ESTRADIOL

Search structure
Trade Names:
Synonyms:
Status: Approved (1975)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G03CA03
UNII: 4TI98Z838E

Structure
InChI Key VOXZDWNPVJITMN-ZBRFXRBCSA-N
Smile C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
InChI
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H24O2
Molecular Weight 272.39
AlogP 3.61
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 0.0
Polar Surface Area 40.46
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 20.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Estrogen receptor alpha agonist DailyMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1B Cytochrome P450 1B1
- - - 1900 12
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
4100 - - - -
Enzyme Hydrolase
- 84000-84000 - - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC alpha subfamily
- - - - 77-89
Enzyme Oxidoreductase
- 12000 - 870-4400 0-1
Enzyme Transferase
- - 1200-2300 - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 50000 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 18-53
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
0-0 - - 3-6 -
Secreted protein
- 50 2 10000 -
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
0-130 0-46 0-1 0-100 78-100
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
0-280 0-24 0-1 0-0 100
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group B Nuclear hormone receptor subfamily 3 group B member 1
6 4-6 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group B Nuclear hormone receptor subfamily 3 group B member 2
5 3-9 - - -
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
- 19-26 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 103-126
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 84
Unclassified protein
- 60000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Dyspareunia 4 D004414 ClinicalTrials
Anorexia Nervosa 3 D000856 ClinicalTrials
Turner Syndrome 3 D014424 ClinicalTrials
Infertility 3 D007246 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Menopause 3 D008593 ClinicalTrials
Sexual Dysfunction, Physiological 3 D012735 ClinicalTrials
Endometriosis 3 D004715 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Obesity 3 D009765 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Atrophy 3 D001284 ClinicalTrials
Atrophic Vaginitis 3 D059268 ClinicalTrials
Bone Diseases, Metabolic 3 D001851 ClinicalTrials
Leiomyoma 3 D007889 ClinicalTrials
Dysmenorrhea 3 D004412 ClinicalTrials
Stress Disorders, Post-Traumatic 3 D013313 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Amenorrhea 3 D000568 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Hot Flashes 3 D019584 ClinicalTrials
Atrophic Vaginitis 3 D059268 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Non-alcoholic Fatty Liver Disease 3 D065626 ClinicalTrials
Hereditary Breast and Ovarian Cancer Syndrome 2 D061325 ClinicalTrials
Migraine Disorders 2 D008881 ClinicalTrials
Depressive Disorder 2 D003866 ClinicalTrials
Carcinoid Tumor 2 D002276 ClinicalTrials
Psychotic Disorders 2 D011618 ClinicalTrials
Bulimia Nervosa 2 D052018 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Aging 2 D000375 ClinicalTrials
Atherosclerosis 2 D050197 ClinicalTrials
Dry Eye Syndromes 2 D015352 ClinicalTrials
Depression, Postpartum 2 D019052 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Schizophrenia 2 D012559 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Polycystic Ovary Syndrome 1 D011085 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Diabetes Mellitus, Type 1 1 D003922 ClinicalTrials
Osteoporosis 1 D010024 ClinicalTrials
Cerebral Arterial Diseases 0 D002539 ClinicalTrials

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Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Application site reaction
General disorders and administration site conditions Application site reaction 56.7
General disorders and administration site conditions Application site reaction 55.1
General disorders and administration site conditions Application site reaction 52.8
Nervous system disorders Headache 50.0
Reproductive system and breast disorders Breast pain 34.8
Nervous system disorders Headache 31.1
Reproductive system and breast disorders Breast pain 29.0
Nervous system disorders Headache 26.9
Infections and infestations Respiratory tract infection
Nervous system disorders Headache 25.8
Infections and infestations Respiratory tract infection 24.7
Infections and infestations Respiratory tract infection 24.4
Nervous system disorders Headache
Nervous system disorders Headache 21.3
Infections and infestations Respiratory tract infection 21.3
Nervous system disorders Headache 20.2
Infections and infestations Nasopharyngitis 19.6
Infections and infestations Sinusitis
Nervous system disorders Headache 18.0
Reproductive system and breast disorders Breast pain 17.8
Nervous system disorders Headache
Infections and infestations Infection 17.3
Reproductive system and breast disorders Breast tenderness 17.0
Infections and infestations Upper respiratory tract infection 17.0
Infections and infestations Upper respiratory tract infection
Reproductive system and breast disorders Vaginal haemorrhage 16.7
Infections and infestations Respiratory tract infection 16.1
Gastrointestinal disorders Abdominal pain 16.0
Gastrointestinal disorders Gastrointestinal pain 16.0
Nervous system disorders Headache 16.0
Infections and infestations Upper respiratory tract infection 15.9
