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Compound Detail

CHEMBL103

PROGESTERONE
💊 Approved Drug
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💊 Approved Drug
CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Basic Information

ChEMBL ID CHEMBL103
Name PROGESTERONE
Phase Approved
Structure Type MOL
InChI Key RJKFOVLPORLFTN-LEKSSAKUSA-N
Therapeutic ✓ Yes

Known Names

Crinone Cyclogest Endometrin Lutigest Milprosa NSC-64377 NSC-9704 Prochieve Progesta-care Progestasert Progesterona Progesterone +10 more
34
Targets
131
Activities
4
Assay Types
5
PK Parameters
20
Publications
22
Known Names
20
Indications
1
Mechanisms

Molecular Properties

314.5
MW (Da)
4.72
ALogP
2
HBA
0
HBD
34.1
PSA (Ų)
0.70
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1976
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -gest-; -ster-; -terone

Extended Properties

Molecular Formula C21H30O2
MW 314.47
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 2.23

Mechanism of Action

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

Indications

Amenorrhea Endometrial Hyperplasia Uterine Hemorrhage Alzheimer Disease Angina, Unstable Bone Diseases Bone Diseases, Metabolic Brain Injuries Breast Neoplasms Breast Neoplasms Breast Neoplasms Cardiovascular Diseases Coronary Disease Diabetes Mellitus Epilepsy Hypercholesterolemia Hypertension Infertility Infertility, Female Leiomyoma

ATC Classification

G03DA04
progesterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
vascular toxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States

Activity Summary

IC50 54 meas. best 9.7
Ki 42 meas. best 8.47
EC50 30 meas. best 10.0
Kd 5 meas. best 9.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Progesterone receptor
CHEMBL208
EC50 10.0 8.6817 0.1 24
Progesterone receptor
CHEMBL208
IC50 9.7 8.5575 0.2 4
Mineralocorticoid receptor
CHEMBL1994
Kd 9.41 9.41 0.4 1
Unchecked
CHEMBL612545
IC50 8.47 5.9267 3.4 3
Progesterone receptor
CHEMBL208
Ki 8.47 8.4446 3.4 13
Progesterone receptor
CHEMBL1909044
Ki 8.44 8.44 3.6 1
Estrogen receptor
CHEMBL2094114
Kd 8.41 8.41 3.9 1
Progesterone receptor
CHEMBL3456
IC50 8.22 8.22 6.0 2
Androgen receptor
CHEMBL1871
Ki 8.07 7.9829 8.5 7
Progesterone receptor
CHEMBL3456
Ki 7.98 7.98 10.4 1
Androgen receptor
CHEMBL1871
IC50 7.86 7.5017 13.7 6
Mineralocorticoid receptor
CHEMBL1994
IC50 7.85 7.784 14.0 5
Fatty acid-binding protein, liver
CHEMBL5738
Ki 7.57 7.57 27.0 1
Progesterone receptor
CHEMBL1909044
IC50 7.55 7.55 28.0 1
Glucocorticoid receptor
CHEMBL2034
Ki 7.52 7.42 30.5 7
Androgen receptor
CHEMBL3056
IC50 7.43 7.43 37.0 1
Corticosteroid-binding globulin
CHEMBL2421
Ki 7.38 7.38 41.7 1
Sex hormone-binding globulin
CHEMBL3305
Kd 6.94 6.94 114.8 1
Androgen receptor
CHEMBL3072
Ki 6.84 6.84 143.0 1
Androgen receptor
CHEMBL3072
IC50 6.67 6.24 214.0 2
Sigma non-opioid intracellular receptor 1
CHEMBL3602
Kd 6.62 6.62 239.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.58 6.235 260.0 2
Glucocorticoid receptor
CHEMBL2034
IC50 6.48 6.48 330.0 1
Unchecked
CHEMBL612545
Kd 6.36 6.36 441.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
Ki 6.18 6.18 660.0 2
Solute carrier family 22 member 2
CHEMBL1770032
IC50 5.8 5.8 1600.0 1
P2X purinoceptor 3
CHEMBL2998
IC50 5.8 5.8 1600.0 1
Steroid 5-alpha-reductase
CHEMBL2096664
IC50 5.8 5.69 1600.0 2
G-protein coupled bile acid receptor 1
CHEMBL5409
EC50 5.56 5.56 2770.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 5.52 5.52 3050.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 5.51 5.51 3055.0 1
Solute carrier family 22 member 3
CHEMBL2073673
IC50 5.37 5.37 4280.0 1
C-8 sterol isomerase ERG2
CHEMBL3224
Ki 5.35 5.35 4430.0 1
Cytochrome P450 2C9
CHEMBL3397
Ki 5.26 5.26 5500.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.2 4.9457 6309.6 7
Unchecked
CHEMBL612545
Ki 5.17 4.91 6703.0 2
Solute carrier family 22 member 3
CHEMBL1770033
IC50 4.98 4.98 10500.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.97 4.6567 10600.0 3
Sterol O-acyltransferase 1
CHEMBL2782
IC50 4.77 4.77 17000.0 1
Bile salt export pump
CHEMBL6020
IC50 4.76 4.76 17300.0 1
Breast cancer cell line
CHEMBL614788
EC50 4.73 4.69 18700.0 2
Fatty acid-binding protein, intestinal
CHEMBL4879
Ki 4.7 4.7 20000.0 1
Unchecked
CHEMBL612545
EC50 4.68 4.53 21000.0 2
ATP-dependent translocase ABCB1
CHEMBL4302
EC50 4.67 4.67 21200.0 1
Solute carrier family 22 member 2
CHEMBL1743122
IC50 4.57 4.57 26700.0 1
Monoclonal antibody (mAb)
CHEMBL613294
Ki 4.44 4.44 36000.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 4.32 4.204 47863.0 5

