estradiol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
estrogens 1057 50-28-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • estradiol
  • 17Beta-Estradiol
  • 17Beta-Oestradiol
  • Beta-Estradiol
  • estradiol hemihydrate
The 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids.
  • Molecular weight: 272.39
  • Formula: C18H24O2
  • CLOGP: 3.78
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 2
  • TPSA: 40.46
  • ALOGS: -4.11
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 mg N
2 mg O
1 mg P
0.30 mg P
5 mg R
50 mcg TD
1 mg TD
1.53 mg TD
25 mcg V
7.50 mcg V

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.09 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.84 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 5 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 23, 1975 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Product adhesion issue 4427.56 10.01 1138 80634 3817 46600473
Hot flush 1066.85 10.01 760 81012 42757 46561533
Application site rash 810.53 10.01 263 81509 2319 46601971
Application site erythema 525.17 10.01 227 81545 4677 46599613
Application site pruritus 463.55 10.01 196 81576 3817 46600473
Product quality issue 447.60 10.01 422 81350 35226 46569064
Product physical issue 437.47 10.01 200 81572 4727 46599563
Application site irritation 392.90 10.01 140 81632 1679 46602611
Meningioma 326.10 10.01 147 81625 3358 46600932
Vulvovaginal discomfort 288.46 10.01 118 81654 2106 46602184
Wrong technique in product usage process 276.79 10.01 405 81367 54017 46550273
Application site reaction 234.85 10.01 76 81696 663 46603627
Death 218.07 10.01 162 81610 335386 46268904
Toxicity to various agents 196.81 10.01 63 81709 211703 46392587
Menopausal symptoms 194.70 10.01 85 81687 1794 46602496
Vulvovaginal pain 192.47 10.01 88 81684 2079 46602211
Pneumonia viral 165.06 10.01 117 81655 6507 46597783
Breast tenderness 156.43 10.01 77 81695 2155 46602135
Vaginal haemorrhage 156.14 10.01 208 81564 25396 46578894
Vulvovaginal burning sensation 155.46 10.01 69 81703 1517 46602773
Completed suicide 147.37 10.01 37 81735 145883 46458407
Application site pain 146.35 10.01 90 81682 3933 46600357
Vulvovaginal dryness 144.83 10.01 73 81699 2152 46602138
Blood oestrogen decreased 139.58 10.01 39 81733 192 46604098
Vaginal discharge 138.84 10.01 93 81679 4715 46599575
Fibromyalgia 126.17 10.01 228 81544 36235 46568055
Postmenopausal haemorrhage 125.07 10.01 64 81708 1949 46602341
Soft tissue disorder 120.94 10.01 81 81691 4105 46600185
Application site vesicles 116.19 10.01 55 81717 1409 46602881
Acute kidney injury 113.62 10.01 148 81624 235707 46368583
Colitis microscopic 113.06 10.01 93 81679 6463 46597827
Product complaint 112.79 10.01 122 81650 11979 46592311
Night sweats 109.44 10.01 182 81590 27068 46577222
Device material issue 107.49 10.01 29 81743 122 46604168
Incorrect dose administered by product 106.74 10.01 29 81743 126 46604164
Drug ineffective 105.09 10.01 1716 80056 676122 45928168
Application site urticaria 103.11 10.01 32 81740 240 46604050
Application site burn 99.86 10.01 42 81730 806 46603484
Migraine 99.38 10.01 309 81463 69717 46534573
Product substitution issue 96.10 10.01 125 81647 14906 46589384
Ovarian hyperstimulation syndrome 95.20 10.01 63 81709 3129 46601161
Skin reaction 89.39 10.01 103 81669 10843 46593447
Feeling abnormal 86.24 10.01 440 81332 124620 46479670
Hormone level abnormal 85.94 10.01 51 81721 2087 46602203
Febrile neutropenia 82.88 10.01 31 81741 94596 46509694
Pancytopenia 81.26 10.01 24 81748 85034 46519256
Blood cholesterol increased 80.97 10.01 201 81571 39812 46564478
Neutropenia 80.74 10.01 79 81693 143125 46461165
Skin irritation 77.80 10.01 79 81693 7208 46597082
Vaginal odour 68.75 10.01 27 81745 431 46603859
Thrombocytopenia 67.75 10.01 73 81699 126508 46477782
Glaucoma 67.52 10.01 109 81663 15812 46588478
Intentional overdose 66.43 10.01 16 81756 64928 46539362
Hyperkalaemia 64.07 10.01 7 81765 50702 46553588
Cardiac arrest 63.39 10.01 40 81732 90359 46513931
Hypotension 62.55 10.01 204 81568 232385 46371905
Exposure during pregnancy 61.79 10.01 59 81713 108153 46496137
Oestrogen receptor assay positive 60.05 10.01 24 81748 402 46603888
Vaginal infection 59.55 10.01 63 81709 6030 46598260
Insomnia 59.12 10.01 492 81280 164432 46439858
Application site hypersensitivity 58.85 10.01 20 81752 206 46604084