Infections and infestations Nasopharyngitis
Reproductive system and breast disorders Endometrial disorder 15.1
Nervous system disorders Headache 14.9
Surgical and medical procedures Vasodilation procedure
Reproductive system and breast disorders Breast pain 14.6
Injury, poisoning and procedural complications Injury 13.9
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Infections and infestations Influenza 13.3
Infections and infestations Sinusitis 13.1
Nervous system disorders Headache 13.0
General disorders and administration site conditions Oedema 13.0
Reproductive system and breast disorders Breast tenderness 12.9
Nervous system disorders Headache
Nervous system disorders Headache
General disorders and administration site conditions Pain
Infections and infestations Sinusitis 12.6
Reproductive system and breast disorders Breast pain 12.5
General disorders and administration site conditions Pain 12.5
Musculoskeletal and connective tissue disorders Arthralgia 12.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 12.4
General disorders and administration site conditions Pain
Infections and infestations Nasopharyngitis 12.3
Nervous system disorders Headache 12.2
Infections and infestations Sinusitis 12.2
Metabolism and nutrition disorders Malnutrition 12.0
Musculoskeletal and connective tissue disorders Arthralgia 11.5
Infections and infestations Infection 11.5
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 11.5
Nervous system disorders Headache 11.2
Musculoskeletal and connective tissue disorders Arthralgia 11.1
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 11.1
Gastrointestinal disorders Abdominal pain 11.0
Gastrointestinal disorders Gastrointestinal pain 11.0
Injury, poisoning and procedural complications Injury
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 11.0
Nervous system disorders Sinus headache 10.9
Reproductive system and breast disorders Breast pain 10.7
Reproductive system and breast disorders Breast tenderness 10.7
Infections and infestations Upper respiratory tract infection 10.7
Infections and infestations Vulvovaginal candidiasis 10.7
Infections and infestations Vulvovaginal mycotic infection 10.7
Musculoskeletal and connective tissue disorders Back pain 10.6
Psychiatric disorders Depression 10.6
Reproductive system and breast disorders Metrorrhagia 10.6
Reproductive system and breast disorders Vaginal discharge 10.6
Nervous system disorders Headache 10.5
Metabolism and nutrition disorders Malnutrition
Infections and infestations Influenza
Infections and infestations Nasopharyngitis 10.3
Infections and infestations Sinusitis
Reproductive system and breast disorders Breast pain 10.1
Infections and infestations Influenza 10.1
General disorders and administration site conditions Pain 10.1
Infections and infestations Sinusitis 10.1
Psychiatric disorders Anxiety 10.0
Infections and infestations Fungal infection 10.0
Nervous system disorders Headache
General disorders and administration site conditions Oedema 10.0
Nervous system disorders Headache 9.82
Reproductive system and breast disorders Metrorrhagia 9.82
Infections and infestations Nasopharyngitis 9.71
Reproductive system and breast disorders Breast pain
Reproductive system and breast disorders Metrorrhagia 9.6
Nervous system disorders Headache 9.5
Nervous system disorders Headache
Nervous system disorders Headache
Gastrointestinal disorders Dyspepsia 9.23
Nervous system disorders Sinus headache 9.23
Nervous system disorders Headache 9.21
Psychiatric disorders Depression
General disorders and administration site conditions Pain 9.2
Reproductive system and breast disorders Metrorrhagia 9.15
Musculoskeletal and connective tissue disorders Back pain 9.0
Reproductive system and breast disorders Breast pain 9.0
Nervous system disorders Headache 9.0
Gastrointestinal disorders Dyspepsia 8.99
Infections and infestations Influenza 8.99
Infections and infestations Influenza
Infections and infestations Vaginal infection 8.9
Vaginal inflammation 8.9
Skin and subcutaneous tissue disorders Dermatitis 8.89
Nervous system disorders Headache 8.89
Injury, poisoning and procedural complications Injury 8.89
Skin and subcutaneous tissue disorders Rash 8.89
Reproductive system and breast disorders Breast tenderness 8.8
Nervous system disorders Headache 8.79
Musculoskeletal and connective tissue disorders Back pain 8.74
Musculoskeletal and connective tissue disorders Back pain 8.7
Infections and infestations Upper respiratory tract infection 8.7
General disorders and administration site conditions Application site reaction 8.65
Nervous system disorders Headache 8.63
General disorders and administration site conditions Application site reaction
Musculoskeletal and connective tissue disorders Back pain 8.51
Gastrointestinal disorders Dyspepsia 8.51
Infections and infestations Influenza 8.51
Infections and infestations Sinusitis 8.51
Investigations Weight increased 8.51
Musculoskeletal and connective tissue disorders Arthralgia 8.46
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 8.46
Infections and infestations Nasopharyngitis 8.45
Infections and infestations Nasopharyngitis 8.33
Reproductive system and breast disorders Reproductive tract disorder
Reproductive system and breast disorders Vaginal discharge
Infections and infestations Vulvovaginal mycotic infection 8.29
Reproductive system and breast disorders Endometrial disorder
