDB	NOG
PharmGKB	PA450656
PubChem	13109
SureChEMBL	SCHEMBL27597
ZINC	ZINC000003814395

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).