Thyroid disorder 58.63 10.01 88 81684 11988 46592302
Multiple organ dysfunction syndrome 58.58 10.01 10 81762 51700 46552590
Arthritis 56.77 10.01 277 81495 77039 46527251
Product availability issue 56.40 10.01 31 81741 1094 46603196
Headache 56.21 10.01 1161 80611 477191 46127099
Sepsis 56.02 10.01 95 81677 135919 46468371
Vulvovaginal pruritus 55.88 10.01 41 81731 2406 46601884
Cardio-respiratory arrest 55.19 10.01 18 81754 59851 46544439
Respiratory failure 54.94 10.01 51 81721 94765 46509525
Cardiac failure 53.85 10.01 37 81735 79911 46524379
Product dose omission issue 53.76 10.01 490 81282 168030 46436260
Product shape issue 53.07 10.01 17 81755 143 46604147
Drug abuse 51.89 10.01 23 81749 63385 46540905
Disease progression 51.86 10.01 50 81722 91250 46513040
Diverticulitis 51.75 10.01 151 81621 32888 46571402
Hysterectomy 51.59 10.01 66 81706 7740 46596550
Herpes zoster 50.43 10.01 244 81528 67628 46536662
Platelet count decreased 49.92 10.01 61 81711 99963 46504327
Vaginal erosion 49.79 10.01 12 81760 28 46604262
Application site erosion 48.94 10.01 17 81755 188 46604102
Depression 48.50 10.01 483 81289 169621 46434669
Breast pain 48.30 10.01 63 81709 7531 46596759
Progesterone receptor assay positive 48.28 10.01 19 81753 305 46603985
Pyrexia 47.10 10.01 388 81384 348414 46255876
Incorrect dose administered 46.30 10.01 180 81592 45370 46558920
Hyperhidrosis 46.17 10.01 291 81481 89017 46515273
Blood oestrogen increased 46.03 10.01 13 81759 67 46604223
Hand deformity 45.71 10.01 4 81768 34570 46569720
Oral pain 44.41 10.01 119 81653 24678 46579612
Renal failure 44.36 10.01 82 81690 113512 46490778
Overdose 44.06 10.01 69 81703 101910 46502380
Uterine haemorrhage 43.79 10.01 42 81730 3575 46600715
Breast cancer in situ 43.59 10.01 29 81743 1453 46602837
Device adhesion issue 43.36 10.01 35 81737 2367 46601923
Product packaging issue 43.31 10.01 25 81747 971 46603319
Mucosal inflammation 43.14 10.01 8 81764 38968 46565322
Septic shock 42.85 10.01 24 81748 57869 46546421
Application site scar 42.78 10.01 16 81756 222 46604068
Liver function test abnormal 41.92 10.01 177 81595 46310 46557980
Breast cancer 41.58 10.01 174 81598 45344 46558946
Application site inflammation 41.53 10.01 18 81754 373 46603917
General physical health deterioration 41.40 10.01 88 81684 115681 46488609
Breast enlargement 40.94 10.01 28 81744 1469 46602821
Application site swelling 40.88 10.01 20 81752 552 46603738
Metabolic acidosis 40.76 10.01 9 81763 38771 46565519
Wrong technique in device usage process 40.75 10.01 31 81741 1922 46602368
Application site dermatitis 40.51 10.01 15 81757 202 46604088
Lactic acidosis 39.66 10.01 6 81766 33903 46570387
Haemoglobin decreased 38.26 10.01 108 81664 128841 46475449
Drug interaction 37.88 10.01 205 81567 202889 46401401
Product odour abnormal 37.75 10.01 24 81748 1112 46603178
Blood creatinine increased 37.69 10.01 47 81725 76356 46527934
Application site discolouration 37.40 10.01 21 81751 773 46603517
Bronchitis 37.31 10.01 315 81457 105664 46498626
Maternal exposure during pregnancy 36.62 10.01 78 81694 102471 46501819
Oestradiol decreased 36.49 10.01 9 81763 24 46604266
Malignant neoplasm progression 36.35 10.01 36 81736 64890 46539400
Pneumonia 36.13 10.01 454 81318 375866 46228424
Butterfly rash 35.96 10.01 22 81750 952 46603338
Vulvovaginal mycotic infection 35.62 10.01 41 81731 4310 46599980
Sinusitis fungal 35.44 10.01 21 81751 857 46603433
Salpingo-oophorectomy unilateral 35.38 10.01 16 81756 368 46603922
Incorrect dose administered by device 35.13 10.01 34 81738 2926 46601364
Bladder prolapse 35.05 10.01 28 81744 1866 46602424
Hypothalamo-pituitary disorder 34.82 10.01 19 81753 661 46603629
Bradycardia 34.61 10.01 39 81733 66259 46538031
Fungal infection 34.47 10.01 122 81650 29398 46574892
Mood swings 34.31 10.01 83 81689 16169 46588121
Fibrocystic breast disease 34.26 10.01 23 81749 1170 46603120
Breast cancer female 34.15 10.01 47 81725 5916 46598374
Hyponatraemia 33.80 10.01 80 81692 101252 46503038
Nipple pain 33.66 10.01 14 81758 261 46604029
Dermatitis contact 33.61 10.01 55 81717 8068 46596222
Glossodynia 33.41 10.01 18 81754 44355 46559935
Endometrial cancer 32.99 10.01 31 81741 2572 46601718
Anaemia 32.91 10.01 288 81484 255491 46348799
Synovitis 32.80 10.01 201 81571 60874 46543416
Application site dryness 32.72 10.01 12 81760 157 46604133