Reproductive system and breast disorders Breast pain
Gastrointestinal disorders Abdominal pain 8.17
Gastrointestinal disorders Gastrointestinal pain 8.17
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Reproductive system and breast disorders Breast pain
Nervous system disorders Insomnia
Infections and infestations Vaginal infection 8.05
Vaginal inflammation 8.05
Gastrointestinal disorders Abdominal pain
Musculoskeletal and connective tissue disorders Back pain 8.0
Reproductive system and breast disorders Breast pain 8.0
Psychiatric disorders Depression 8.0
Gastrointestinal disorders Gastrointestinal pain
General disorders and administration site conditions Pain 8.0
Reproductive system and breast disorders Perineal pain 8.0
Infections and infestations Upper respiratory tract infection
Reproductive system and breast disorders Metrorrhagia 7.96
Gastrointestinal disorders Abdominal pain 7.87
General disorders and administration site conditions Asthenia 7.87
Musculoskeletal and connective tissue disorders Back pain 7.87
Infections and infestations Bronchitis 7.87
Gastrointestinal disorders Gastrointestinal pain 7.87
Skin and subcutaneous tissue disorders Pruritus 7.8
Reproductive system and breast disorders Vulvovaginal pruritus 7.8
Cardiac disorders Dizziness 7.78
Reproductive system and breast disorders Breast tenderness 7.77
General disorders and administration site conditions Influenza like illness 7.77
Reproductive system and breast disorders Breast tenderness 7.75
Gastrointestinal disorders Abdominal pain 7.7
Gastrointestinal disorders Gastrointestinal pain 7.7
Musculoskeletal and connective tissue disorders Back pain 7.69
Reproductive system and breast disorders Breast tenderness 7.69
Musculoskeletal and connective tissue disorders Pain in extremity 7.69
Infections and infestations Influenza 7.58
Infections and infestations Sinusitis 7.47
Infections and infestations Infection
Infections and infestations Nasopharyngitis
Musculoskeletal and connective tissue disorders Arthritis
Skin and subcutaneous tissue disorders Dermatitis 7.1
General disorders and administration site conditions Pain 7.1
Skin and subcutaneous tissue disorders Rash 7.1
Gastrointestinal disorders Abdominal distension 7.08
Nervous system disorders Headache 7.08
Reproductive system and breast disorders Breast pain 7.0
Gastrointestinal disorders Flatulence 7.0
Infections and infestations Genital candidiasis 7.0
General disorders and administration site conditions Pain
Gastrointestinal disorders Pharyngitis 7.0
Infections and infestations Urinary tract infection 7.0
Reproductive system and breast disorders Vaginal discharge 7.0
Reproductive system and breast disorders Metrorrhagia 6.92
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Breast neoplasm
Reproductive system and breast disorders Breast pain 6.9
Infections and infestations Bronchitis
Infections and infestations Vaginal infection
Vaginal inflammation
Musculoskeletal and connective tissue disorders Back pain 6.83
Psychiatric disorders Depression 6.8
Infections and infestations Infection
Musculoskeletal and connective tissue disorders Pain in extremity 6.8
Infections and infestations Rhinitis
Reproductive system and breast disorders Breast tenderness 6.76
Skin and subcutaneous tissue disorders Hyperaesthesia 6.76
Reproductive system and breast disorders Nipple pain 6.76
Reproductive system and breast disorders Breast enlargement 6.74
Skin and subcutaneous tissue disorders Dermatitis 6.74
Vascular disorders Hypertension 6.74
Injury, poisoning and procedural complications Injury 6.74
Nervous system disorders Migraine 6.74
Gastrointestinal disorders Nausea 6.74
General disorders and administration site conditions Pain 6.74
Skin and subcutaneous tissue disorders Pruritus 6.74
Skin and subcutaneous tissue disorders Rash 6.74
Infections and infestations Sinusitis 6.74
Surgical and medical procedures Vasodilation procedure 6.74
Gastrointestinal disorders Constipation 6.67
General disorders and administration site conditions Cyst 6.67
Reproductive system and breast disorders Vaginal haemorrhage 6.67
Reproductive system and breast disorders Breast tenderness 6.62
Gastrointestinal disorders Abdominal pain 6.59
Musculoskeletal and connective tissue disorders Back pain 6.59
Gastrointestinal disorders Gastrointestinal pain 6.59
Nervous system disorders Headache
Reproductive system and breast disorders Breast tenderness 6.52
Gastrointestinal disorders Constipation 6.52
Reproductive system and breast disorders Dysmenorrhoea 6.52
Respiratory, thoracic and mediastinal disorders Sinus congestion 6.52
Infections and infestations Sinusitis 6.52
Gastrointestinal disorders Flatulence 6.5
Gastrointestinal disorders Nausea
Infections and infestations Vulvovaginitis
Infections and infestations Sinusitis 6.47
Infections and infestations Vulvovaginal mycotic infection 6.4
Psychiatric disorders Anxiety 6.38
Musculoskeletal and connective tissue disorders Back pain
Nervous system disorders Headache
General disorders and administration site conditions Hot flush 6.38
General disorders and administration site conditions Influenza like illness 6.38
Nervous system disorders Insomnia 6.38
Reproductive system and breast disorders Menopausal symptoms 6.38
Reproductive system and breast disorders Metrorrhagia 6.38
Infections and infestations Nasopharyngitis 6.38
Musculoskeletal and connective tissue disorders Neck pain 6.38
