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

Stem definitionDrug idCAS RN
steroids, progestogens 1110 54048-10-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • etonogestrel
  • implanon
  • 3-Oxodesogestrel
metabolite of DESOGESTREL; structure given in first source; Implanon: implant containing etonogestrel (3-keto-desogestrel)
  • Molecular weight: 324.46
  • Formula: C22H28O2
  • CLOGP: 3.35
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 37.30
  • ALOGS: -4.64
  • ROTB: 1

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
68 mcg s.c. implant

ADMET properties:

PropertyValueReference
BA (Bioavailability) 76 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.51 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.01 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 2.87 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2 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) 25 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 3, 2001 FDA

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
Incorrect product administration duration 6268.17 49.57 1098 8651 1397 2346939
Complication associated with device 6106.76 49.57 1108 8641 1961 2346375
No adverse event 4530.36 49.57 1048 8701 8480 2339856
Device difficult to use 3540.96 49.57 617 9132 708 2347628
Unintended pregnancy 3163.57 49.57 629 9120 2122 2346214
Metrorrhagia 3139.40 49.57 604 9145 1625 2346711
Inappropriate schedule of product administration 2925.34 49.57 777 8972 11427 2336909
Pulmonary embolism 2921.07 49.57 844 8905 17239 2331097
Device expulsion 2810.65 49.57 578 9171 2402 2345934
Device breakage 2735.26 49.57 513 9236 1134 2347202
Pregnancy with implant contraceptive 2306.16 49.57 374 9375 143 2348193
Menstruation irregular 2287.41 49.57 441 9308 1190 2347146
Device deployment issue 2108.69 49.57 363 9386 354 2347982
Menorrhagia 1971.13 49.57 447 9302 3159 2345177
Product quality issue 1904.68 49.57 542 9207 10287 2338049
Device dislocation 1869.86 49.57 422 9327 2906 2345430
Deep vein thrombosis 1735.89 49.57 525 9224 12407 2335929
Amenorrhoea 1628.13 49.57 351 9398 1888 2346448
Complication of device removal 1148.51 49.57 201 9548 232 2348104
Implant site pain 1082.96 49.57 192 9557 253 2348083
Medical device removal 1061.08 49.57 191 9558 291 2348045
Weight increased 978.57 49.57 394 9355 21943 2326393
Abortion spontaneous 894.43 49.57 322 9427 13123 2335213
Vaginal haemorrhage 884.54 49.57 252 9497 4728 2343608
Pregnancy with contraceptive device 783.41 49.57 165 9584 769 2347567
Device kink 579.88 49.57 104 9645 152 2348184
Complication of device insertion 567.17 49.57 111 9638 325 2348011
Abortion induced 552.14 49.57 161 9588 3275 2345061
Dysmenorrhoea 537.12 49.57 116 9633 621 2347715
Maternal exposure before pregnancy 492.01 49.57 111 9638 749 2347587
Menstruation delayed 482.37 49.57 95 9654 290 2348046
Migraine 478.97 49.57 192 9557 10461 2337875
Headache 472.05 49.57 378 9371 79801 2268535
General anaesthesia 465.52 49.57 75 9674 23 2348313
Vaginal discharge 423.43 49.57 100 9649 845 2347491
Abnormal withdrawal bleeding 398.56 49.57 63 9686 10 2348326
Medical device discomfort 394.46 49.57 81 9668 323 2348013
Pain in extremity 383.92 49.57 260 9489 42280 2306056
Mood swings 374.05 49.57 118 9631 3151 2345185
Depression 371.68 49.57 219 9530 27913 2320423
Product storage error 359.85 49.57 125 9624 4535 2343801
Menstrual disorder 354.11 49.57 87 9662 882 2347454
Haemorrhage 345.84 49.57 154 9595 10885 2337451
Surgery 342.52 49.57 126 9623 5409 2342927
Implant site pruritus 335.82 49.57 59 9690 70 2348266