Product packaging quantity issue 32.72 10.01 22 81750 1122 46603168
Oestradiol increased 32.58 10.01 10 81762 72 46604218
Vomiting 32.52 10.01 578 81194 452216 46152074
Gastrointestinal haemorrhage 31.87 10.01 54 81718 77319 46526971
Product size issue 31.48 10.01 15 81757 390 46603900
Renal impairment 31.48 10.01 51 81721 74321 46529969
Pleural effusion 31.40 10.01 61 81711 82891 46521399
Application site exfoliation 31.28 10.01 14 81758 314 46603976
Bone marrow failure 30.95 10.01 7 81765 29662 46574628
Hypoglycaemia 30.58 10.01 30 81742 54319 46549971
Suicide attempt 30.25 10.01 31 81741 55005 46549285
Schizoaffective disorder 30.19 10.01 23 81749 1429 46602861
Muscle spasms 29.64 10.01 338 81434 122775 46481515
Poor quality product administered 29.20 10.01 31 81741 2978 46601312
Osteopenia 28.97 10.01 80 81692 16881 46587409
Hepatic function abnormal 28.93 10.01 12 81760 34409 46569881
Cholestasis 28.75 10.01 6 81766 26887 46577403
Endometrial cancer stage I 28.69 10.01 12 81760 227 46604063
Rectal prolapse 28.60 10.01 23 81749 1547 46602743
Colitis ischaemic 28.44 10.01 58 81714 10074 46594216
Menopause 28.12 10.01 26 81746 2113 46602177
Vitamin D decreased 28.11 10.01 50 81722 7843 46596447
Endometrial stromal sarcoma 28.03 10.01 7 81765 20 46604270
Vulvovaginal injury 28.01 10.01 13 81759 318 46603972
Application site ulcer 27.98 10.01 10 81762 121 46604169
Interstitial lung disease 27.87 10.01 32 81740 53917 46550373
Breast discomfort 27.46 10.01 13 81759 333 46603957
Hypokalaemia 27.40 10.01 72 81700 87952 46516338
Ophthalmic vein thrombosis 27.12 10.01 10 81762 133 46604157
Rheumatoid arthritis 26.84 10.01 280 81492 239935 46364355
Product prescribing issue 26.84 10.01 18 81754 914 46603376
No adverse event 26.82 10.01 125 81647 34106 46570184
Pseudoprecocious puberty 26.75 10.01 5 81767 0 46604290
Hypoxia 26.50 10.01 31 81741 51807 46552483
Sputum increased 26.35 10.01 23 81749 1733 46602557
Tachycardia 26.30 10.01 88 81684 99534 46504756
International normalised ratio increased 26.24 10.01 26 81746 46857 46557433
Diaphragmatic rupture 25.97 10.01 11 81761 215 46604075
Device use issue 25.97 10.01 21 81751 1424 46602866
Uterine leiomyoma 25.93 10.01 49 81723 8050 46596240
Hepatotoxicity 25.89 10.01 6 81766 25003 46579287
Device expulsion 25.88 10.01 8 81764 27534 46576756
Dermal absorption impaired 25.87 10.01 6 81766 11 46604279
Atrial fibrillation 25.67 10.01 94 81678 103496 46500794
Dehydration 25.53 10.01 169 81603 159371 46444919
Nasal polyps 25.51 10.01 25 81747 2185 46602105
Altered state of consciousness 25.40 10.01 5 81767 23343 46580947
Fall 25.23 10.01 415 81357 328682 46275608
Placenta accreta 25.21 10.01 10 81762 164 46604126
Therapeutic product effect increased 25.21 10.01 18 81754 1012 46603278
Therapeutic response unexpected 25.05 10.01 72 81700 15544 46588746
Respiratory symptom 24.99 10.01 24 81748 2046 46602244
Cardiac failure congestive 24.94 10.01 80 81692 91670 46512620
Endometrial hyperplasia 24.66 10.01 16 81756 768 46603522
Embolism venous 24.64 10.01 26 81746 2481 46601809
Neutrophil count decreased 24.40 10.01 24 81748 43402 46560888
Carpal tunnel syndrome 24.37 10.01 72 81700 15787 46588503
Dyspareunia 24.27 10.01 25 81747 2319 46601971
Application site discomfort 24.14 10.01 12 81760 343 46603947
Anxiety 24.05 10.01 450 81322 181507 46422783
White blood cell count decreased 23.94 10.01 108 81664 112123 46492167
Endometrial hypertrophy 23.78 10.01 11 81761 267 46604023
Coma 23.78 10.01 41 81731 58308 46545982
Depressed level of consciousness 23.73 10.01 29 81743 47540 46556750
Respiratory arrest 23.64 10.01 15 81757 33801 46570489
Spinal operation 23.58 10.01 38 81734 5502 46598788
Periodontal disease 23.27 10.01 21 81751 1654 46602636
Tinnitus 23.13 10.01 103 81669 27570 46576720
Shock 23.09 10.01 5 81767 21840 46582450
Rheumatoid factor positive 23.07 10.01 4 81768 20457 46583833
Spinal stenosis 22.26 10.01 60 81712 12483 46591807
Application site discharge 22.24 10.01 9 81763 156 46604134
Abdominal distension 22.20 10.01 211 81561 73140 46531150
Systemic lupus erythematosus 22.09 10.01 51 81721 65129 46539161
Libido decreased 22.09 10.01 25 81747 2580 46601710
Pregnancy 21.95 10.01 10 81762 27127 46577163
Skin burning sensation 21.92 10.01 54 81718 10638 46593652
Influenza like illness 21.80 10.01 174 81598 57396 46546894
Histamine intolerance 21.74 10.01 6 81766 28 46604262
