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Compound Detail

CHEMBL717

MEDROXYPROGESTERONE ACETATE
💊 Approved Drug
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💊 Approved Drug
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C

Basic Information

ChEMBL ID CHEMBL717
Name MEDROXYPROGESTERONE ACETATE
Phase Approved
Structure Type MOL
InChI Key PSGAAPLEWMOORI-PEINSRQWSA-N
Therapeutic ✓ Yes

Known Names

Adgyn medro Amen Climanor Curretab Cycrin Depo-progevera Depo-provera Depo-provera oncology Depo-subq provera 104 Depot-medroxyprogesterone acetate Farlutal Farlutal 100 +18 more
20
Targets
82
Activities
4
Assay Types
1
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

386.5
MW (Da)
4.66
ALogP
4
HBA
0
HBD
60.4
PSA (Ų)
0.65
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1959
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

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

Extended Properties

Molecular Formula C24H34O4
MW 386.53
Aromatic Rings 0
Heavy Atoms 28
NP-Likeness 2.07

Mechanism of Action

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

Indications

Carcinoma, Renal Cell Carcinoma, Renal Cell Endometriosis Hyperplasia Neoplasms Uterine Hemorrhage Bone Diseases Cardiovascular Diseases Coronary Disease Diabetes Mellitus Endometrial Neoplasms Endometrial Neoplasms Heart Diseases Hot Flashes Hypercholesterolemia Hypertension Infertility Kidney Neoplasms Lupus Erythematosus, Systemic Menopause

ATC Classification

G03AC06
medroxyprogesterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03DA02
medroxyprogesterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
L02AB02
medroxyprogesterone
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Drug Warnings