Exposure during pregnancy 329.52 49.57 195 9554 25024 2323312
Vulvovaginal discomfort 314.19 49.57 71 9678 482 2347854
Adverse event 312.96 49.57 129 9620 7530 2340806
Thrombosis 310.40 49.57 135 9614 9009 2339327
Intentional medical device removal by patient 302.90 49.57 51 9698 36 2348300
Hypomenorrhoea 286.60 49.57 53 9696 101 2348235
Implant site scar 275.89 49.57 46 9703 28 2348308
Medical device site discomfort 269.72 49.57 44 9705 18 2348318
Hypercoagulation 268.62 49.57 58 9691 309 2348027
Implant site fibrosis 266.97 49.57 43 9706 13 2348323
Ovarian cyst 266.89 49.57 81 9668 1892 2346444
Ectopic pregnancy 265.69 49.57 66 9683 702 2347634
Acne 263.77 49.57 90 9659 3086 2345250
Muscle spasms 258.85 49.57 158 9591 21408 2326928
Anxiety 256.16 49.57 176 9573 29183 2319153
Hypoaesthesia 252.63 49.57 152 9597 20063 2328273
Expired product administered 241.11 49.57 68 9681 1216 2347120
Pregnancy on contraceptive 231.30 49.57 50 9699 268 2348068
Menstruation normal 225.50 49.57 37 9712 17 2348319
Pulmonary infarction 219.26 49.57 52 9697 447 2347889
Polymenorrhoea 215.29 49.57 46 9703 231 2348105
Chest pain 213.64 49.57 155 9594 27982 2320354
Nausea 201.34 49.57 281 9468 111908 2236428
Abdominal pain 200.84 49.57 162 9587 34212 2314124
Back pain 199.50 49.57 156 9593 31503 2316833
Vena cava filter insertion 198.56 49.57 34 9715 30 2348306
Implant site infection 196.39 49.57 43 9706 247 2348089
Cervical dysplasia 195.27 49.57 51 9698 672 2347664
Implant site erythema 193.60 49.57 37 9712 91 2348245
Menometrorrhagia 193.03 49.57 41 9708 199 2348137
Coagulopathy 186.42 49.57 68 9681 2841 2345495
Chlamydial infection 183.45 49.57 35 9714 85 2348251
Product shape issue 178.67 49.57 31 9718 32 2348304
Withdrawal bleed 175.99 49.57 30 9719 25 2348311
Vulvovaginal mycotic infection 172.20 49.57 48 9701 820 2347516
Discomfort 164.65 49.57 73 9676 5086 2343250
Cerebral venous sinus thrombosis 158.35 49.57 38 9711 345 2347991
Abortion 157.70 49.57 45 9704 840 2347496
Breast pain 154.68 49.57 49 9700 1322 2347014
Product administration error 152.78 49.57 64 9685 3879 2344457
Fungal infection 152.24 49.57 68 9681 4821 2343515
Pelvic pain 149.23 49.57 52 9697 1897 2346439
Smear cervix abnormal 149.13 49.57 35 9714 286 2348050
Implant site swelling 146.79 49.57 29 9720 90 2348246
Breast tenderness 146.59 49.57 39 9710 554 2347782
Implant site bruising 142.91 49.57 26 9723 43 2348293
Product use issue 140.30 49.57 87 9662 12082 2336254
Oligomenorrhoea 138.08 49.57 31 9718 203 2348133
Incorrect route of product administration 137.27 49.57 65 9684 5271 2343065
Cerebrovascular accident 136.90 49.57 104 9645 20082 2328254
Maternal exposure during pregnancy 136.25 49.57 92 9657 14771 2333565
Infertility female 132.81 49.57 29 9720 164 2348172
Mood altered 128.36 49.57 51 9698 2695 2345641
Product use in unapproved indication 126.39 49.57 79 9670 11121 2337215
Poor quality product administered 124.84 49.57 37 9712 793 2347543
Cerebral venous thrombosis 118.77 49.57 31 9718 407 2347929
Vaginal infection 117.53 49.57 36 9713 866 2347470
Device failure 115.82 49.57 42 9707 1723 2346613
Implant site reaction 115.55 49.57 23 9726 75 2348261
Product colour issue 115.10 49.57 27 9722 220 2348116
Female sterilisation 111.29 49.57 23 9726 95 2348241
Pain 110.50 49.57 155 9594 61702 2286634
Uterine leiomyoma 106.01 49.57 38 9711 1507 2346829
Urinary tract infection 105.06 49.57 106 9643 29836 2318500
Vulvovaginal pain 102.66 49.57 28 9721 439 2347897
Weight decreased 102.40 49.57 102 9647 28269 2320067