Injection site inflammation 21.73 10.01 27 81745 3075 46601215
Vessel puncture site bruise 21.64 10.01 11 81761 330 46603960
Delirium 21.58 10.01 20 81752 37208 46567082
Vision blurred 21.56 10.01 224 81548 79484 46524806
Dyspnoea 21.55 10.01 714 81058 514834 46089456
Sinusitis 21.54 10.01 333 81439 129435 46474855
Pericardial effusion 21.31 10.01 9 81763 25534 46578756
Breast calcifications 21.21 10.01 17 81755 1138 46603152
Decreased appetite 21.21 10.01 227 81545 193609 46410681
Oxygen saturation decreased 21.20 10.01 57 81715 69107 46535183
Normal tension glaucoma 21.15 10.01 7 81765 66 46604224
Atypical haemolytic uraemic syndrome 20.56 10.01 12 81760 476 46603814
Paraesthesia 20.51 10.01 304 81468 117133 46487157
Wound 20.41 10.01 27 81745 42775 46561515
Change of bowel habit 20.41 10.01 20 81752 1748 46602542
Breast mass 20.33 10.01 38 81734 6193 46598097
Acute respiratory failure 20.27 10.01 13 81759 29125 46575165
Pituitary tumour 20.15 10.01 15 81757 900 46603390
Sopor 20.04 10.01 5 81767 19823 46584467
Device breakage 19.92 10.01 49 81723 9643 46594647
Respiratory distress 19.90 10.01 16 81756 31900 46572390
Product colour issue 19.78 10.01 13 81759 638 46603652
Vulvovaginal erythema 19.40 10.01 9 81763 220 46604070
Alanine aminotransferase abnormal 19.33 10.01 23 81749 2504 46601786
Vaginal disorder 19.21 10.01 13 81759 670 46603620
Lung disorder 18.98 10.01 29 81743 43275 46561015
Emotional disorder 18.98 10.01 56 81716 12268 46592022
Cystocele 18.78 10.01 16 81756 1167 46603123
Breast disorder 18.76 10.01 20 81752 1931 46602359
Bone density abnormal 18.71 10.01 25 81747 3059 46601231
Irritability 18.64 10.01 100 81672 28846 46575444
Lymphogranuloma venereum 18.63 10.01 4 81768 4 46604286
Ventricular dyskinesia 18.63 10.01 8 81764 162 46604128
Rhabdomyolysis 18.43 10.01 28 81744 41881 46562409
Rectocele 18.31 10.01 14 81758 875 46603415
Drug reaction with eosinophilia and systemic symptoms 18.19 10.01 15 81757 29533 46574757
Hepatic failure 18.16 10.01 19 81753 33397 46570893
Chronic sinusitis 18.07 10.01 32 81740 5001 46599289
Palpitations 17.98 10.01 250 81522 95009 46509281
Intentional self-injury 17.91 10.01 10 81762 24156 46580134
Erythema of eyelid 17.76 10.01 19 81753 1842 46602448
Female genital tract fistula 17.75 10.01 25 81747 3214 46601076
Application site laceration 17.74 10.01 4 81768 6 46604284
Productive cough 17.74 10.01 39 81733 50676 46553614
Photosensitivity reaction 17.71 10.01 56 81716 12736 46591554
Pericarditis 17.59 10.01 10 81762 23917 46580373
Pre-existing condition improved 17.56 10.01 37 81735 6575 46597715
Weight increased 17.52 10.01 394 81378 164079 46440211
Stress 17.48 10.01 152 81620 51399 46552891
Palmar-plantar erythrodysaesthesia syndrome 17.40 10.01 7 81765 20444 46583846
Pelvic infection 17.26 10.01 9 81763 285 46604005
Peripheral swelling 17.25 10.01 380 81392 157691 46446599
Spider naevus 17.21 10.01 7 81765 123 46604167
Procedural anxiety 17.20 10.01 11 81761 515 46603775
Pneumocystis jirovecii pneumonia 17.15 10.01 3 81769 15245 46589045
Atrophic vulvovaginitis 17.11 10.01 17 81755 1511 46602779
Eczema 17.10 10.01 76 81696 20324 46583966
Bacterial vulvovaginitis 16.88 10.01 11 81761 532 46603758
Prosopagnosia 16.66 10.01 5 81767 33 46604257
Meniscus injury 16.45 10.01 34 81738 5962 46598328
Breast cancer stage I 16.42 10.01 13 81759 855 46603435
Drug resistance 16.40 10.01 5 81767 17363 46586927
Vulvovaginal inflammation 16.36 10.01 11 81761 561 46603729
Acute respiratory distress syndrome 16.35 10.01 9 81763 21913 46582377
Encephalopathy 16.21 10.01 21 81751 33568 46570722
Peritonitis 16.19 10.01 8 81764 20706 46583584
Porphyria non-acute 16.11 10.01 9 81763 328 46603962
Poor quality sleep 16.09 10.01 61 81711 15192 46589098
Craniopharyngioma 16.02 10.01 7 81765 148 46604142
Product outer packaging issue 15.87 10.01 4 81768 12 46604278
Sinus rhythm 15.80 10.01 11 81761 594 46603696
Ovarian atrophy 15.68 10.01 6 81766 89 46604201
Vulvovaginal swelling 15.66 10.01 10 81762 467 46603823
Breast cyst 15.46 10.01 16 81756 1493 46602797
Hospitalisation 15.38 10.01 58 81714 63327 46540963
Anosmia 15.37 10.01 26 81746 3918 46600372
Amnesia 15.31 10.01 125 81647 41506 46562784
Fluid overload 15.30 10.01 15 81757 27170 46577120
Product taste abnormal 15.24 10.01 18 81754 1945 46602345
Incorrect product administration duration 15.21 10.01 44 81728 9533 46594757