Infections and infestations Upper respiratory tract infection 6.38
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Influenza like illness
Musculoskeletal and connective tissue disorders Back pain 6.32
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Cervical polyp 6.25
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Back pain 6.19
Reproductive system and breast disorders Breast tenderness 6.19
Infections and infestations Vulvovaginal candidiasis 6.19
Infections and infestations Vulvovaginal mycotic infection 6.19
Gastrointestinal disorders Nausea 6.15
General disorders and administration site conditions Pain 6.15
Infections and infestations Upper respiratory tract infection 6.15
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 6.0
Infections and infestations Genital candidiasis 6.0
Nervous system disorders Headache
Gastrointestinal disorders Nausea 6.0
General disorders and administration site conditions Oedema
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Pruritus 6.0
Reproductive system and breast disorders Pruritus genital 6.0
Infections and infestations Rhinitis 6.0
Infections and infestations Upper respiratory tract infection 6.0
Reproductive system and breast disorders Vaginal discharge 6.0
Infections and infestations Vaginal infection
Vaginal inflammation
Infections and infestations Upper respiratory tract infection 5.88
Infections and infestations Influenza 5.83
Reproductive system and breast disorders Metrorrhagia 5.83
Infections and infestations Bronchitis 5.77
General disorders and administration site conditions Application site reaction 5.75
Musculoskeletal and connective tissue disorders Back pain
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Flatulence
Skin and subcutaneous tissue disorders Rash
Infections and infestations Nasopharyngitis 5.74
Infections and infestations Upper respiratory tract infection 5.74
Musculoskeletal and connective tissue disorders Arthralgia
Nervous system disorders Insomnia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Pain in extremity
Infections and infestations Upper respiratory tract infection
Reproductive system and breast disorders Breast tenderness 5.69
Reproductive system and breast disorders Metrorrhagia 5.69
Musculoskeletal and connective tissue disorders Arthralgia 5.62
Musculoskeletal and connective tissue disorders Back pain 5.62
Nervous system disorders Headache 5.62
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.62
Musculoskeletal and connective tissue disorders Myalgia 5.62
Infections and infestations Urinary tract infection 5.62
Gastrointestinal disorders Abdominal pain 5.56
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Breast neoplasm 5.56
Gastrointestinal disorders Gastrointestinal pain 5.56
Gastrointestinal disorders Nausea 5.56
General disorders and administration site conditions Pain 5.56
Infections and infestations Upper respiratory tract infection
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Flatulence
Skin and subcutaneous tissue disorders Rash
Infections and infestations Genital candidiasis 5.49
Infections and infestations Upper respiratory tract infection 5.49
Musculoskeletal and connective tissue disorders Back pain 5.41
Gastrointestinal disorders Flatulence 5.4
Infections and infestations Influenza 5.4
Gastrointestinal disorders Diarrhoea 5.37
Gastrointestinal disorders Nausea
Infections and infestations Vulvovaginitis 5.31
Gastrointestinal disorders Nausea 5.3
General disorders and administration site conditions Pain 5.3
Infections and infestations Sinusitis 5.3
Musculoskeletal and connective tissue disorders Arthritis 5.29
Gastrointestinal disorders Constipation 5.29
Cardiac disorders Dizziness 5.29
Gastrointestinal disorders Dyspepsia 5.29
Infections and infestations Infection 5.29
Musculoskeletal and connective tissue disorders Arthralgia
Reproductive system and breast disorders Breast tenderness
Reproductive system and breast disorders Breast tenderness 5.26
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Infections and infestations Nasopharyngitis 5.26
Nervous system disorders Headache
Injury, poisoning and procedural complications Injury 5.17
Skin and subcutaneous tissue disorders Pruritus 5.17
Nervous system disorders Sinus headache
Gastrointestinal disorders Abdominal pain 5.0
Musculoskeletal and connective tissue disorders Arthralgia 5.0
Reproductive system and breast disorders Breast pain 5.0
Infections and infestations Candida infection 5.0
Psychiatric disorders Depression 5.0
Gastrointestinal disorders Flatulence 5.0
Gastrointestinal disorders Gastrointestinal pain 5.0
Nervous system disorders Headache 5.0
Infections and infestations Influenza 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Gastrointestinal disorders Nausea 5.0
General disorders and administration site conditions Pain 5.0
Infections and infestations Sinusitis 5.0
Infections and infestations Upper respiratory tract infection 5.0
Reproductive system and breast disorders Vaginal haemorrhage 5.0
Infections and infestations Vaginal infection 5.0
Vaginal inflammation 5.0
Reproductive system and breast disorders Vulvovaginal discomfort 5.0
Nervous system disorders Sinus headache 4.85
Reproductive system and breast disorders Breast pain 4.81
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.81
Musculoskeletal and connective tissue disorders Myalgia 4.81
General disorders and administration site conditions Asthenia 4.8
