ethinylestradiol ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
estrogens 1082 57-63-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ethinylestradiol betadex
  • ethynyl estradiol
  • ethinylestradiol
  • ethinyl estradiol
  • 17-ethinylestradiol
  • ethinyloestradiol
A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.
  • Molecular weight: 296.41
  • Formula: C20H24O2
  • CLOGP: 3.68
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 2
  • TPSA: 40.46
  • ALOGS: -4.64
  • ROTB: 0

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
25 mcg O
1.50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 3 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.10 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 4.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 7 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.01 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 9.70 hours Lombardo F, Berellini G, Obach RS
S (Water solubility) 0.01 mg/mL Bocci G, Oprea TI, Benet LZ

Approvals:

DateAgencyCompanyOrphan
June 25, 1943 FDA SCHERING
July 23, 2010 PMDA Bayer Yakuhin

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
Pulmonary embolism 862.97 17.88 434 12315 116250 63360023
Unintended pregnancy 678.65 17.88 172 12577 6007 63470266
Intermenstrual bleeding 589.51 17.88 162 12587 7764 63468509
Device expulsion 478.60 17.88 200 12549 34722 63441551
Deep vein thrombosis 443.59 17.88 250 12499 83550 63392723
Inappropriate schedule of product administration 339.65 17.88 228 12521 103737 63372536
No adverse event 319.41 17.88 159 12590 41246 63435027
Incorrect product administration duration 301.93 17.88 106 12643 11440 63464833
Pregnancy with contraceptive device 276.48 17.88 80 12669 4614 63471659
Product quality issue 208.50 17.88 114 12635 35751 63440522
Medical device discomfort 173.98 17.88 46 12703 1893 63474380
Heavy menstrual bleeding 154.12 17.88 74 12675 17699 63458574
Vulvovaginal discomfort 142.10 17.88 41 12708 2337 63473936
Vaginal discharge 130.23 17.88 54 12695 9144 63467129
Abortion induced 114.90 17.88 51 12698 10191 63466082
Abnormal withdrawal bleeding 97.08 17.88 16 12733 52 63476221
Cerebral venous sinus thrombosis 87.42 17.88 27 12722 1945 63474328
Device breakage 84.97 17.88 43 12706 11499 63464774
Hypercoagulation 81.79 17.88 26 12723 2059 63474214
Device failure 80.75 17.88 34 12715 5977 63470296
Thrombosis 80.36 17.88 81 12668 64674 63411599
Vulvovaginal mycotic infection 76.50 17.88 32 12717 5534 63470739
Abortion spontaneous 75.62 17.88 68 12681 47127 63429146
Ectopic pregnancy 72.58 17.88 25 12724 2542 63473731
Menstruation irregular 72.58 17.88 33 12716 6971 63469302
Product shape issue 70.92 17.88 13 12736 89 63476184
Withdrawal bleed 69.90 17.88 12 12737 53 63476220
Cervical dysplasia 67.09 17.88 25 12724 3189 63473084
Dysmenorrhoea 65.41 17.88 26 12723 3947 63472326
Vaginal haemorrhage 63.59 17.88 49 12700 27438 63448835
Menstruation delayed 61.43 17.88 20 12729 1709 63474564
Pulmonary infarction 59.66 17.88 22 12727 2725 63473548
Night sweats 55.01 17.88 58 12691 48756 63427517
Amenorrhoea 53.40 17.88 30 12719 9884 63466389