Sleep apnoea syndrome 15.19 10.01 78 81694 22123 46582167
Feeling hot 15.11 10.01 116 81656 37812 46566478
Uterine polyp 15.06 10.01 17 81755 1750 46602540
Arthropathy 14.95 10.01 87 81685 84613 46519677
Infusion related reaction 14.81 10.01 110 81662 101098 46503192
Ultrasound liver abnormal 14.79 10.01 4 81768 17 46604273
Expulsion of medication 14.79 10.01 4 81768 17 46604273
Neoplasm progression 14.70 10.01 15 81757 26668 46577622
Unresponsive to stimuli 14.63 10.01 21 81751 32153 46572137
Memory impairment 14.61 10.01 203 81569 77134 46527156
Diastolic dysfunction 14.51 10.01 30 81742 5262 46599028
Diarrhoea 14.38 10.01 818 80954 558784 46045506
Osteoarthritis 14.34 10.01 169 81603 61856 46542434
Acute hepatic failure 14.33 10.01 4 81768 14717 46589573
Abnormal dreams 14.23 10.01 45 81727 10234 46594056
Intestinal polyp 14.23 10.01 13 81759 1040 46603250
Tenderness 14.23 10.01 63 81709 16818 46587472
Contraindicated product administered 14.17 10.01 82 81690 79865 46524425
Low density lipoprotein increased 14.14 10.01 32 81740 5968 46598322
Breast cancer stage II 14.13 10.01 11 81761 706 46603584
Pneumonia aspiration 14.01 10.01 21 81751 31584 46572706
Gastrooesophageal reflux disease 13.98 10.01 195 81577 74149 46530141
Soft tissue swelling 13.96 10.01 12 81760 886 46603404
Application site infection 13.95 10.01 5 81767 61 46604229
Haematemesis 13.91 10.01 18 81754 28788 46575502
Disseminated intravascular coagulation 13.89 10.01 8 81764 18997 46585293
Thermal burn 13.79 10.01 28 81744 4849 46599441
Retinal vein thrombosis 13.69 10.01 9 81763 442 46603848
Periodontitis 13.66 10.01 23 81749 3453 46600837
Trans-sexualism 13.51 10.01 3 81769 4 46604286
Muscle fatigue 13.40 10.01 18 81754 2213 46602077
Sleep disorder 13.36 10.01 133 81639 46662 46557628
Product physical consistency issue 13.33 10.01 9 81763 462 46603828
Blood bilirubin increased 13.05 10.01 25 81747 34159 46570131
Poor venous access 13.03 10.01 38 81734 8270 46596020
Electrolyte imbalance 12.95 10.01 7 81765 17219 46587071
Pulmonary oedema 12.90 10.01 46 81726 51059 46553231
Product use issue 12.81 10.01 235 81537 94409 46509881
Blood oestrogen abnormal 12.76 10.01 3 81769 6 46604284
Melaena 12.76 10.01 18 81754 27754 46576536
Liver disorder 12.73 10.01 29 81743 37217 46567073
Pulmonary arterial hypertension 12.73 10.01 16 81756 25912 46578378
Plasma cell myeloma 12.63 10.01 38 81734 44440 46559850
Cor pulmonale acute 12.56 10.01 8 81764 372 46603918
Procedural pain 12.52 10.01 51 81721 13128 46591162
Oral herpes 12.49 10.01 67 81705 19323 46584967
Bladder pain 12.46 10.01 14 81758 1433 46602857
Application site nodule 12.45 10.01 3 81769 7 46604283
Breast hyperplasia 12.26 10.01 7 81765 266 46604024
Crying 12.26 10.01 71 81701 21070 46583220
Premature menopause 12.08 10.01 10 81762 701 46603589
Periorbital oedema 12.03 10.01 27 81745 5008 46599282
Gingival recession 12.01 10.01 13 81759 1277 46603013
Surgery 12.01 10.01 89 81683 28696 46575594
Seizure 11.93 10.01 148 81624 122906 46481384
Therapy non-responder 11.80 10.01 35 81737 41117 46563173
Hypogonadism 11.79 10.01 5 81767 98 46604192
Lower respiratory tract infection 11.75 10.01 53 81719 55036 46549254
Eosinophilic pleural effusion 11.70 10.01 4 81768 42 46604248
Ileus 11.66 10.01 5 81767 14059 46590231
Breast swelling 11.64 10.01 12 81760 1114 46603176
Burning sensation 11.62 10.01 124 81648 44287 46560003
Hypersensitivity 11.58 10.01 345 81427 149976 46454314
Diabetic ketoacidosis 11.51 10.01 9 81763 18201 46586089
Premature delivery 11.49 10.01 13 81759 22056 46582234
Blood pressure systolic abnormal 11.45 10.01 28 81744 5489 46598801
Aptyalism 11.44 10.01 8 81764 435 46603855
Blood pressure abnormal 11.38 10.01 47 81725 12170 46592120
Accidental overdose 11.37 10.01 11 81761 20055 46584235
Benign breast neoplasm 11.32 10.01 12 81760 1151 46603139
Endometrial disorder 11.30 10.01 9 81763 597 46603693
Foetal exposure during pregnancy 11.29 10.01 23 81749 30724 46573566
Mammogram abnormal 11.21 10.01 9 81763 604 46603686
Alanine aminotransferase increased 11.17 10.01 100 81672 88351 46515939
Diverticulum 11.15 10.01 44 81728 11162 46593128
Xanthoma 11.15 10.01 4 81768 49 46604241
Pulmonary congestion 11.14 10.01 6 81766 14793 46589497
Parotid gland enlargement 11.12 10.01 10 81762 784 46603506
Somnolence 11.11 10.01 200 81572 156321 46447969
