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Compound Detail

CHEMBL1162

NORETHINDRONE
💊 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@@]21C

Basic Information

ChEMBL ID CHEMBL1162
Name NORETHINDRONE
Phase Approved
Structure Type MOL
InChI Key VIKNJXKGJWUCNN-XGXHKTLJSA-N
Therapeutic ✓ Yes

Known Names

Activella Anovule Calluna vulgaris Calluna vulgaris whole Camila Combipatch Errin Femhrt Gestest Heather Heather whole Incassia +18 more
10
Targets
23
Activities
4
Assay Types
2
PK Parameters
20
Publications
30
Known Names
13
Indications
1
Mechanisms

Molecular Properties

298.4
MW (Da)
3.49
ALogP
2
HBA
1
HBD
37.3
PSA (Ų)
0.70
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1962
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C20H26O2
MW 298.43
Aromatic Rings 0
Heavy Atoms 22
NP-Likeness 1.89

Mechanism of Action

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

Indications

Dysmenorrhea Endometriosis Menopause Pain Sexual Dysfunction, Physiological Hyperandrogenism Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Relapsing-Remitting Reperfusion Injury Hepatitis C Neoplasms Neoplasms

ATC Classification

G03AC01
norethisterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03DC02
norethisterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 11 meas. best 8.49
Ki 8 meas. best 8.91
Kd 3 meas. best 9.4
EC50 1 meas. best 8.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Progesterone receptor
CHEMBL208
Kd 9.4 9.4 0.4 1
Estrogen receptor
CHEMBL2094114
Kd 9.2 9.2 0.6 1
Progesterone receptor
CHEMBL1909044
Ki 8.91 8.91 1.2 1
Progesterone receptor
CHEMBL208
Ki 8.73 8.73 1.9 1
Progesterone receptor
CHEMBL208
EC50 8.66 8.66 2.2 1
Progesterone receptor
CHEMBL208
IC50 8.49 8.49 3.2 1
Progesterone receptor
CHEMBL1909044
IC50 8.03 8.03 9.3 1
Sex hormone-binding globulin
CHEMBL3305
Kd 7.97 7.97 10.7 1
Androgen receptor
CHEMBL3072
Ki 7.82 7.82 15.0 1
Androgen receptor
CHEMBL3072
IC50 7.66 7.29 22.0 2
Glucocorticoid receptor
CHEMBL2034
Ki 6.71 6.71 197.0 1
Estrogen receptor
CHEMBL206
Ki 6.64 6.64 231.0 1
Glucocorticoid receptor
CHEMBL2034
IC50 6.36 6.36 433.0 1
Estrogen receptor
CHEMBL206
IC50 6.09 6.09 808.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.62 5.62 2411.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.34 5.34 4537.0 1
Unchecked
CHEMBL612545
Ki 4.96 4.91 10872.0 2
Unchecked
CHEMBL612545
IC50 4.88 4.845 13343.0 2
Bile salt export pump
CHEMBL6020
IC50 4.73 4.54 18460.0 2

Pharmacokinetic Data

Parameter Value Units Species
F 79.0 % Homo sapiens
F 64.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Progesterone receptor Kd = 0.4 nM 9.4 Dissociation constant for progesterone receptor 15189034
Estrogen receptor Kd = 0.63 nM 9.2 Equilibrium dissociation constant for rat uterine estrogen receptor binding [3H]... 6471068
Progesterone receptor Ki = 1.218 nM 8.91 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Progesterone receptor Ki = 1.87 nM 8.73 The binding affinity measured using baculovirus-expressed hPR-A in sf21 cells. 9464361
Progesterone receptor EC50 = 2.2 nM 8.66 Agonistic activity was measured for modulation of hPR-B (human progesterone rece... 9464361
Progesterone receptor IC50 = 3.2 nM 8.49 Binding affinity against Progesterone receptor in human TE85 osteosarcoma cells ... 8523400
Progesterone receptor IC50 = 9.342 nM 8.03 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Sex hormone-binding globulin Kd = 10.72 nM 7.97 Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding gl... 18330978
Androgen receptor Ki = 15.0 nM 7.82 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Androgen receptor IC50 = 22.0 nM 7.66 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Androgen receptor IC50 = 120.23 nM 6.92 Inhibitory concentration against recombinant rat androgen receptor expressed in ... 16134935
Glucocorticoid receptor Ki = 197.0 nM 6.71 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Estrogen receptor Ki = 231.0 nM 6.64 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Glucocorticoid receptor IC50 = 433.0 nM 6.36 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Estrogen receptor IC50 = 808.0 nM 6.09 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Sodium-dependent serotonin transporter Ki = 2411.0 nM 5.62 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 4537.0 nM 5.34 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Unchecked Ki = 10872.0 nM 4.96 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -
Unchecked IC50 = 13343.0 nM 4.88 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -
Unchecked Ki = 13780.0 nM 4.86 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 837
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
2897467 10.1021/jm00401a015 Glucocorticoid receptor 4
926114 10.1021/jm00219a006 Progesterone receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
9464361 10.1021/jm9705770 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
10891117 10.1021/jm0000564 No relevant target 2
10891117 10.1021/jm0000564 ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
2002446 10.1021/jm00107a021 Androgen receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2

Data from ChEMBL 36 via Core Engine