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

Activity Summary

IC50 34 meas. best 8.65
Ki 24 meas. best 9.53
EC50 22 meas. best 10.0
Kd 2 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Progesterone receptor
CHEMBL208
EC50 10.0 9.668 0.1 15
Progesterone receptor
CHEMBL1909044
Ki 9.53 9.53 0.3 1
Progesterone receptor
CHEMBL208
Ki 9.47 9.3925 0.3 8
Androgen receptor
CHEMBL1871
Kd 9.0 9.0 1.0 1
Progesterone receptor
CHEMBL1909044
IC50 8.65 8.65 2.2 1
Androgen receptor
CHEMBL1871
Ki 8.54 8.54 2.9 5
Androgen receptor
CHEMBL3072
Ki 8.31 8.31 4.8 1
Androgen receptor
CHEMBL1871
EC50 8.21 8.21 6.1 1
Androgen receptor
CHEMBL1871
IC50 8.21 8.21 6.1 2
Androgen receptor
CHEMBL3056
EC50 8.21 8.21 6.1 2
Androgen receptor
CHEMBL3072
IC50 8.14 7.23 7.3 3
Glucocorticoid receptor
CHEMBL2034
Ki 8.06 7.91 8.6 6
Glucocorticoid receptor
CHEMBL2034
EC50 8.0 8.0 10.0 3
Glucocorticoid receptor
CHEMBL2034
IC50 8.0 7.9067 10.0 3
Progesterone receptor
CHEMBL208
IC50 7.97 7.97 10.8 3
Aldo-keto reductase family 1 member C3
CHEMBL4681
IC50 6.55 6.2233 280.0 3
Sex hormone-binding globulin
CHEMBL3305
Kd 6.2 6.2 631.0 1
Aldo-keto reductase family 1 member C1
CHEMBL5905
IC50 6.16 5.955 700.0 2
Estrogen receptor
CHEMBL2093866
EC50 6.03 6.03 924.0 1
Estrogen receptor
CHEMBL2093866
IC50 6.03 6.03 924.0 2
Mineralocorticoid receptor
CHEMBL1994
IC50 5.92 5.92 1197.0 3
Aldo-keto reductase family 1 member C2
CHEMBL5847
IC50 5.8 5.53 1600.0 3
Unchecked
CHEMBL612545
Ki 5.2 5.035 6305.0 2
Unchecked
CHEMBL612545
IC50 5.11 4.97 7738.0 2
Bile salt export pump
CHEMBL6020
IC50 4.8 4.8 15700.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.65 4.65 22500.0 1
Histamine H2 receptor
CHEMBL1941
Ki 4.56 4.56 27453.0 1
Histamine H2 receptor
CHEMBL1941
IC50 4.55 4.55 27920.0 1
AN3-CA
CHEMBL1075392
IC50 4.43 4.43 37100.0 1
Ishikawa
CHEMBL614649
IC50 4.43 4.43 37000.0 1
HEC-1-A
CHEMBL4296424
IC50 4.29 4.29 51800.0 1
HEC-1B cell line
CHEMBL614817
IC50 4.22 4.22 60400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6.184 ng.hr.mL-1 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 Effective concentration on alkaline phosphatase activity in human T47D breast ca... 12657271
Progesterone receptor EC50 = 0.12 nM 9.92 Effective concentration against PR (progesterone receptor) 12657271
Progesterone receptor EC50 = 0.12 nM 9.92 Agonistic activity against progesterone receptor in alkaline phosphatase assay u... 11859003
Progesterone receptor EC50 = 0.15 nM 9.82 Agonistic activity against human progesterone receptor expressed in CV-1 cells 12954062
Progesterone receptor EC50 = 0.15 nM 9.82 Compound was tested for agonistic activity by cotransfection assay against human... 10212133
Progesterone receptor EC50 = 0.15 nM 9.82 Agonist activity was determined against hPR (human progesterone receptor) compar... 9873735
Progesterone receptor EC50 = 0.15 nM 9.82 Agonistic activity was measured for modulation of hPR-B (human progesterone rece... 9464361
Progesterone receptor EC50 = 0.15 nM 9.82 Effective concentration (EC50) against human progesterone receptor expressed in ... 9784110
Progesterone receptor EC50 = 0.15 nM 9.82 Agonistic activity to the human progesterone receptor (hPR)assayed in CV-1 cells... 9464360
Progesterone receptor Ki = 0.293 nM 9.53 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Progesterone receptor EC50 = 0.33 nM 9.48 Agonistic activity by cotransfection assay against human Progesterone receptor i... 10212133
Progesterone receptor EC50 = 0.33 nM 9.48 Agonistic activity against human progesterone receptor in T47D breast cancer cel... 12954062
Progesterone receptor Ki = 0.34 nM 9.47 Binding affinity was determined against hPR-A (human progesterone receptor) usin... 9873735
Progesterone receptor Ki = 0.34 nM 9.47 Compound was evaluated for its binding affinity against baculovirus expressed Pr... 10212133
Progesterone receptor Ki = 0.34 nM 9.47 Binding affinity towards human progesterone receptor A isoform using progesteron... 12954062
Progesterone receptor Ki = 0.34 nM 9.47 The binding affinity measured using baculovirus-expressed hPR-A in sf21 cells. 9464361
Progesterone receptor Ki = 0.34 nM 9.47 Binding affinity against human progesterone receptor 9784110
Progesterone receptor Ki = 0.34 nM 9.47 The binding affinity on Human progesterone receptor (hPR-A) using progesterone a... 9464360
Progesterone receptor Ki = 0.3388 nM 9.47 Displacement of [3H]progesterone from Progesterone receptor 16821785
Progesterone receptor EC50 = 0.4 nM 9.4 Agonist activity at human progesterone receptor in human T47D cells assessed as ... 18553958

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 36
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
12954062 10.1021/jm020477g Progesterone receptor 5
9464360 10.1021/jm9705768 Progesterone receptor 5
10212133 10.1021/jm980723h Progesterone receptor 5
9873735 10.1016/s0960-894x(98)00608-8 Progesterone receptor 5
18553958 10.1021/jm8004256 Progesterone receptor 5
9784110 10.1021/jm980366a Progesterone receptor 4
12954062 10.1021/jm020477g Unchecked 4
32527541 10.1016/j.bmcl.2020.127239 Ishikawa 4
12657271 10.1016/s0960-894x(03)00128-8 Progesterone receptor 4
926114 10.1021/jm00219a006 Progesterone receptor 4
12657272 10.1016/s0960-894x(03)00129-x Progesterone receptor 4
9464361 10.1021/jm9705770 Progesterone receptor 3
18553958 10.1021/jm8004256 Rattus norvegicus 3
9464360 10.1021/jm9705768 Glucocorticoid receptor 3
9784110 10.1021/jm980366a Androgen receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
9784110 10.1021/jm980366a Glucocorticoid receptor 3
12954062 10.1021/jm020477g Androgen receptor 3

Data from ChEMBL 36 via Core Engine