PROGESTERONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1976)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G03DA04
UNII: 4G7DS2Q64Y

Structure
InChI Key RJKFOVLPORLFTN-LEKSSAKUSA-N
Smile CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H30O2
Molecular Weight 314.47
AlogP 4.72
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 34.14
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 23.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.87 - EXP
Henry's Law Constant 6.49E-08 atm-m3/mole EST
Atmospheric OH Rate Constant 1.04E-10 cm3/molecule-sec EST
Melting Point 121 deg C EXP
Water Solubility 8.81 mg/L EXP
Vapor Pressure 1.30E-06 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
AGONIST Progesterone receptor agonist PubMed
Primary Target
Progesterone receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - 20000 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 5500 -
Enzyme Isomerase
- - - 4430 -
Enzyme Oxidoreductase
- 1600-2600 - - 7-19
Enzyme Transferase
- 17000 - - -
Ion channel Ligand-gated ion channel P2X receptor
- 1600 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Steroid-like ligand receptor
2770 - - - -
Membrane receptor
2770 - 239 260 -
Other membrane protein
- - - 660-661 -
Secreted protein
- - 115 42 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 1
- - 4 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 2
- - 4 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 1
- - - 31-31 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 2
- 14-30 0 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 3
0-50 0-17 - 3-5 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 14-37 - 9-35 46
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 33-92
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 56
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 47863-48978 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hemorrhage 4 D006470 ClinicalTrials
Epilepsy 3 D004827 ClinicalTrials
Pregnancy 3 D011247 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Infertility 3 D007246 ClinicalTrials
Premature Birth 3 D047928 ClinicalTrials
Menopause 3 D008593 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Leiomyoma 3 D007889 ClinicalTrials
Ovarian Hyperstimulation Syndrome 3 D016471 ClinicalTrials
Infertility, Female 3 D007247 ClinicalTrials
Diabetes Mellitus 3 D003920 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Memory Disorders 3 D008569 ClinicalTrials
Osteoporosis 3 D010024 ClinicalTrials
Angina, Unstable 3 D000789 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Bone Diseases, Metabolic 3 D001851 ClinicalTrials
Hypercholesterolemia 3 D006937 ClinicalTrials
Thrombosis 3 D013927 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Brain Injuries 3 D001930 ClinicalTrials
Tobacco Use Disorder 2 D014029 ClinicalTrials
Bulimia Nervosa 2 D052018 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Polycystic Ovary Syndrome 2 D011085 ClinicalTrials
Cervical Intraepithelial Neoplasia 2 D018290 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Anorexia Nervosa 2 D000856 ClinicalTrials
Vulvar Lichen Sclerosus 2 D007724 ClinicalTrials
Orthostatic Intolerance 2 D054971 ClinicalTrials
Pre-Eclampsia 2 D011225 ClinicalTrials
Marijuana Abuse 2 D002189 ClinicalTrials
Placenta Previa 2 D010923 ClinicalTrials
Depression, Postpartum 2 D019052 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Coronary Disease 2 D003327 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Diabetes Mellitus, Type 1 1 D003922 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Hot flush
Reproductive system and breast disorders Menopausal symptoms
Nervous system disorders Headache 30.0
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
General disorders and administration site conditions Pain 28.5
Nervous system disorders Headache
General disorders and administration site conditions Pain 25.2
Cardiac disorders Dizziness 24.0
Musculoskeletal and connective tissue disorders Arthralgia 22.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 22.0
Gastrointestinal disorders Abdominal pain 20.0
Gastrointestinal disorders Gastrointestinal pain 20.0
Musculoskeletal and connective tissue disorders Muscle spasms 20.0
Psychiatric disorders Depression 18.0
General disorders and administration site conditions Night sweats
Reproductive system and breast disorders Breast pain 16.0
Reproductive system and breast disorders Breast tenderness 16.0
Cardiac disorders Dizziness 16.0
Nervous system disorders Headache 16.0
Reproductive system and breast disorders Breast tenderness 14.0
General disorders and administration site conditions Hot flush 14.0
Reproductive system and breast disorders Menopausal symptoms 14.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 13.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 13.0
Musculoskeletal and connective tissue disorders Muscle spasms
Musculoskeletal and connective tissue disorders Muscle spasms 13.0
Psychiatric disorders Depression
Nervous system disorders Headache 12.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 12.0
Infections and infestations Viral infection 12.0
Reproductive system and breast disorders Breast pain 11.0
Gastrointestinal disorders Abdominal distension 10.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 10.0
Gastrointestinal disorders Flatulence 10.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 10.0
Nervous system disorders Headache 10.0
Reproductive system and breast disorders Vaginal discharge 10.0
Reproductive system and breast disorders Vulvovaginal dryness
General disorders and administration site conditions Asthenia 9.0
Cardiac disorders Dizziness
General disorders and administration site conditions Fatigue 9.0
Local swelling
Local swelling 9.0
Gastrointestinal disorders Abdominal distension
Gastrointestinal disorders Abdominal distension 8.0
General disorders and administration site conditions Asthenia 8.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 8.0
Reproductive system and breast disorders Breast pain
Reproductive system and breast disorders Breast pain 8.0
Respiratory, thoracic and mediastinal disorders Cough 8.0
Gastrointestinal disorders Diarrhoea 8.0
General disorders and administration site conditions Fatigue 8.0
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 8.0
Nervous system disorders Headache
Nervous system disorders Headache 8.0
General disorders and administration site conditions Irritability 8.0
Gastrointestinal disorders Nausea 8.0
Reproductive system and breast disorders Vulvovaginal dryness 8.0
Gastrointestinal disorders Nausea 7.92
Endocrine disorders Ovarian hyperstimulation syndrome 7.43
Gastrointestinal disorders Nausea 7.18
Gastrointestinal disorders Abdominal distension 7.0
Gastrointestinal disorders Diarrhoea 7.0
Gastrointestinal disorders Flatulence 7.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 7.0
General disorders and administration site conditions Pain 7.0
Reproductive system and breast disorders Vaginal discharge 7.0
Infections and infestations Viral infection 7.0
Gastrointestinal disorders Vomiting
Endocrine disorders Ovarian hyperstimulation syndrome 6.68
Gastrointestinal disorders Abdominal distension 6.0
Psychiatric disorders Affect lability 6.0
Reproductive system and breast disorders Breast pain 6.0
Reproductive system and breast disorders Breast tenderness
Psychiatric disorders Mood swings 6.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 6.0
Gastrointestinal disorders Nausea 6.0
Gastrointestinal disorders Vomiting 6.0
Gastrointestinal disorders Abdominal distension
Psychiatric disorders Anxiety 5.0
Cardiac disorders Chest pain
Cardiac disorders Dizziness 5.0
Gastrointestinal disorders Flatulence
General disorders and administration site conditions Irritability 5.0
General disorders and administration site conditions Night sweats 5.0
Infections and infestations Upper respiratory tract infection 5.0
Gastrointestinal disorders Abdominal distension 4.46
Gastrointestinal disorders Abdominal distension 4.21
Psychiatric disorders Anxiety
General disorders and administration site conditions Asthenia
Cardiac disorders Chest pain 4.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 4.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 4.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Irritability
General disorders and administration site conditions Irritability 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain
Musculoskeletal and connective tissue disorders Musculoskeletal pain 4.0
Nervous system disorders Headache 3.71
Reproductive system and breast disorders Uterine spasm 3.71
Gastrointestinal disorders Constipation 3.47
Reproductive system and breast disorders Vaginal haemorrhage 3.47
Nervous system disorders Headache 3.22
Reproductive system and breast disorders Vaginal haemorrhage 3.22
Gastrointestinal disorders Vomiting 3.22
Gastrointestinal disorders Constipation 3.0
Reproductive system and breast disorders Vaginal discharge
General disorders and administration site conditions Asthenia 2.97
General disorders and administration site conditions Fatigue 2.97
Reproductive system and breast disorders Uterine spasm 2.72
Gastrointestinal disorders Constipation 2.23
Infections and infestations Urinary tract infection 2.23
Gastrointestinal disorders Vomiting 2.23
Reproductive system and breast disorders Breast pain
Gastrointestinal disorders Constipation
General disorders and administration site conditions Asthenia 1.73
General disorders and administration site conditions Fatigue 1.73
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Breast cancer
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Breast cancer 1.0
Infections and infestations Urinary tract infection 0.99

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
11.8
Injury, poisoning and procedural complications
11.1
Nervous system disorders
9.17
Pregnancy, puerperium and perinatal conditions
9.04
Reproductive system and breast disorders
8.88
Vascular disorders
6.5
Skin and subcutaneous tissue disorders
6.15
Psychiatric disorders
5.65
Gastrointestinal disorders
5.5
Respiratory, thoracic and mediastinal disorders
3.78
Cardiac disorders
3.16
Immune system disorders
3.02
Product issues
2.83
Musculoskeletal and connective tissue disorders
2.62
Investigations
2.48

Cross References

Resources Reference
CAS NUMBER 57-83-0
ChEBI 17026
ChEMBL CHEMBL103
DrugBank DB00396
DrugCentral 2279
EPA CompTox DTXSID3022370
FDA SRS 4G7DS2Q64Y
Human Metabolome Database HMDB0001830
Guide to Pharmacology 2377
KEGG C00410
PDB STR
PharmGKB PA451123
PubChem 5994
SureChEMBL SCHEMBL7671
ZINC ZINC000004428529
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