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Compound Detail

CHEMBL1200848

HYDROXYPROGESTERONE CAPROATE
💊 Approved Drug
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💊 Approved Drug
CCCCCC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C

Basic Information

ChEMBL ID CHEMBL1200848
Name HYDROXYPROGESTERONE CAPROATE
Phase Approved
Structure Type MOL
InChI Key DOMWKUIIPQCAJU-LJHIYBGHSA-N
Therapeutic ✓ Yes

Known Names

17-alpha-hydroxyprogesterone 17-hydroxyprogesterone 17-ohpc 17.alpha.-caproyloxy-p4 17.alpha.-hydroxyprogesterone 17alpha-hydroxyprogesterone Caproate d'hydroxyprogesterone Caproato de hidroxiprogesterona Delalutin Depo-proluton Hidroxiprogesterona Hormofort +17 more
2
Targets
2
Activities
2
Assay Types
2
PK Parameters
20
Publications
29
Known Names
2
Indications
1
Mechanisms

Molecular Properties

428.6
MW (Da)
5.97
ALogP
4
HBA
0
HBD
60.4
PSA (Ų)
0.39
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Withdrawn Natural Product
USAN Stem -gest-; -ster-; -terone

Extended Properties

Molecular Formula C27H40O4
MW 428.61
Aromatic Rings 0
Heavy Atoms 31
NP-Likeness 1.73

Mechanism of Action

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

Indications

Premature Birth Pregnancy

ATC Classification

G03DA03
hydroxyprogesterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Drug Warnings

Withdrawn
carcinogenicity
possible but unconfirmed risk of cancer
Country: European Union   Year: 2024
Withdrawn
carcinogenicity
increased risk of cancer in offspring exposed to 17-OHPC in utero
Country: European Union   Year: 2024

Activity Summary

EC50 1 meas. best 5.31
IC50 1 meas. best 5.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protein RecA
CHEMBL1741171
EC50 5.31 5.31 4880.0 1
SARS-CoV-2
CHEMBL4303835
IC50 5.2 5.2 6300.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 20.0 nM Homo sapiens
Cmax 70.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
23129211 10.1124/dmd.112.044891 Hepatocyte 10
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23129211 10.1124/dmd.112.044891 Bile salt export pump 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 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
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
926114 10.1021/jm00219a006 Progesterone receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
- 10.1101/2020.03.20.999730 ADMET 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.1101/2020.03.20.999730 SARS-CoV-2 1
23129211 10.1124/dmd.112.044891 Plasma 1

Data from ChEMBL 36 via Core Engine