Muscle spasticity 52.93 17.88 40 12709 21754 63454519
Maternal exposure before pregnancy 52.12 17.88 27 12722 7576 63468697
Ear pain 50.03 17.88 48 12701 36070 63440203
Death 49.43 17.88 8 12741 374373 63101900
Poor quality product administered 46.26 17.88 19 12730 3137 63473136
Menstrual disorder 45.66 17.88 22 12727 5291 63470982
Transverse sinus thrombosis 44.20 17.88 12 12737 546 63475727
Smear cervix abnormal 44.08 17.88 18 12731 2928 63473345
Respiratory disorder 43.25 17.88 46 12703 39036 63437237
Cerebral thrombosis 42.17 17.88 15 12734 1676 63474597
Vena cava filter insertion 42.10 17.88 9 12740 145 63476128
Product storage error 39.79 17.88 29 12720 14927 63461346
Migraine 39.68 17.88 73 12676 103273 63373000
Body temperature increased 36.33 17.88 41 12708 37151 63439122
Toxic shock syndrome 35.10 17.88 11 12738 831 63475442
Post thrombotic syndrome 34.70 17.88 10 12739 567 63475706
Fall 34.36 17.88 18 12731 392316 63083957
Dyspareunia 33.35 17.88 14 12735 2441 63473832
Exposure during pregnancy 32.46 17.88 86 12663 155461 63320812
Complication associated with device 32.30 17.88 27 12722 16951 63459322
Papilloma viral infection 31.99 17.88 12 12737 1558 63474715
Hypomenorrhoea 30.37 17.88 9 12740 563 63475710
Cerebral venous thrombosis 28.75 17.88 12 12737 2062 63474211
Lower respiratory tract infection 28.46 17.88 74 12675 132233 63344040
Ovarian atrophy 28.28 17.88 6 12743 93 63476180
Irritable bowel syndrome 27.66 17.88 55 12694 82357 63393916
Muscle injury 27.42 17.88 48 12701 65297 63410976
Cholecystitis chronic 27.36 17.88 20 12729 10341 63465932
Uterine leiomyoma 27.15 17.88 19 12730 9179 63467094
Fungal infection 26.80 17.88 35 12714 36839 63439434
Pelvic pain 26.76 17.88 22 12727 13497 63462776
Abortion 26.61 17.88 12 12737 2484 63473789
Acute kidney injury 26.31 17.88 10 12739 263405 63212868
Folliculitis 26.14 17.88 49 12700 70268 63406005
Antiphospholipid antibodies positive 25.57 17.88 8 12741 601 63475672
Vulvovaginal burning sensation 25.26 17.88 11 12738 2098 63474175
Malaise 25.05 17.88 28 12721 415926 63060347
Product colour issue 24.97 17.88 8 12741 649 63475624
Coagulopathy 24.19 17.88 25 12724 20519 63455754
Pneumonia 24.11 17.88 34 12715 456733 63019540
Cerebrovascular accident 23.82 17.88 61 12688 107963 63368310
Superior sagittal sinus thrombosis 23.52 17.88 8 12741 783 63475490
Bacterial vulvovaginitis 23.47 17.88 8 12741 788 63475485
Unresponsive to stimuli 22.89 17.88 31 12718 33785 63442488
Vulvovaginal pain 22.52 17.88 11 12738 2724 63473549
Neutropenia 22.49 17.88 4 12745 175001 63301272
Coital bleeding 22.39 17.88 7 12742 525 63475748
Ovarian cyst 21.71 17.88 21 12728 15924 63460349
Breast tenderness 21.01 17.88 10 12739 2340 63473933
Abortion missed 20.70 17.88 9 12740 1710 63474563
Thrombocytopenia 20.44 17.88 3 12746 151154 63325119
Chlamydial infection 20.41 17.88 6 12743 365 63475908
Premenstrual syndrome 20.32 17.88 7 12742 712 63475561
Decreased appetite 19.85 17.88 13 12736 251039 63225234
Venous stent insertion 19.25 17.88 3 12746 6 63476267
Depression 19.01 17.88 84 12665 196408 63279865
Vaginal infection 18.70 17.88 14 12735 7504 63468769
Cervicitis 18.55 17.88 6 12743 502 63475771
Cough 18.39 17.88 19 12730 292724 63183549
Sinusitis 18.35 17.88 92 12657 226561 63249712
Ectropion of cervix 18.24 17.88 4 12745 73 63476200
Drug level decreased 18.05 17.88 14 12735 7905 63468368
Hypotension 17.92 17.88 17 12732 272587 63203686

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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
Pulmonary embolism 532.23 22.63 298 8960 171356 79563774
Intermenstrual bleeding 481.03 22.63 116 9142 5768 79729362
Unintended pregnancy 477.95 22.63 107 9151 3826 79731304
Device expulsion 318.93 22.63 118 9140 25743 79709387
Deep vein thrombosis 244.54 22.63 160 9098 120759 79614371
Incorrect product administration duration 217.54 22.63 73 9185 11949 79723181
Inappropriate schedule of product administration 211.42 22.63 152 9106 133476 79601654
Pregnancy with contraceptive device 208.29 22.63 54 9204 3600 79731530
Heavy menstrual bleeding 140.43 22.63 55 9203 13956 79721174
Medical device discomfort 130.09 22.63 32 9226 1722 79733408
Vulvovaginal discomfort 108.81 22.63 28 9230 1810 79733320
Abortion induced 108.42 22.63 38 9220 7071 79728059
Vaginal discharge 95.39 22.63 35 9223 7428 79727702
Product quality issue 94.07 22.63 55 9203 33885 79701245
Night sweats 74.82 22.63 56 9202 52039 79683091
Menstruation irregular 73.29 22.63 26 9232 5010 79730120
Muscle spasticity 70.82 22.63 39 9219 21436 79713694
Vulvovaginal mycotic infection 68.07 22.63 24 9234 4542 79730588
Ear pain 67.48 22.63 44 9214 32825 79702305
Menstruation delayed 66.58 22.63 18 9240 1408 79733722
Device failure 64.21 22.63 25 9233 6236 79728894
Abnormal withdrawal bleeding 63.58 22.63 10 9248 45 79735085
Cerebral venous sinus thrombosis 62.39 22.63 19 9239 2272 79732858
Vaginal haemorrhage 59.50 22.63 35 9223 21782 79713348
Withdrawal bleed 57.68 22.63 9 9249 38 79735092
Abortion spontaneous 54.53 22.63 37 9221 29470 79705660
Dysmenorrhoea 53.11 22.63 18 9240 3027 79732103
Respiratory disorder 53.06 22.63 43 9215 44813 79690317
No adverse event 51.21 22.63 39 9219 37153 79697977
Ectopic pregnancy 49.80 22.63 15 9243 1728 79733402
Hypercoagulation 49.46 22.63 17 9241 2983 79732147
Lower respiratory tract infection 48.42 22.63 67 9191 129153 79605977
Muscle injury 48.05 22.63 42 9216 48519 79686611
Body temperature increased 47.16 22.63 40 9218 44380 79690750
Cervical dysplasia 46.63 22.63 15 9243 2146 79732984
Folliculitis 45.22 22.63 43 9215 55337 79679793
Transverse sinus thrombosis 43.64 22.63 11 9247 654 79734476
Exposure during pregnancy 43.33 22.63 56 9202 101076 79634054
Acute kidney injury 43.02 22.63 5 9253 519399 79215731
Irritable bowel syndrome 42.79 22.63 44 9214 62197 79672933
Device breakage 42.55 22.63 22 9236 10653 79724477
Thrombosis 39.89 22.63 49 9209 84051 79651079
Menstrual disorder 37.36 22.63 15 9243 4052 79731078
Death 37.10 22.63 10 9248 566504 79168626
Migraine 36.78 22.63 48 9210 87445 79647685
Sinusitis 36.30 22.63 74 9184 195427 79539703
Amenorrhoea 34.00 22.63 17 9241 7675 79727455
Hypotension 32.38 22.63 6 9252 440311 79294819
Ovarian atrophy 31.81 22.63 6 9252 89 79735041
Fall 31.18 22.63 9 9249 487620 79247510
Cholecystitis chronic 29.95 22.63 17 9241 9889 79725241
Impaired healing 29.20 22.63 43 9215 87612 79647518
Cerebral venous thrombosis 28.25 22.63 11 9247 2742 79732388
Abortion missed 28.07 22.63 9 9249 1274 79733856
Blister 28.05 22.63 50 9208 119426 79615704
Complication associated with device 27.79 22.63 20 9238 17476 79717654
Uterine leiomyoma 27.77 22.63 14 9244 6429 79728701
Ill-defined disorder 27.46 22.63 36 9222 65839 79669291
Pneumonia 27.35 22.63 22 9236 660224 79074906
Sleep disorder due to general medical condition, insomnia type 26.74 22.63 29 9229 43527 79691603
Urticaria 26.32 22.63 63 9195 185138 79549992
Cerebral thrombosis 26.14 22.63 10 9248 2377 79732753
Pelvic pain 25.24 22.63 17 9241 13364 79721766
Pulmonary infarction 24.69 22.63 11 9247 3838 79731292
Ovarian failure 24.52 22.63 7 9251 669 79734461
Dyspareunia 24.43 22.63 9 9249 1929 79733201
Toxic shock syndrome 24.23 22.63 8 9250 1241 79733889
Contraindicated product administered 23.92 22.63 55 9203 157483 79577647
Neutropenia 23.22 22.63 3 9255 287707 79447423

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC G03AA01 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 G03AA02 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 G03AA03 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 G03AA04 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 G03AA05 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 G03AA06 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 G03AA07 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 G03AA08 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 G03AA09 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 G03AA10 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 G03AA11 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 G03AA12 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 G03AA13 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 G03AA15 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 G03AA16 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 G03AB01 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 G03AB02 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 G03AB03 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 G03AB04 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 G03AB05 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 G03AB06 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 G03AB07 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 G03AB09 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 G03CA01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
ESTROGENS
Natural and semisynthetic estrogens, plain
ATC L02AA03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONES AND RELATED AGENTS
Estrogens
FDA MoA N0000000100 Estrogen Receptor Agonists
CHEBI has role CHEBI:76988 xenoestrogens
MeSH PA D003270 Contraceptive Agents
MeSH PA D003271 Contraceptive Agents, Female
MeSH PA D000080066 Contraceptive Agents, Hormonal
MeSH PA D003278 Contraceptives, Oral, Hormonal
MeSH PA D004967 Estrogens
MeSH PA D006728 Hormones
MeSH PA D012102 Reproductive Control Agents
FDA EPC N0000175825 Estrogen

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Premenstrual dysphoric disorder indication 596004
Contraception indication 13197004
Atrophic vaginitis indication 52441000
Acne vulgaris indication 88616000
Postmenopausal osteoporosis indication 102447009
Menopausal flushing indication 198436008
Atrophic vulva indication 248861000 DOID:14275
Dysmenorrhea indication 266599000
Controlled ovarian stimulation indication 732970000
Amenorrhea off-label use 14302001 DOID:13938
Female hypogonadism syndrome off-label use 16041008
Polycystic ovaries off-label use 69878008
Postcoital contraception off-label use 268463003
Abnormal uterine bleeding unrelated to menstrual cycle off-label use 312984006
Menorrhagia off-label use 386692008
Heart valve disorder contraindication 368009 DOID:4079
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Hypercholesterolemia contraindication 13644009
Hyperkalemia contraindication 14140009
Jaundice contraindication 18165001
Myocardial infarction contraindication 22298006 DOID:5844
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
Dementia contraindication 52448006
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Hyperlipidemia contraindication 55822004 DOID:1168
Benign mammary dysplasia contraindication 57993004
Acute nephropathy contraindication 58574008
Obstructive hyperbilirubinemia contraindication 59848001
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Hypercalcemia contraindication 66931009 DOID:12678
Diabetes mellitus contraindication 73211009 DOID:9351
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
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
Endometrial carcinoma contraindication 254878006 DOID:2871
Benign prostatic hyperplasia contraindication 266569009
Edema contraindication 267038008
Chorea contraindication 271700006
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
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
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Porphyria contraindication 418470004
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
Nonspecific Abnormal Papanicolaou Smear of Cervix contraindication
Breast Carcinoma in Males contraindication
Major Surgery with Prolonged Post-Operative Immobilization contraindication
Diabetes with Vascular Disease Complication contraindication
Benign Hepatic Cell Adenoma contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.03MG,0.01MG;0.15MG,N/A SEASONIQUE TEVA BRANDED PHARM N021840 May 25, 2006 RX TABLET ORAL 7615545 June 15, 2023 PREVENTION OF PREGNANCY
0.02MG,0.1MG;0.01MG,N/A LOSEASONIQUE TEVA BRANDED PHARM N022262 Oct. 24, 2008 RX TABLET ORAL 7615545 June 15, 2023 PREVENTION OF PREGNANCY
0.03MG,0.01MG;0.15MG,N/A SEASONIQUE TEVA BRANDED PHARM N021840 May 25, 2006 RX TABLET ORAL 7320969 Jan. 30, 2024 PREVENTION OF PREGNANCY IN WOMEN WHO ELECT TO USE ORAL CONTRACEPTIVES AS A METHOD OF CONTRACEPTION
0.02MG,0.15MG;0.025MG,0.15MG;0.03MG,0.15MG;0.01MG,N/A QUARTETTE TEVA BRANDED PHARM N204061 March 28, 2013 RX TABLET ORAL 8450299 Oct. 7, 2025 PREVENTION OF PREGNANCY
0.02MG;0.1MG BALCOLTRA AVION PHARMS N208612 Jan. 9, 2018 RX TABLET ORAL 7838042 June 1, 2027 ADMINISTRATION OF FERROUS BISGLYCINATE TABLETS
0.03MG,0.01MG;0.15MG,N/A SEASONIQUE TEVA BRANDED PHARM N021840 May 25, 2006 RX TABLET ORAL 7855190 Dec. 5, 2028 PREVENTION OF PREGNANCY
0.02MG,0.1MG;0.01MG,N/A LOSEASONIQUE TEVA BRANDED PHARM N022262 Oct. 24, 2008 RX TABLET ORAL 7855190 Dec. 5, 2028 PREVENTION OF PREGNANCY
0.01MG,0.01MG;1MG,N/A LO LOESTRIN FE APIL N022501 Oct. 21, 2010 RX TABLET ORAL 7704984 Feb. 2, 2029 LO LOESTRIN FE IS INDICATED FOR THE PREVENTION OF PREGNANCY IN WOMEN WHO ELECT TO USE ORAL CONTRACEPTIVES AS A METHOD OF CONTRACEPTION
0.01MG,0.01MG,N/A;1MG,N/A,N/A LO MINASTRIN FE APIL N204654 July 24, 2013 DISCN TABLET, CHEWABLE, TABLET ORAL 7704984 Feb. 2, 2029 PREVENTION OF PREGNANCY
3MG,N/A;0.02MG,N/A;0.451MG,0.451MG BEYAZ BAYER HLTHCARE N022532 Sept. 24, 2010 RX TABLET ORAL 11617751 July 17, 2030 PREVENTION OF PREGNANCY
3MG,N/A;0.02MG,N/A;0.451MG,0.451MG BEYAZ BAYER HLTHCARE N022532 Sept. 24, 2010 RX TABLET ORAL 11617751 July 17, 2030 RAISE FOLATE LEVELS IN WOMEN WHO CHOOSE TO USE AN ORAL CONTRACEPTIVE AS THEIR METHOD OF CONTRACEPTION FOR THE PURPOSE OF REDUCING THE RISK OF A NEURAL TUBE DEFECT IN A PREGNANCY
3MG,N/A;0.02MG,N/A;0.451MG,0.451MG BEYAZ BAYER HLTHCARE N022532 Sept. 24, 2010 RX TABLET ORAL 11617751 July 17, 2030 TREATMENT OF MODERATE ACNE VULGARIS IN WOMEN AT LEAST 14 YEARS OF AGE IF THE PATIENT DESIRES AN ORAL CONTRACEPTIVE FOR BIRTH CONTROL
3MG,N/A;0.02MG,N/A;0.451MG,0.451MG BEYAZ BAYER HLTHCARE N022532 Sept. 24, 2010 RX TABLET ORAL 11617751 July 17, 2030 TREATMENT OF MOOD CHANGES AND/OR ANXIETY AS SYMPTOMS OF PREMENSTRUAL DYSPHORIC DISORDER (PMDD) IN WOMEN WHO CHOOSE TO USE AN ORAL CONTRACEPTIVE AS THEIR METHOD OF CONTRACEPTION
3MG,N/A;0.03MG,N/A;0.451MG,0.451MG SAFYRAL BAYER HLTHCARE N022574 Dec. 16, 2010 RX TABLET ORAL 11617751 July 17, 2030 PREVENTION OF PREGNANCY
3MG,N/A;0.03MG,N/A;0.451MG,0.451MG SAFYRAL BAYER HLTHCARE N022574 Dec. 16, 2010 RX TABLET ORAL 11617751 July 17, 2030 RAISE FOLATE LEVELS IN WOMEN WHO CHOOSE TO USE AN ORAL CONTRACEPTIVE AS THEIR METHOD OF CONTRACEPTION FOR THE PURPOSE OF REDUCING THE RISK OF A NEURAL TUBE DEFECT IN A PREGNANCY
0.013MG/24HR;0.15MG/24HR ANNOVERA MAYNE PHARMA N209627 Aug. 10, 2018 RX RING VAGINAL 10632066 Feb. 1, 2039 METHOD OF CONTRACEPTION BY INSERTING A VAGINAL SYSTEM FOR UP TO 13 21/7-DAY (IN/OUT) CYCLES, WHEREIN EFFICACY REQUIRES THE SYSTEM CANNOT BE OUT OF THE VAGINA FOR MORE THAN 2 CUMULATIVE HOURS IN ANY SUCH CYCLE WITHOUT USING ALTERNATIVE CONTRACEPTION
0.013MG/24HR;0.15MG/24HR ANNOVERA MAYNE PHARMA N209627 Aug. 10, 2018 RX RING VAGINAL 10632066 Feb. 1, 2039 METHOD OF PREVENTING PREGNANCY BY INSERTING A VAGINAL SYSTEM CONTAINING 103 MG OF SEGESTERONE ACETATE AND 17.4 MG ETHINYL ESTRADIOL INTO A VAGINA FOR UP TO THIRTEEN 21/7-DAY (IN/OUT) CYCLES
0.013MG/24HR;0.15MG/24HR ANNOVERA MAYNE PHARMA N209627 Aug. 10, 2018 RX RING VAGINAL 10765628 Feb. 1, 2039 METHOD OF CONTRACEPTION BY INSERTING A VAGINAL SYSTEM FOR UP TO 13 21/7-DAY (IN/OUT) CYCLES, WHEREIN EFFICACY REQUIRES THE SYSTEM CANNOT BE OUT OF THE VAGINA FOR MORE THAN 2 CUMULATIVE HOURS IN ANY SUCH CYCLE WITHOUT USING ALTERNATIVE CONTRACEPTION
0.013MG/24HR;0.15MG/24HR ANNOVERA MAYNE PHARMA N209627 Aug. 10, 2018 RX RING VAGINAL 10765628 Feb. 1, 2039 METHOD OF PREVENTING PREGNANCY BY INSERTING A VAGINAL SYSTEM CONTAINING 103 MG OF SEGESTERONE ACETATE AND 17.4 MG ETHINYL ESTRADIOL INTO A VAGINA FOR UP TO THIRTEEN 21/7-DAY (IN/OUT) CYCLES
0.013MG/24HR;0.15MG/24HR ANNOVERA MAYNE PHARMA N209627 Aug. 10, 2018 RX RING VAGINAL 10780047 Feb. 1, 2039 METHOD OF CONTRACEPTION BY INSERTING A VAGINAL SYSTEM FOR UP TO 13 21/7-DAY (IN/OUT) CYCLES, WHEREIN EFFICACY REQUIRES THE SYSTEM CANNOT BE OUT OF THE VAGINA FOR MORE THAN 2 CUMULATIVE HOURS IN ANY SUCH CYCLE WITHOUT USING ALTERNATIVE CONTRACEPTION
0.013MG/24HR;0.15MG/24HR ANNOVERA MAYNE PHARMA N209627 Aug. 10, 2018 RX RING VAGINAL 10780047 Feb. 1, 2039 METHOD OF PREVENTING PREGNANCY BY INSERTING A VAGINAL SYSTEM CONTAINING 103 MG OF SEGESTERONE ACETATE AND 17.4 MG ETHINYL ESTRADIOL INTO A VAGINA FOR UP TO THIRTEEN 21/7-DAY (IN/OUT) CYCLES

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.03MG/24HR;0.12MG/24HR TWIRLA AGILE N204017 Feb. 14, 2020 RX SYSTEM TRANSDERMAL Feb. 14, 2023 NEW PRODUCT
0.02MG;0.1MG TYBLUME EXELTIS USA INC N209405 March 30, 2020 RX TABLET ORAL March 30, 2023 NEW DOSAGE FORM
0.013MG/24HR;0.15MG/24HR ANNOVERA MAYNE PHARMA N209627 Aug. 10, 2018 RX RING VAGINAL Aug. 10, 2023 NEW CHEMICAL ENTITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Estrogen receptor Nuclear hormone receptor AGONIST Kd 9.83 WOMBAT-PK CHEMBL
Nuclear receptor subfamily 1 group I member 3 Nuclear hormone receptor IC50 5.52 CHEMBL
Mu-type opioid receptor GPCR Ki 4.96 DRUG MATRIX
Adenosine receptor A2a GPCR Ki 4.93 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 7.54 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 6.02 DRUG MATRIX
Aldehyde oxidase Enzyme IC50 6.24 WOMBAT-PK
Glucocorticoid receptor Nuclear hormone receptor Ki 6.11 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.35 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 4.73 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 4.99 DRUG MATRIX
Androgen receptor Nuclear hormone receptor IC50 7.30 WOMBAT-PK
Estrogen receptor beta Nuclear hormone receptor IC50 8.09 CHEMBL
Sex hormone-binding globulin Secreted Kd 6.81 CHEMBL
Solute carrier family 22 member 2 Transporter IC50 5.66 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 4.68 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 4.69 CHEMBL
Proton-coupled amino acid transporter 1 Transporter INHIBITOR IC50 4.60 IUPHAR
Androgen receptor Transcription factor IC50 5.09 CHEMBL
Arachidonate 15-lipoxygenase Enzyme IC50 5.25 DRUG MATRIX
Progesterone receptor Transcription factor Ki 6.86 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 5.88 DRUG MATRIX

External reference:

IDSource
423D2T571U UNII
4018022 VUID
N0000146366 NUI
D00554 KEGG_DRUG
4018022 VANDF
C0015011 UMLSCUI
CHEBI:4903 CHEBI
3WF PDB_CHEM_ID
CHEMBL691 ChEMBL_ID
5991 PUBCHEM_CID
DB00977 DRUGBANK_ID
D004997 MESH_DESCRIPTOR_UI
437 INN_ID
7071 IUPHAR_LIGAND_ID
4124 RXNORM
4698 MMSL
72166 MMSL
d00229 MMSL
001286 NDDF
126097006 SNOMEDCT_US
15432003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
NuvaRing HUMAN PRESCRIPTION DRUG LABEL 2 0052-0273 INSERT, EXTENDED RELEASE 0.02 mg VAGINAL NDA 28 sections
Jinteli HUMAN PRESCRIPTION DRUG LABEL 2 0093-3122 TABLET 5 ug ORAL ANDA 29 sections
Etonogestrel and Ethinyl Estradiol HUMAN PRESCRIPTION DRUG LABEL 2 0093-7679 INSERT, EXTENDED RELEASE 0.02 mg VAGINAL ANDA 29 sections
Etonogestrel and Ethinyl Estradiol HUMAN PRESCRIPTION DRUG LABEL 2 0093-7679 INSERT, EXTENDED RELEASE 0.02 mg VAGINAL ANDA 29 sections
XULANE HUMAN PRESCRIPTION DRUG LABEL 2 0378-3340 PATCH 35 ug TRANSDERMAL ANDA 28 sections
XULANE HUMAN PRESCRIPTION DRUG LABEL 2 0378-3340 PATCH 35 ug TRANSDERMAL ANDA 28 sections
NORETHINDRONE ACETATE AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 2 0378-7274 TABLET 0.03 mg ORAL ANDA 15 sections
NORETHINDRONE ACETATE AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 2 0378-7274 TABLET 0.03 mg ORAL ANDA 15 sections
NORETHINDRONE ACETATE AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 2 0378-7280 TABLET 0.02 mg ORAL ANDA 15 sections
femhrt HUMAN PRESCRIPTION DRUG LABEL 2 0430-0145 TABLET 2.50 ug ORAL NDA 33 sections
Amethyst HUMAN PRESCRIPTION DRUG LABEL 2 0480-3472 TABLET 20 ug ORAL ANDA 24 sections
Amethyst HUMAN PRESCRIPTION DRUG LABEL 2 0480-3472 TABLET 20 ug ORAL ANDA 24 sections
Nortrel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9009 TABLET 0.04 mg ORAL ANDA 21 sections
Nortrel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9009 TABLET 0.04 mg ORAL ANDA 21 sections
Junel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9025 TABLET 20 ug ORAL ANDA 15 sections
Junel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9025 TABLET 20 ug ORAL ANDA 15 sections
Junel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9025 TABLET 20 ug ORAL ANDA 15 sections
Junel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9027 TABLET 30 ug ORAL ANDA 15 sections
Junel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9027 TABLET 30 ug ORAL ANDA 15 sections
Junel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9027 TABLET 30 ug ORAL ANDA 15 sections
Levonorgestrel and Ethinyl Estradiol HUMAN PRESCRIPTION DRUG LABEL 2 0591-0295 TABLET 20 ug ORAL ANDA 24 sections
ZAFEMY HUMAN PRESCRIPTION DRUG LABEL 2 42291-930 PATCH 35 ug TRANSDERMAL ANDA 31 sections
NUVARING HUMAN PRESCRIPTION DRUG LABEL 2 50090-1008 INSERT, EXTENDED RELEASE 0.02 mg VAGINAL NDA 27 sections
XULANE HUMAN PRESCRIPTION DRUG LABEL 2 50090-1683 PATCH 35 ug TRANSDERMAL ANDA 29 sections
XULANE HUMAN PRESCRIPTION DRUG LABEL 2 50090-1683 PATCH 35 ug TRANSDERMAL ANDA 29 sections
NUVARING HUMAN PRESCRIPTION DRUG LABEL 2 50090-5611 INSERT, EXTENDED RELEASE 0.02 mg VAGINAL NDA 28 sections
NUVARING HUMAN PRESCRIPTION DRUG LABEL 2 50090-5611 INSERT, EXTENDED RELEASE 0.02 mg VAGINAL NDA 28 sections
Etonogestrel/Ethinyl Estradiol HUMAN PRESCRIPTION DRUG LABEL 2 50090-5959 INSERT, EXTENDED RELEASE 0.02 mg VAGINAL NDA AUTHORIZED GENERIC 29 sections
ANNOVERA HUMAN PRESCRIPTION DRUG LABEL 2 50261-313 RING 17.40 mg VAGINAL NDA 32 sections
ANNOVERA HUMAN PRESCRIPTION DRUG LABEL 2 50261-313 RING 17.40 mg VAGINAL NDA 32 sections