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Compound Detail

CHEMBL2107797

NORGESTREL
💊 Approved Drug
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💊 Approved Drug
C#CC1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC

Basic Information

ChEMBL ID CHEMBL2107797
Name NORGESTREL
Phase Approved
Structure Type MOL
InChI Key WWYNJERNGUHSAO-CULCCENASA-N
Therapeutic ✓ Yes

Known Names

Dl-norgestrel FH-122A Norgestrel Norgestrel component of cryselle Norgestrel component of ovral NSC-757251 Opill Ovrette Prefest Previfem SH-70850 SH-850 +4 more
6
Targets
12
Activities
3
Assay Types
0
PK Parameters
12
Publications
16
Known Names
2
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 1968
Availability OTC
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -estr-; -gest-
USAN Year 1966

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

Hemorrhage Endometrial Neoplasms

Activity Summary

IC50 6 meas. best 8.46
Ki 5 meas. best 9.34
Kd 1 meas. best 8.91

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Progesterone receptor
CHEMBL1909044
Ki 9.34 9.34 0.5 1
Sex hormone-binding globulin
CHEMBL3305
Kd 8.91 8.91 1.2 1
Progesterone receptor
CHEMBL1909044
IC50 8.46 8.46 3.5 1
Androgen receptor
CHEMBL3072
Ki 8.37 8.37 4.3 1
Androgen receptor
CHEMBL3072
IC50 8.19 7.96 6.4 2
Glucocorticoid receptor
CHEMBL2034
Ki 7.17 7.17 68.0 1
Glucocorticoid receptor
CHEMBL2034
IC50 6.83 6.83 149.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.22 6.22 595.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.95 5.95 1119.0 1
Unchecked
CHEMBL612545
Ki 5.72 5.72 1922.0 1
Unchecked
CHEMBL612545
IC50 5.63 5.63 2359.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Progesterone receptor Ki = 0.458 nM 9.34 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Sex hormone-binding globulin Kd = 1.23 nM 8.91 Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding gl... 18330978
Progesterone receptor IC50 = 3.509 nM 8.46 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Androgen receptor Ki = 4.266 nM 8.37 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Androgen receptor IC50 = 6.399 nM 8.19 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Androgen receptor IC50 = 18.62 nM 7.73 Inhibitory concentration against recombinant rat androgen receptor expressed in ... 16134935
Glucocorticoid receptor Ki = 68.0 nM 7.17 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Glucocorticoid receptor IC50 = 149.0 nM 6.83 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Sodium-dependent serotonin transporter Ki = 595.0 nM 6.22 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 1119.0 nM 5.95 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Unchecked Ki = 1922.0 nM 5.72 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -
Unchecked IC50 = 2359.0 nM 5.63 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -

Literature References

PubMed DOI Target Context # Activities
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
16134935 10.1021/jm050403f Androgen receptor 1
18330978 10.1021/jm7011485 Sex hormone-binding globulin 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
226703 10.1021/jm00194a016 Progesterone receptor 1
20876785 10.1124/dmd.110.032276 Liver microsome 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine