MIFEPRISTONE

Search structure
Trade Names:
Synonyms:
Status: Approved (2000)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G03XB01
UNII: 320T6RNW1F

Structure
InChI Key VKHAHZOOUSRJNA-GCNJZUOMSA-N
Smile CC#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(N(C)C)cc3)C[C@@]21C
InChI
InChI=1S/C29H35NO2/c1-5-15-29(32)16-14-26-24-12-8-20-17-22(31)11-13-23(20)27(24)25(18-28(26,29)2)19-6-9-21(10-7-19)30(3)4/h6-7,9-10,17,24-26,32H,8,11-14,16,18H2,1-4H3/t24-,25+,26-,28-,29-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H35NO2
Molecular Weight 429.6
AlogP 5.41
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 40.54
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 32.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Glucocorticoid receptor antagonist PubMed DailyMed
Primary Target
Glucocorticoid receptor
Progesterone receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 1500-1500 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 4900 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 9500-9500 - 4700-4700 -
Enzyme Transferase
- - - - 101
Other nuclear protein
1 - - - -
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
- 5000-5000 - - 44-50
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
- 2244 - 2876 92
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
1-872 0-18 15 0-169 97-100
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
- 590-6000 - 640-851 70-96
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 0-10 - 0-15 98-100
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
10-12 1-89 - 1-22 95
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 71
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 2020 20000 - -
Unclassified protein
- 20-33 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Depressive Disorder, Major 3 D003865 ClinicalTrials
Leiomyoma 3 D007889 ClinicalTrials
Leiomyoma 3 D007889 ClinicalTrials
Abortion, Spontaneous 3 D000022 ClinicalTrials
Pituitary ACTH Hypersecretion 3 D047748 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Meningioma 3 D008579 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Borderline Personality Disorder 2 D001883 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Hepatitis C 2 D006526 ClinicalTrials
Bipolar Disorder 2 D001714 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Endometriosis 2 D004715 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Adenomyosis 2 D062788 ClinicalTrials
Central Serous Chorioretinopathy 2 D056833 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Pregnancy 1 D011247 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Diabetes Mellitus 1 D003920 ClinicalTrials
Persian Gulf Syndrome 1 D018923 ClinicalTrials
Anxiety 1 D001007 ClinicalTrials
Breast Neoplasms, Male 1 D018567 ClinicalTrials
Tobacco Use Disorder 0 D014029 ClinicalTrials
Carcinoma, Intraductal, Noninfiltrating 0 D002285 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Asthenia 48.0
General disorders and administration site conditions Fatigue 48.0
Nervous system disorders Headache 44.0
Reproductive system and breast disorders Endometrial hypertrophy 38.0
Investigations Blood potassium decreased 34.0
Musculoskeletal and connective tissue disorders Arthralgia 30.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 30.0
Cardiac disorders Oedema peripheral 26.0
Gastrointestinal disorders Vomiting 26.0
Vascular disorders Hypertension 24.0
Cardiac disorders Dizziness 22.0
General disorders and administration site conditions Decreased appetite 20.0
Gastrointestinal disorders Dry mouth 18.0
Investigations Thyroid function test abnormal 18.0
Musculoskeletal and connective tissue disorders Back pain 16.0
Cardiac disorders Dyspnoea 16.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 14.0
Musculoskeletal and connective tissue disorders Myalgia 14.0
General disorders and administration site conditions Pain 14.0
Infections and infestations Sinusitis 14.0
Gastrointestinal disorders Diarrhoea 12.0
Infections and infestations Nasopharyngitis 12.0
Musculoskeletal and connective tissue disorders Pain in extremity 12.0
Psychiatric disorders Anxiety 10.0
Gastrointestinal disorders Constipation 10.0
General disorders and administration site conditions Decreased appetite 10.0
Nervous system disorders Somnolence 10.0
Skin and subcutaneous tissue disorders Pruritus 4.0
Vascular disorders Hypotension 0.25

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
13.74
Investigations
9.65
Vascular disorders
8.18
Gastrointestinal disorders
8.11
Nervous system disorders
7.66
Cardiac disorders
6.17
Reproductive system and breast disorders
5.75
Musculoskeletal and connective tissue disorders
5.43
Respiratory, thoracic and mediastinal disorders
4.43
Metabolism and nutrition disorders
4.42
Infections and infestations
3.63
Psychiatric disorders
3.58
Pregnancy, puerperium and perinatal conditions
3.2
Skin and subcutaneous tissue disorders
3.16
Injury, poisoning and procedural complications
3.12
Renal and urinary disorders
2.27

Cross References

Resources Reference
CAS NUMBER 84371-65-3
ChEBI 50692
ChEMBL CHEMBL1276308
DrugBank DB00834
DrugCentral 1805
EPA CompTox DTXSID5023322
FDA SRS 320T6RNW1F
Human Metabolome Database HMDB0014972
Guide to Pharmacology 2805
KEGG C07652
PDB 486
PharmGKB PA450500
PubChem 55245
SureChEMBL SCHEMBL16087
ZINC ZINC000003831128
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