Musculoskeletal and connective tissue disorders Back pain 4.8
Infections and infestations Nasopharyngitis 4.8
Skin and subcutaneous tissue disorders Pruritus 4.8
Infections and infestations Infection
Gastrointestinal disorders Nausea
General disorders and administration site conditions Influenza like illness 4.62
Nervous system disorders Insomnia 4.62
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Asthenia
Cardiac disorders Chest pain
Gastrointestinal disorders Constipation
Gastrointestinal disorders Flatulence 4.6
Gastrointestinal disorders Gastrointestinal pain
Injury, poisoning and procedural complications Injury
Nervous system disorders Insomnia 4.6
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Cardiac disorders Oedema peripheral
Infections and infestations Pneumonia
Skin and subcutaneous tissue disorders Pruritus
Reproductive system and breast disorders Vaginal haemorrhage
Investigations Weight increased
Musculoskeletal and connective tissue disorders Neck pain 4.55
Musculoskeletal and connective tissue disorders Pain in extremity 4.55
Respiratory, thoracic and mediastinal disorders Sinus congestion 4.55
Infections and infestations Upper respiratory tract infection 4.55
Musculoskeletal and connective tissue disorders Arthropathy 4.49
Infections and infestations Bronchitis 4.49
Cardiac disorders Chest pain 4.49
Skin and subcutaneous tissue disorders Dermatitis 4.49
Cardiac disorders Dizziness 4.49
Infections and infestations Fungal infection 4.49
Endocrine disorders Hirsutism 4.49
Immune system disorders Hypersensitivity 4.49
Injury, poisoning and procedural complications Injury 4.49
Nervous system disorders Insomnia 4.49
Musculoskeletal and connective tissue disorders Osteoarthritis 4.49
Gastrointestinal disorders Pharyngitis 4.49
Infections and infestations Pneumonia 4.49
Skin and subcutaneous tissue disorders Rash 4.49
Reproductive system and breast disorders Vaginal discharge 4.49
Investigations Weight increased 4.49
Infections and infestations Sinusitis
Reproductive system and breast disorders Metrorrhagia
General disorders and administration site conditions Pain
Respiratory, thoracic and mediastinal disorders Sinus congestion
Reproductive system and breast disorders Uterine pain 4.46
Musculoskeletal and connective tissue disorders Arthropathy 4.44
General disorders and administration site conditions Asthenia 4.44
Infections and infestations Bronchitis 4.44
Respiratory, thoracic and mediastinal disorders Cough 4.44
Gastrointestinal disorders Dyspepsia 4.44
Gastrointestinal disorders Gastroenteritis 4.44
Immune system disorders Hypersensitivity 4.44
Cardiac disorders Oedema peripheral 4.44
Musculoskeletal and connective tissue disorders Osteoarthritis 4.44
Infections and infestations Pneumonia 4.44
Infections and infestations Urinary tract infection 4.44
Infections and infestations Upper respiratory tract infection 4.42
Reproductive system and breast disorders Metrorrhagia 4.41
Gastrointestinal disorders Nausea 4.41
Musculoskeletal and connective tissue disorders Arthralgia 4.35
Gastrointestinal disorders Dyspepsia 4.35
Nervous system disorders Insomnia 4.35
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.35
General disorders and administration site conditions Pain 4.35
Musculoskeletal and connective tissue disorders Pain in extremity 4.35
Investigations Weight increased 4.35
Infections and infestations Bronchitis
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Constipation 4.26
Gastrointestinal disorders Gastrointestinal pain
Vascular disorders Hypertension 4.26
Gastrointestinal disorders Nausea 4.26
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Diarrhoea 4.2
General disorders and administration site conditions Asthenia
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Flatulence
Reproductive system and breast disorders Metrorrhagia 4.1
Gastrointestinal disorders Nausea
Infections and infestations Vaginal infection
Vaginal inflammation
Infections and infestations Nasopharyngitis 4.07
Infections and infestations Nasopharyngitis 4.05
Gastrointestinal disorders Nausea 4.02
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 4.0
Musculoskeletal and connective tissue disorders Arthritis 4.0
Musculoskeletal and connective tissue disorders Back pain 4.0
Musculoskeletal and connective tissue disorders Bone pain 4.0
Reproductive system and breast disorders Breast pain
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 4.0
Immune system disorders Hypersensitivity 4.0
Nervous system disorders Insomnia 4.0
Infections and infestations Nasopharyngitis
Reproductive system and breast disorders Pruritus genital 4.0
Infections and infestations Rhinitis 4.0
Infections and infestations Sinusitis 4.0
Reproductive system and breast disorders Vaginal haemorrhage 4.0
Infections and infestations Vaginal infection 4.0
Vaginal inflammation 4.0
Musculoskeletal and connective tissue disorders Arthralgia 3.95
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.95
Musculoskeletal and connective tissue disorders Arthralgia 3.88
Gastrointestinal disorders Constipation 3.88
Nervous system disorders Insomnia 3.88
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.88
Gastrointestinal disorders Nausea 3.88
Musculoskeletal and connective tissue disorders Neck pain 3.88
Psychiatric disorders Anxiety 3.85
Gastrointestinal disorders Constipation 3.85
Investigations Weight increased 3.85