Thrombectomy 102.24 49.57 20 9729 58 2348278
Thrombophlebitis superficial 102.23 49.57 31 9718 720 2347616
Product dose omission 95.13 49.57 113 9636 38144 2310192
Anticoagulation drug level below therapeutic 93.82 49.57 20 9729 99 2348237
Off label use 92.83 49.57 157 9592 73441 2274895
Papilloma viral infection 92.52 49.57 24 9725 307 2348029
Product prescribing error 91.57 49.57 41 9708 2919 2345417
Polycystic ovaries 91.43 49.57 22 9727 202 2348134
Libido decreased 90.12 49.57 26 9723 505 2347831
Gastrooesophageal reflux disease 87.38 49.57 58 9691 9037 2339299
Embolism venous 87.01 49.57 23 9726 318 2348018
Dizziness 85.96 49.57 134 9615 58531 2289805
Overdose 85.88 49.57 79 9670 19828 2328508
Abdominal pain lower 85.58 49.57 39 9710 2894 2345442
Pulmonary mass 83.87 49.57 34 9715 1892 2346444
Scar 80.60 49.57 33 9716 1884 2346452
Device embolisation 79.19 49.57 13 9736 6 2348330
Swelling 78.64 49.57 69 9680 16281 2332055
Hypertension 78.40 49.57 87 9662 27274 2321062
Vulvovaginal burning sensation 77.51 49.57 22 9727 402 2347934
Dyspareunia 77.36 49.57 22 9727 405 2347931
Implant site irritation 75.23 49.57 14 9735 28 2348308
Cholecystectomy 75.18 49.57 30 9719 1602 2346734
Accidental underdose 75.05 49.57 19 9730 219 2348117
Coital bleeding 74.11 49.57 16 9733 85 2348251
Emotional disorder 73.28 49.57 32 9717 2145 2346191
Dysfunctional uterine bleeding 73.24 49.57 18 9731 182 2348154
Tonsillectomy 72.40 49.57 19 9730 255 2348081
Implant site inflammation 72.25 49.57 14 9735 38 2348298
Vulvovaginal swelling 71.98 49.57 17 9732 143 2348193
Alopecia 71.88 49.57 75 9674 21926 2326410
Iron deficiency anaemia 71.13 49.57 31 9718 2068 2346268
Syncope 70.89 49.57 66 9683 16809 2331527
Obesity 69.94 49.57 28 9721 1508 2346828
Paraesthesia 69.85 49.57 74 9675 22014 2326322
Rhinitis allergic 68.81 49.57 23 9726 737 2347599
Uterine dilation and curettage 68.08 49.57 18 9731 249 2348087
Pregnancy 67.56 49.57 47 9702 7902 2340434
Asthma 67.32 49.57 54 9695 11260 2337076
Device physical property issue 66.52 49.57 17 9732 204 2348132
Bacterial vaginosis 66.39 49.57 16 9733 148 2348188
Infertility 66.29 49.57 16 9733 149 2348187
Caesarean section 65.00 49.57 36 9713 4045 2344291
Uterine haemorrhage 64.47 49.57 22 9727 752 2347584
Superior sagittal sinus thrombosis 64.22 49.57 16 9733 172 2348164
Fatigue 64.13 49.57 146 9603 84727 2263609
Bipolar disorder 63.40 49.57 25 9724 1293 2347043
Endometriosis 62.10 49.57 21 9728 698 2347638
Muscle strain 60.32 49.57 23 9726 1086 2347250
Antiphospholipid antibodies positive 58.94 49.57 14 9735 121 2348215
Breast cancer female 58.68 49.57 24 9725 1366 2346970
Drug interaction 57.85 49.57 77 9672 29086 2319250
Bacterial vulvovaginitis 57.29 49.57 14 9735 138 2348198
Vulvovaginal candidiasis 57.09 49.57 17 9732 370 2347966
Implant site cellulitis 56.39 49.57 10 9739 13 2348323
Post thrombotic syndrome 55.84 49.57 13 9736 102 2348234
Implant site paraesthesia 55.65 49.57 9 9740 3 2348333
Hormone level abnormal 54.53 49.57 17 9732 434 2347902
Seizure 53.83 49.57 68 9681 24398 2323938
Implant site necrosis 53.64 49.57 9 9740 6 2348330
Leukocytosis 52.75 49.57 30 9719 3546 2344790
Road traffic accident 52.65 49.57 32 9717 4276 2344060
Thrombophlebitis 52.59 49.57 19 9730 770 2347566
Pleuritic pain 52.26 49.57 18 9731 633 2347703
Limb discomfort 51.61 49.57 29 9720 3350 2344986
Vitamin D deficiency 50.13 49.57 22 9727 1492 2346844
Venous stent insertion 49.80 49.57 9 9740 14 2348322
Contusion 49.77 49.57 48 9701 12762 2335574
Endometrial ablation 49.67 49.57 11 9738 67 2348269

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

Pharmacologic Action:

SourceCodeDescription
ATC G03AC08 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens
FDA Chemical/Ingredient N0000011301 Progesterone Congeners
FDA EPC N0000175602 Progestin
CHEBI has role CHEBI:49323 contraceptive drug
CHEBI has role CHEBI:49324 female contraceptive drug
MeSH PA D003270 Contraceptive Agents
MeSH PA D003271 Contraceptive Agents, Female
MeSH PA D000080066 Contraceptive Agents, Hormonal
MeSH PA D012102 Reproductive Control Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Contraception indication 13197004
Heart valve disorder contraindication 368009 DOID:4079
Hypercholesterolemia contraindication 13644009
Toxic shock syndrome contraindication 18504008 DOID:14115
Myocardial infarction contraindication 22298006 DOID:5844
Diplopia contraindication 24982008
Retinal hemorrhage contraindication 28998008
Depressive disorder contraindication 35489007
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Body fluid retention contraindication 43498006
Thrombosis of retinal vein contraindication 46085004
Chronic heart failure contraindication 48447003
Dementia contraindication 52448006
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Hyperlipidemia contraindication 55822004 DOID:1168
Cerebrovascular disease contraindication 62914000 DOID:6713
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Diabetes mellitus contraindication 73211009 DOID:9351
Kidney disease contraindication 90708001 DOID:557
Malignant neoplasm of liver contraindication 93870000 DOID:3571
Deep venous thrombosis contraindication 128053003
Seizure disorder contraindication 128613002
Bed-ridden contraindication 160685001
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Pulmonary thromboembolism contraindication 233935004
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
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
Non-Q wave myocardial infarction contraindication 314207007
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
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
Hypertensive urgency contraindication 443482000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002
Worsening Headache Disorder contraindication
Major Surgery with Prolonged Post-Operative Immobilization contraindication
Diabetes with Vascular Disease Complication contraindication
Benign Hepatic Cell Adenoma contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.93 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
68MG/IMPLANT IMPLANON ORGANON USA INC N021529 July 17, 2006 DISCN IMPLANT IMPLANTATION 9757552 July 28, 2030 PREVENTION OF PREGNANCY
68MG/IMPLANT NEXPLANON ORGANON USA INC N021529 May 31, 2011 RX IMPLANT IMPLANTATION 9757552 July 28, 2030 PREVENTION OF PREGNANCY

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Progesterone receptor Nuclear hormone receptor AGONIST WOMBAT-PK CHEMBL
Estrogen receptor Nuclear hormone receptor WOMBAT-PK
Sex hormone-binding globulin Secreted Kd 8.23 CHEMBL

External reference:

IDSource
4021294 VUID
N0000179018 NUI
C0047683 UMLSCUI
D04104 KEGG_DRUG
304GTH6RNH UNII
6832 INN_ID
326451000 SNOMEDCT_US
396050000 SNOMEDCT_US
14584 RXNORM
d04772 MMSL
16189 MMSL
4021294 VANDF
007906 NDDF
CHEMBL1531 ChEMBL_ID
DB00294 DRUGBANK_ID
CHEBI:50777 CHEBI
6917715 PUBCHEM_CID
CHEMBL1697750 ChEMBL_ID
7590 IUPHAR_LIGAND_ID
C044815 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
IMPLANON HUMAN PRESCRIPTION DRUG LABEL 1 0052-0272 IMPLANT 68 mg SUBCUTANEOUS NDA 18 sections
NuvaRing HUMAN PRESCRIPTION DRUG LABEL 2 0052-0273 INSERT, EXTENDED RELEASE 0.12 mg VAGINAL NDA 20 sections
Nexplanon HUMAN PRESCRIPTION DRUG LABEL 1 0052-4330 IMPLANT 68 mg SUBCUTANEOUS NDA 19 sections
NUVARING HUMAN PRESCRIPTION DRUG LABEL 2 50090-1008 INSERT, EXTENDED RELEASE 0.12 mg VAGINAL NDA 21 sections
NuvaRing HUMAN PRESCRIPTION DRUG LABEL 2 54868-4832 INSERT, EXTENDED RELEASE 11.70 mg VAGINAL NDA 13 sections
EluRyng HUMAN PRESCRIPTION DRUG LABEL 2 65162-469 RING 0.12 mg VAGINAL ANDA 20 sections
Etonogestrel/Ethinyl Estradiol HUMAN PRESCRIPTION DRUG LABEL 2 66993-605 INSERT, EXTENDED RELEASE 11.70 mg VAGINAL NDA AUTHORIZED GENERIC 21 sections
NuvaRing HUMAN PRESCRIPTION DRUG LABEL 2 76413-131 INSERT, EXTENDED RELEASE 0.12 mg VAGINAL NDA 20 sections