Pharmacokinetic Data

Parameter Value Units Species
Cmax 193.0 nM Homo sapiens
F 20.0 % Homo sapiens
Fu 0.67 - Homo sapiens
T1/2 240.0 hr -
T1/2 0.4167 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Progesterone receptor EC50 = 0.1 nM 10.0 Activation of progesterone receptor in human T47D cells after 20 hrs by PRE-tagg... 19863083
Progesterone receptor EC50 = 0.18 nM 9.74 Agonist activity at PR in human T47D cells using p-nitrophenyl phosphate as subs... 34607200
Progesterone receptor IC50 = 0.2 nM 9.7 Binding affinity to progesterone receptor 24900290
Mineralocorticoid receptor Kd = 0.39 nM 9.41 Affinity for recombinant Mineralocorticoid receptor 8709117
Progesterone receptor EC50 = 0.5 nM 9.3 Agonist activity at human progesterone receptor 18553958
Progesterone receptor EC50 = 0.9 nM 9.05 Effective concentration on alkaline phosphatase activity in human T47D breast ca... 12657271
Progesterone receptor EC50 = 0.9 nM 9.05 Activity at progesterone receptor assessed as alkaline phosphatase activity in h... 18722119
Progesterone receptor EC50 = 0.92 nM 9.04 Effective concentration against PR (progesterone receptor) 12657271
Progesterone receptor EC50 = 0.92 nM 9.04 Agonistic activity against progesterone receptor in alkaline phosphatase assay u... 11859003
Progesterone receptor EC50 = 1.5 nM 8.82 Effective concentration for half-maximal activation of human progesterone recept... 9667968
Progesterone receptor EC50 = 1.8 nM 8.74 Agonistic activity against human progesterone receptor in T47D breast cancer cel... 12954062
Progesterone receptor EC50 = 1.8 nM 8.74 Agonistic activity by cotransfection assay against human Progesterone receptor i... 10212133
Progesterone receptor EC50 = 1.8 nM 8.74 Human progesterone receptor (hPR) agonist activity in T47D human breast cancer c... 10743938
Progesterone receptor EC50 = 2.0 nM 8.7 Agonist activity at human PRGR expressed in HEK293 cells by luciferase reporter ... 25305688
Progesterone receptor EC50 = 2.2 nM 8.66 Agonist activity at human progesterone receptor in human T47D cells assessed as ... 18553958
Progesterone receptor EC50 = 2.9 nM 8.54 Agonistic activity to the human progesterone receptor (hPR)assayed in CV-1 cells... 9464360
Progesterone receptor EC50 = 2.9 nM 8.54 Effective concentration (EC50) against human progesterone receptor expressed in ... 9784110
Progesterone receptor EC50 = 2.89 nM 8.54 Agonistic activity was measured for modulation of hPR-B (human progesterone rece... 9464361
Progesterone receptor EC50 = 2.9 nM 8.54 Effective concentration for agonist activity towards human progesterone receptor... 12781197
Progesterone receptor EC50 = 2.9 nM 8.54 Agonistic activity against human progesterone receptor in CV-1 cells 12954062

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 430
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
16789751 10.1021/jm060230+ ADMET 9
10743938 10.1016/s0960-894x(00)00011-1 Progesterone receptor 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
11784143 10.1021/jm010126m Breast cancer cell line 7
2897467 10.1021/jm00401a015 Glucocorticoid receptor 7
12109909 10.1021/jm0102811 Monoclonal antibody (mAb) 6
423192 10.1021/jm00188a004 Oryctolagus cuniculus 6
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
20014752 10.1021/tx900326k Hepatotoxicity 6
9464360 10.1021/jm9705768 Progesterone receptor 5
12954062 10.1021/jm020477g Progesterone receptor 5
12781197 10.1016/s0960-894x(03)00255-5 Progesterone receptor 5
9873735 10.1016/s0960-894x(98)00608-8 Progesterone receptor 5
34935393 10.1021/acs.jnatprod.1c01008 ADMET 5
10212133 10.1021/jm980723h Progesterone receptor 5
9784110 10.1021/jm980366a Progesterone receptor 4
11784143 10.1021/jm010126m Unchecked 4

Data from ChEMBL 36 via Core Engine