Reproductive system and breast disorders Breast pain
Psychiatric disorders Depression
General disorders and administration site conditions Hot flush
Reproductive system and breast disorders Menopausal symptoms
Musculoskeletal and connective tissue disorders Arthralgia 3.79
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.79
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Reproductive system and breast disorders Vulvovaginal discomfort
Reproductive system and breast disorders Breast tenderness
Infections and infestations Upper respiratory tract infection
Skin and subcutaneous tissue disorders Pruritus 3.6
Infections and infestations Sinusitis 3.6
Musculoskeletal and connective tissue disorders Back pain 3.57
Infections and infestations Sinusitis 3.57
Infections and infestations Upper respiratory tract infection 3.57
Infections and infestations Urinary tract infection 3.57
Infections and infestations Upper respiratory tract infection 3.52
Reproductive system and breast disorders Vaginal discharge 3.52
Psychiatric disorders Anxiety
Reproductive system and breast disorders Breast enlargement
Infections and infestations Bronchitis 3.45
Respiratory, thoracic and mediastinal disorders Cough 3.45
General disorders and administration site conditions Cyst
Psychiatric disorders Depression 3.45
Vascular disorders Hypertension
Infections and infestations Influenza 3.45
Gastrointestinal disorders Nausea
Immune system disorders Asthma 3.37
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Breast neoplasm 3.37
Gastrointestinal disorders Constipation 3.37
General disorders and administration site conditions Cyst 3.37
Gastrointestinal disorders Dyspepsia 3.37
Gastrointestinal disorders Flatulence 3.37
Infections and infestations Fungal infection 3.37
Gastrointestinal disorders Gastroenteritis 3.37
Vascular disorders Hypertension 3.37
Nervous system disorders Hypoaesthesia 3.37
Infections and infestations Infection 3.37
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.37
Musculoskeletal and connective tissue disorders Myalgia 3.37
Gastrointestinal disorders Nausea 3.37
Cardiac disorders Oedema peripheral 3.37
Ear and labyrinth disorders Otitis media 3.37
Reproductive system and breast disorders Vaginal discharge 3.37
Investigations Weight increased 3.37
Immune system disorders Asthma 3.33
Musculoskeletal and connective tissue disorders Back pain 3.33
Eye disorders Conjunctivitis 3.33
Psychiatric disorders Depression 3.33
Gastrointestinal disorders Diarrhoea 3.33
Vascular disorders Hypertension 3.33
Nervous system disorders Hypoaesthesia 3.33
Infections and infestations Infection 3.33
Infections and infestations Vaginal infection 3.33
Vaginal inflammation 3.33
Infections and infestations Vulvovaginal mycotic infection
Gastrointestinal disorders Nausea
Psychiatric disorders Depression 3.08
Infections and infestations Influenza 3.08
Musculoskeletal and connective tissue disorders Neck pain 3.08
Respiratory, thoracic and mediastinal disorders Sinus congestion 3.08
Psychiatric disorders Depression 3.03
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Arthralgia 3.0
Reproductive system and breast disorders Breast pain 3.0
Psychiatric disorders Depression 3.0
Social circumstances Family stress 3.0
Gastrointestinal disorders Flatulence 3.0
General disorders and administration site conditions Hot flush 3.0
General disorders and administration site conditions Influenza like illness 3.0
Reproductive system and breast disorders Menopausal symptoms 3.0
Reproductive system and breast disorders Metrorrhagia 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 3.0
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Pharyngitis 3.0
Skin and subcutaneous tissue disorders Pruritus 3.0
Infections and infestations Sinusitis
Infections and infestations Sinusitis 3.0
Reproductive system and breast disorders Vaginal discharge 3.0
Reproductive system and breast disorders Breast pain
Gastrointestinal disorders Dyspepsia 2.91
Ear and labyrinth disorders Ear pain 2.91
General disorders and administration site conditions Hot flush 2.91
Vascular disorders Hypertension 2.91
Reproductive system and breast disorders Menopausal symptoms 2.91
Respiratory, thoracic and mediastinal disorders Sinus congestion 2.91
Infections and infestations Vulvovaginal mycotic infection
Gastrointestinal disorders Abdominal pain 2.87
Gastrointestinal disorders Constipation
Skin and subcutaneous tissue disorders Dermatitis 2.87
Gastrointestinal disorders Diarrhoea 2.87
Cardiac disorders Dizziness
Gastrointestinal disorders Gastrointestinal pain 2.87
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Skin and subcutaneous tissue disorders Rash 2.87
Gastrointestinal disorders Nausea 2.82
Gastrointestinal disorders Abdominal distension
Infections and infestations Nasopharyngitis
Musculoskeletal and connective tissue disorders Pain in extremity
Infections and infestations Vulvovaginal candidiasis
Infections and infestations Vulvovaginal mycotic infection
Psychiatric disorders Depression
Nervous system disorders Headache
Gastrointestinal disorders Nausea 2.7
Skin and subcutaneous tissue disorders Pruritus
Gastrointestinal disorders Abdominal distension 2.68
Musculoskeletal and connective tissue disorders Pain in extremity 2.68
Reproductive system and breast disorders Reproductive tract disorder 2.68
Reproductive system and breast disorders Vaginal discharge 2.68
Gastrointestinal disorders Nausea 2.65
