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Compound Detail

CHEMBL1389

LEVONORGESTREL
💊 Approved Drug
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💊 Approved Drug
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC

Basic Information

ChEMBL ID CHEMBL1389
Name LEVONORGESTREL
Phase Approved
Structure Type MOL
InChI Key WWYNJERNGUHSAO-XUDSTZEESA-N
Therapeutic ✓ Yes

Known Names

Athentia next BAY86-5028 Emerres Emerres una Ezinelle Fallback solo Her style Isteranda Jadelle Jaydess Kyleena Levonelle +18 more
1
Targets
2
Activities
1
Assay Types
5
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

312.4
MW (Da)
3.88
ALogP
2
HBA
1
HBD
37.3
PSA (Ų)
0.75
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability OTC
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Stem -estr-; -gest-
USAN Year 1980

Extended Properties

Molecular Formula C21H28O2
MW 312.45
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 1.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Progesterone receptor agonist AGONIST Progesterone receptor

Indications

Menorrhagia Anorexia Nervosa Bone Diseases, Metabolic Dysmenorrhea Endometriosis Hemorrhage Migraine Disorders Adenomyosis Endometrial Neoplasms HIV Infections HIV Infections Ovarian Neoplasms Pain Pregnancy Diabetes Mellitus Diabetes Mellitus, Type 2 Hepatitis B, Chronic Hepatitis C, Chronic Leukemia, Lymphocytic, Chronic, B-Cell Neoplasms

ATC Classification

G03AC03
levonorgestrel
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03AD01
levonorgestrel
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Activity Summary

EC50 2 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Progesterone receptor
CHEMBL208
EC50 9.0 9.0 1.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 1.8 mL.min-1.kg-1 Homo sapiens
F 87.0 % Homo sapiens
Fu 0.025 - Homo sapiens
MRT 14.0 hr Homo sapiens
T1/2 9.4 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 73
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
926114 10.1021/jm00219a006 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
35797110 10.1021/acs.jmedchem.2c00641 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 3 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1

Data from ChEMBL 36 via Core Engine