Stress urinary incontinence 11.11 10.01 16 81756 2100 46602190
Jaundice 11.09 10.01 21 81751 28824 46575466
Product administered at inappropriate site 11.05 10.01 17 81755 2366 46601924
Thyroxine decreased 11.02 10.01 8 81764 462 46603828
Hepatocellular injury 10.91 10.01 22 81750 29500 46574790
Rash 10.87 10.01 744 81028 355768 46248522
Withdrawal bleed 10.86 10.01 5 81767 120 46604170
Urine output decreased 10.83 10.01 3 81769 11094 46593196
Intervertebral disc degeneration 10.83 10.01 49 81723 13203 46591087
Impatience 10.83 10.01 7 81765 334 46603956
Pulmonary hypertension 10.77 10.01 30 81742 35963 46568327
Hyperglycaemia 10.67 10.01 29 81743 35042 46569248
Patient dissatisfaction with treatment 10.66 10.01 4 81768 56 46604234
Ascites 10.58 10.01 31 81741 36553 46567737
Agranulocytosis 10.57 10.01 14 81758 22171 46582119
Pain in extremity 10.55 10.01 554 81218 258126 46346164
Blood testosterone decreased 10.53 10.01 4 81768 58 46604232
Endometriosis 10.52 10.01 22 81750 3888 46600402
Blister 10.49 10.01 122 81650 44509 46559781
Loss of personal independence in daily activities 10.48 10.01 58 81714 57125 46547165
Infective pulmonary exacerbation of cystic fibrosis 10.40 10.01 3 81769 10804 46593486
Road traffic accident 10.31 10.01 74 81698 23617 46580673
Low turnover osteopathy 10.25 10.01 23 81749 4266 46600024
Product prescribing error 10.15 10.01 65 81707 19982 46584308
Expired product administered 10.08 10.01 27 81745 5595 46598695
Pruritus 10.08 10.01 520 81252 241832 46362458

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Meningioma 83.23 42.42 16 666 1427 29950369
Foetal exposure during pregnancy 61.12 42.42 25 657 36846 29914950
Off label use 57.15 42.42 46 636 249244 29702552
Prolactin-producing pituitary tumour 46.79 42.42 6 676 34 29951762
Hyperprolactinaemia 43.26 42.42 9 673 1191 29950605

Pharmacologic Action:

SourceCodeDescription
ATC G03CA03 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
ESTROGENS
Natural and semisynthetic estrogens, plain
ATC G03AA14 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, fixed combinations
ATC G03AA17 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, fixed combinations
ATC G03AB08 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, sequential preparations
ATC G03CA53 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
ESTROGENS
Natural and semisynthetic estrogens, plain
ATC H01CC54 SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES
HYPOTHALAMIC HORMONES
Anti-gonadotropin-releasing hormones
FDA CS M0447348 Estradiol Congeners
FDA MoA N0000000100 Estrogen Receptor Agonists
FDA EPC N0000175825 Estrogen
MeSH PA D004967 Estrogens
MeSH PA D006728 Hormones
CHEBI has role CHEBI:50114 oestrogene
CHEBI has role CHEBI:62872 aldehyde oxidase (ec 1.2.3.1) inhibitors
CHEBI has role CHEBI:75771 mus musculus metabolite
CHEBI has role CHEBI:77746 h. sapiens metabolites
CHEBI has role CHEBI:83056 daphnia magna metabolites

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Premenstrual dysphoric disorder indication 596004
Contraception indication 13197004
Female hypogonadism syndrome indication 16041008
Atrophic vaginitis indication 52441000
Urethral atrophy indication 52620003
Primary ovarian failure indication 65846009
Acne vulgaris indication 88616000
Postmenopausal osteoporosis indication 102447009
Menopausal flushing indication 198436008
Atrophic vulva indication 248861000 DOID:14275
Advanced Prostatic Carcinoma indication
Metastatic Breast Carcinoma indication
Metastatic Prostate Carcinoma indication
Amenorrhea off-label use 14302001 DOID:13938
Polycystic ovaries off-label use 69878008
Dysmenorrhea off-label use 266599000
Postcoital contraception off-label use 268463003
Abnormal uterine bleeding unrelated to menstrual cycle off-label use 312984006
Menorrhagia off-label use 386692008
Pre-Menopausal Osteoporosis off-label use
Heart valve disorder contraindication 368009 DOID:4079
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Gynecomastia contraindication 4754008 DOID:12698
Hypocalcemia contraindication 5291005
Alcoholism contraindication 7200002
Weight gain finding contraindication 8943002
Hypercholesterolemia contraindication 13644009
Hyperkalemia contraindication 14140009
Jaundice contraindication 18165001
Toxic shock syndrome contraindication 18504008 DOID:14115
Myocardial infarction contraindication 22298006 DOID:5844
Fibroadenosis of breast contraindication 23260002 DOID:10352
Diplopia contraindication 24982008
Retinal hemorrhage contraindication 28998008
Depressive disorder contraindication 35489007
Chloasma contraindication 36209000
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Body fluid retention contraindication 43498006
Thrombosis of retinal vein contraindication 46085004
Humoral hypercalcemia of malignancy contraindication 47709007
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Dementia contraindication 52448006
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Hyperlipidemia contraindication 55822004 DOID:1168
Heart disease contraindication 56265001 DOID:114
Anorexia nervosa contraindication 56882008 DOID:8689
Benign mammary dysplasia contraindication 57993004
Acute nephropathy contraindication 58574008
Obstructive hyperbilirubinemia contraindication 59848001
Hepatic failure contraindication 59927004
Cerebrovascular disease contraindication 62914000 DOID:6713
Thrombophlebitis contraindication 64156001 DOID:3875
Osteoporosis contraindication 64859006 DOID:11476
Intermenstrual bleeding - irregular contraindication 64996003
Hypercalcemia contraindication 66931009 DOID:12678
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050847
Hyperglycemia contraindication 80394007 DOID:4195
Heart failure contraindication 84114007 DOID:6000
Epilepsy contraindication 84757009 DOID:1826
Breast lump contraindication 89164003
Kidney disease contraindication 90708001 DOID:557
Malignant neoplasm of liver contraindication 93870000 DOID:3571
Uterine leiomyoma contraindication 95315005 DOID:13223
Neoplasm of prostate contraindication 126906006 DOID:10283
Neoplasm of female genital organ contraindication 126907002 DOID:120
Deep venous thrombosis contraindication 128053003
Seizure disorder contraindication 128613002
Endometriosis contraindication 129103003
Bed-ridden contraindication 160685001
Liver function tests abnormal contraindication 166603001
Mammography abnormal contraindication 168750009
Angina pectoris contraindication 194828000
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Cholestasis of pregnancy contraindication 235888006
Metabolic syndrome X contraindication 237602007 DOID:14221
Endometrial carcinoma contraindication 254878006 DOID:2871
Benign prostatic hyperplasia contraindication 266569009
Edema contraindication 267038008
Chorea contraindication 271700006
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Osteopenia contraindication 312894000
Functional visual loss contraindication 313165001
Non-Q wave myocardial infarction contraindication 314207007
Malignant tumor of cervix contraindication 363354003 DOID:4362
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Porphyria contraindication 418470004
Resistance to activated protein C due to Factor V Leiden contraindication 421527008
Optic disc edema contraindication 423341008 DOID:146
Family history of malignant neoplasm of breast contraindication 429740004
Hypertensive urgency contraindication 443482000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002
Diabetes with Vascular Disease Complication contraindication
Breast Carcinoma in Males contraindication
Acute Thromboembolic Stroke contraindication
Major Surgery with Prolonged Post-Operative Immobilization contraindication
Nonspecific Abnormal Papanicolaou Smear of Cervix contraindication
Worsening Headache Disorder contraindication
Benign Hepatic Cell Adenoma contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.13 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.004MG IMVEXXY THERAPEUTICSMD INC N208564 May 29, 2018 RX INSERT VAGINULLL May 29, 2021 NEW PRODUCT
0.01MG IMVEXXY THERAPEUTICSMD INC N208564 May 29, 2018 RX INSERT VAGINULLL May 29, 2021 NEW PRODUCT
1MG;100MG BIJUVA THERAPEUTICSMD INC N210132 Oct. 28, 2018 RX CAPSULE ORAL Oct. 28, 2021 NEW PRODUCT
EQ 300MG BASE,1MG,0.5MG; EQ 300MG BASE ORIAHNN (COPACKAGED) ABBVIE INC N213388 May 29, 2020 RX CAPSULE ORAL May 29, 2023 NEW PRODUCT
EQ 300MG BASE,1MG,0.5MG; EQ 300MG BASE ORIAHNN (COPACKAGED) ABBVIE INC N213388 May 29, 2020 RX CAPSULE ORAL July 23, 2023 NEW CHEMICAL ENTITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Estrogen receptor Nuclear hormone receptor AGONIST EC50 10.30 WOMBAT-PK CHEMBL
Calcium-activated potassium channel subunit alpha-1 Ion channel ACTIVATOR EC50 5.60 IUPHAR
Sodium-dependent serotonin transporter Transporter Ki 5.24 DRUG MATRIX
Glucocorticoid receptor Nuclear hormone receptor Ki 4.73 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 4.93 DRUG MATRIX
Sex hormone-binding globulin Secreted Kd 8.83 CHEMBL
Steryl-sulfatase Enzyme IC50 4.08 CHEMBL
Steroid hormone receptor ERR2 Nuclear hormone receptor IC50 8.49 CHEMBL
Steroid hormone receptor ERR1 Nuclear hormone receptor IC50 8.44 CHEMBL
Androgen receptor Nuclear hormone receptor IC50 7.72 CHEMBL
G-protein coupled estrogen receptor 1 GPCR EC50 9.52 WOMBAT-PK
Estrogen receptor beta Nuclear hormone receptor EC50 9.70 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 6.54 WOMBAT-PK
Corticosteroid-binding globulin Secreted Ki 5 CHEMBL
Arachidonate 15-lipoxygenase Enzyme IC50 4.95 DRUG MATRIX
Progesterone receptor Transcription factor Ki 5.37 DRUG MATRIX
Estrogen receptor Transcription factor IC50 8.72 CHEMBL
Estrogen receptor Transcription factor IC50 8.66 CHEMBL
Estrogen receptor beta Transcription factor IC50 8.77 CHEMBL
Estrogen receptor Transcription factor IC50 9.45 CHEMBL
Androgen receptor Transcription factor IC50 6.39 CHEMBL
Estrogen receptor beta Transcription factor IC50 8.64 CHEMBL

External reference:

IDSource
4021205 VUID
N0000148651 NUI
D00105 KEGG_DRUG
35380-71-3 SECONDARY_CAS_RN
4017609 VANDF
4021205 VANDF
C0014912 UMLSCUI
CHEBI:16469 CHEBI
EST PDB_CHEM_ID
5757 PUBCHEM_CID
CHEMBL135 ChEMBL_ID
DB00783 DRUGBANK_ID
D004958 MESH_DESCRIPTOR_UI
406 INN_ID
4TI98Z838E UNII
236859 RXNORM
160774 MMSL
18201 MMSL
36188 MMSL
4684 MMSL
6157 MMSL
73244 MMSL
8602 MMSL
d00537 MMSL
001265 NDDF
007018 NDDF
116070003 SNOMEDCT_US
126172005 SNOMEDCT_US
12839006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Estring HUMAN PRESCRIPTION DRUG LABEL 1 0013-2150 RING 2 mg VAGINULLL NDA 27 sections
Alora HUMAN PRESCRIPTION DRUG LABEL 1 0023-5885 PATCH 0.03 mg TRANSDERMAL NDA 35 sections
Alora HUMAN PRESCRIPTION DRUG LABEL 1 0023-5886 PATCH 0.05 mg TRANSDERMAL NDA 35 sections
Alora HUMAN PRESCRIPTION DRUG LABEL 1 0023-5887 PATCH 0.08 mg TRANSDERMAL NDA 35 sections
Alora HUMAN PRESCRIPTION DRUG LABEL 1 0023-5888 PATCH 0.10 mg TRANSDERMAL NDA 35 sections
ELESTRIN HUMAN PRESCRIPTION DRUG LABEL 1 0037-4801 GEL, METERED 0.52 mg TOPICAL NDA 33 sections
Vivelle-Dot HUMAN PRESCRIPTION DRUG LABEL 1 0078-0343 PATCH, EXTENDED RELEASE 0.04 mg TRANSDERMAL NDA 31 sections
Vivelle-Dot HUMAN PRESCRIPTION DRUG LABEL 1 0078-0344 PATCH, EXTENDED RELEASE 0.05 mg TRANSDERMAL NDA 31 sections
Vivelle-Dot HUMAN PRESCRIPTION DRUG LABEL 1 0078-0345 PATCH, EXTENDED RELEASE 0.08 mg TRANSDERMAL NDA 31 sections
Vivelle-Dot HUMAN PRESCRIPTION DRUG LABEL 1 0078-0346 PATCH, EXTENDED RELEASE 0.10 mg TRANSDERMAL NDA 31 sections
Vivelle-Dot HUMAN PRESCRIPTION DRUG LABEL 1 0078-0365 PATCH, EXTENDED RELEASE 0.03 mg TRANSDERMAL NDA 31 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0093-3223 INSERT 10 ug VAGINULLL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0093-3541 CREAM 0.10 mg VAGINULLL ANDA 25 sections
Mimvey HUMAN PRESCRIPTION DRUG LABEL 2 0093-5455 TABLET, FILM COATED 1 mg ORAL ANDA 29 sections
Estradiol Vaginal HUMAN PRESCRIPTION DRUG LABEL 1 0115-1518 CREAM 0.10 mg VAGINULLL ANDA 23 sections
Vagifem HUMAN PRESCRIPTION DRUG LABEL 1 0169-5176 INSERT 10 ug VAGINULLL NDA 30 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-1452 TABLET 0.50 mg ORAL ANDA 22 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-1454 TABLET 1 mg ORAL ANDA 22 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-1458 TABLET 2 mg ORAL ANDA 22 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-3349 PATCH 0.03 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-3350 PATCH 0.05 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-3351 PATCH 0.08 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-3352 PATCH 0.10 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-3360 PATCH 0.04 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-3361 PATCH 0.06 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-4619 PATCH 0.03 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-4620 PATCH 0.04 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-4621 PATCH 0.05 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-4622 PATCH 0.08 mg TRANSDERMAL ANDA 29 sections
Estradiol HUMAN PRESCRIPTION DRUG LABEL 1 0378-4623 PATCH 0.10 mg TRANSDERMAL ANDA 29 sections