Reproductive system and breast disorders Reproductive tract disorder 2.65
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 2.63
Skin and subcutaneous tissue disorders Hyperaesthesia 2.63
Infections and infestations Nasopharyngitis
Gastrointestinal disorders Nausea 2.63
Reproductive system and breast disorders Nipple pain 2.63
Psychiatric disorders Anxiety
Gastrointestinal disorders Constipation
Reproductive system and breast disorders Breast tenderness 2.46
Infections and infestations Upper respiratory tract infection 2.44
Infections and infestations Vulvovaginal mycotic infection 2.44
Psychiatric disorders Nervousness 2.4
Infections and infestations Rhinitis 2.4
Psychiatric disorders Tension 2.4
Investigations Weight increased 2.4
Musculoskeletal and connective tissue disorders Arthropathy
General disorders and administration site conditions Asthenia 2.3
Reproductive system and breast disorders Breast enlargement 2.3
Eye disorders Conjunctivitis
Respiratory, thoracic and mediastinal disorders Cough
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Gastroenteritis
Immune system disorders Hypersensitivity
Nervous system disorders Hypoaesthesia
Infections and infestations Infection
Nervous system disorders Migraine
Musculoskeletal and connective tissue disorders Osteoarthritis
Ear and labyrinth disorders Otitis media
Gastrointestinal disorders Pharyngitis 2.3
Infections and infestations Urinary tract infection
General disorders and administration site conditions Influenza like illness 2.27
Psychiatric disorders Anxiety 2.25
Eye disorders Conjunctivitis 2.25
Gastrointestinal disorders Diarrhoea 2.25
Endocrine disorders Hirsutism 2.25
Immune system disorders Hypersensitivity 2.25
Infections and infestations Infection 2.25
Gastrointestinal disorders Pharyngitis 2.25
Skin and subcutaneous tissue disorders Pruritus 2.25
Infections and infestations Urinary tract infection 2.25
Reproductive system and breast disorders Breast enlargement 2.22
Cardiac disorders Chest pain 2.22
Gastrointestinal disorders Flatulence 2.22
Endocrine disorders Hirsutism 2.22
Nervous system disorders Insomnia 2.22
Nervous system disorders Migraine 2.22
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.22
Musculoskeletal and connective tissue disorders Myalgia 2.22
Ear and labyrinth disorders Otitis media 2.22
Gastrointestinal disorders Pharyngitis 2.22
Reproductive system and breast disorders Vaginal discharge 2.22
Surgical and medical procedures Vasodilation procedure 2.22
Investigations Weight increased 2.22
Reproductive system and breast disorders Metrorrhagia
Infections and infestations Genital candidiasis
Skin and subcutaneous tissue disorders Hyperaesthesia 2.11
Reproductive system and breast disorders Nipple pain 2.11
Gastrointestinal disorders Abdominal pain 2.0
Musculoskeletal and connective tissue disorders Arthritis 2.0
Musculoskeletal and connective tissue disorders Bone pain 2.0
Infections and infestations Candida infection
Social circumstances Family stress 2.0
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
General disorders and administration site conditions Hot flush 2.0
Infections and infestations Influenza 2.0
General disorders and administration site conditions Influenza like illness 2.0
Reproductive system and breast disorders Menopausal symptoms 2.0
Gastrointestinal disorders Nausea 2.0
Infections and infestations Rhinitis 2.0
Infections and infestations Urinary tract infection 2.0
Infections and infestations Vaginal infection 2.0
Vaginal inflammation 2.0
Musculoskeletal and connective tissue disorders Back pain
Skin and subcutaneous tissue disorders Pruritus
Reproductive system and breast disorders Vulvovaginal pruritus
Investigations Weight increased 1.94
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Cervical polyp
Investigations Weight increased
Reproductive system and breast disorders Breast tenderness
Reproductive system and breast disorders Metrorrhagia
Infections and infestations Sinusitis
Infections and infestations Urinary tract infection
Psychiatric disorders Anxiety 1.8
Reproductive system and breast disorders Endometrial disorder 1.8
Musculoskeletal and connective tissue disorders Arthralgia 1.79
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.79
Infections and infestations Nasopharyngitis 1.79
Gastrointestinal disorders Nausea 1.79
Reproductive system and breast disorders Vulvovaginal discomfort 1.79
Musculoskeletal and connective tissue disorders Arthralgia 1.77
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.77
Infections and infestations Nasopharyngitis 1.77
Infections and infestations Sinusitis 1.77
Reproductive system and breast disorders Uterine pain 1.77
Reproductive system and breast disorders Vaginal discharge 1.77
Psychiatric disorders Anxiety 1.72
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Breast neoplasm 1.72
Gastrointestinal disorders Constipation 1.72
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.72
Musculoskeletal and connective tissue disorders Myalgia 1.72
Cardiac disorders Oedema peripheral 1.72
Infections and infestations Urinary tract infection 1.72
Reproductive system and breast disorders Vaginal discharge 1.72
Reproductive system and breast disorders Breast tenderness
Reproductive system and breast disorders Metrorrhagia
Infections and infestations Upper respiratory tract infection
Infections and infestations Upper respiratory tract infection 1.6
Psychiatric disorders Anxiety 1.52
Gastrointestinal disorders Constipation 1.52
Nervous system disorders Insomnia 1.52
Nervous system disorders Sinus headache 1.52
Reproductive system and breast disorders Vaginal discharge 1.47
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain
Reproductive system and breast disorders Endometrial disorder
Gastrointestinal disorders Gastrointestinal pain
Infections and infestations Influenza
Psychiatric disorders Nervousness
Cardiac disorders Palpitations
Infections and infestations Sinusitis
Psychiatric disorders Tension
Musculoskeletal and connective tissue disorders Arthralgia 1.35
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.35
Musculoskeletal and connective tissue disorders Back pain
Infections and infestations Nasopharyngitis
Musculoskeletal and connective tissue disorders Arthralgia 1.32
Skin and subcutaneous tissue disorders Hyperaesthesia 1.32
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.32
Infections and infestations Nasopharyngitis 1.32
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 1.32
Reproductive system and breast disorders Nipple pain 1.32
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Infections and infestations Nasopharyngitis
Vascular disorders Hypertension
Musculoskeletal and connective tissue disorders Neck pain
Reproductive system and breast disorders Vaginal haemorrhage 1.2
Musculoskeletal and connective tissue disorders Arthralgia 1.15
Immune system disorders Asthma
Immune system disorders Asthma 1.15
Cardiac disorders Chest pain 1.15
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 1.15
Infections and infestations Fungal infection
Infections and infestations Infection 1.15
Nervous system disorders Migraine 1.15
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.15
Gastrointestinal disorders Pharyngitis
Reproductive system and breast disorders Vaginal discharge
Gastrointestinal disorders Abdominal pain 1.12
Musculoskeletal and connective tissue disorders Arthropathy 1.12
Immune system disorders Asthma 1.12
Reproductive system and breast disorders Breast enlargement 1.12
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Breast neoplasm 1.12
Cardiac disorders Chest pain 1.12
Gastrointestinal disorders Constipation 1.12
Respiratory, thoracic and mediastinal disorders Cough 1.12
Psychiatric disorders Depression 1.12
Gastrointestinal disorders Diarrhoea 1.12
Cardiac disorders Dizziness 1.12
Gastrointestinal disorders Flatulence 1.12
Gastrointestinal disorders Gastrointestinal pain 1.12
Nervous system disorders Insomnia 1.12
Musculoskeletal and connective tissue disorders Osteoarthritis 1.12
Ear and labyrinth disorders Otitis media 1.12
Infections and infestations Pneumonia 1.12
Surgical and medical procedures Vasodilation procedure 1.12
Skin and subcutaneous tissue disorders Pruritus 1.11
Musculoskeletal and connective tissue disorders Arthralgia 1.0
Reproductive system and breast disorders Breast pain 1.0
Infections and infestations Candida infection 1.0
Psychiatric disorders Depression 1.0
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 1.0
Immune system disorders Hypersensitivity 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Gastrointestinal disorders Nausea 1.0
General disorders and administration site conditions Pain 1.0
Reproductive system and breast disorders Perineal pain 1.0
Gastrointestinal disorders Pharyngitis 1.0
Infections and infestations Rhinitis
Reproductive system and breast disorders Vaginal discharge
Reproductive system and breast disorders Vaginal discharge 1.0
Reproductive system and breast disorders Uterine pain
Infections and infestations Vulvovaginitis 0.893
Musculoskeletal and connective tissue disorders Pain in extremity 0.885
Infections and infestations Urinary tract infection 0.885
Reproductive system and breast disorders Vulvovaginal discomfort 0.885
Infections and infestations Vulvovaginal mycotic infection 0.82
Skin and subcutaneous tissue disorders Hyperaesthesia 0.735
Reproductive system and breast disorders Nipple pain 0.735
Cardiac disorders Oedema peripheral 0.735
Reproductive system and breast disorders Vaginal discharge
Reproductive system and breast disorders Endometrial hyperplasia 0.704
General disorders and administration site conditions Application site reaction 0.6
Cardiac disorders Palpitations 0.6
Cardiac disorders Dizziness 0.575
Endocrine disorders Hirsutism 0.575
Immune system disorders Hypersensitivity 0.575
Infections and infestations Pneumonia 0.575
Investigations Weight increased 0.575
General disorders and administration site conditions Oedema 0.5
Gastrointestinal disorders Pharyngitis 0.5
Skin and subcutaneous tissue disorders Pruritus 0.5

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
22.99
Injury, poisoning and procedural complications
16.14
Skin and subcutaneous tissue disorders
10.97
Product issues
8.06
Reproductive system and breast disorders
7.57
Vascular disorders
6.22
Nervous system disorders
5.86
Psychiatric disorders
5.18
Gastrointestinal disorders
2.74
Investigations
2.27

Cross References

Resources Reference
CAS NUMBER 50-28-2
ChEBI 16469
ChEMBL CHEMBL135
DrugBank DB00783
DrugCentral 1057
EPA CompTox DTXSID0020573
FDA SRS 4TI98Z838E
Human Metabolome Database HMDB0000151
Guide to Pharmacology 1012
KEGG C00951
PDB EST
PharmGKB PA449503
PubChem 5757
SureChEMBL SCHEMBL8049
ZINC ZINC000013520815
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