Identification

Name
Etonogestrel
Accession Number
DB00294  (APRD00766)
Type
Small Molecule
Groups
Approved, Investigational
Description

Etonogestrel is a molecule used in hormonal contraceptives, most notably the subdermal implant Implanon.

Structure
Thumb
Synonyms
  • 3-Ketodesogestrel
  • 3-Oxodesogestrel
  • Etonogestrel
  • étonogestrel
  • Etonogestrelum
External IDs
ORG 3236 / ORG-3236
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ImplanonImplant68 mg/1SubcutaneousOrganon2011-09-06Not applicableUs
NexplanonImplant68 mg/1SubcutaneousOrganon2006-07-17Not applicableUs
NexplanonImplant68 mg/1SubcutaneousOrganon2013-09-27Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
NuvaRingEtonogestrel (11.7 mg/1) + Ethinyl Estradiol (2.7 mg/1)Insert, extended releaseVaginalPhysicians Total Care, Inc.2011-11-04Not applicableUs
NuvaRingEtonogestrel (.12 mg/d) + Ethinyl Estradiol (.015 mg/d)Insert, extended releaseVaginalA S Medication Solutions2001-10-032017-06-20Us
NuvaringEtonogestrel (11.4 mg) + Ethinyl Estradiol (2.6 mg)RingVaginalMerck Ltd.2004-12-02Not applicableCanada
NuvaRingEtonogestrel (.12 mg/d) + Ethinyl Estradiol (.015 mg/d)Insert, extended releaseVaginalOrganon2001-10-03Not applicableUs
NuvaRingEtonogestrel (.12 mg/d) + Ethinyl Estradiol (.015 mg/d)Insert, extended releaseVaginalCentral Texas Community Health Centers2001-10-03Not applicableUs
Categories
UNII
304GTH6RNH
CAS number
54048-10-1
Weight
Average: 324.4565
Monoisotopic: 324.20893014
Chemical Formula
C22H28O2
InChI Key
GCKFUYQCUCGESZ-BPIQYHPVSA-N
InChI
InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
IUPAC Name
(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILES
[H][[email protected]@]12CC[[email protected]@](O)(C#C)[[email protected]@]1(CC)CC(=C)[[email protected]]1([H])[[email protected]@]3([H])CCC(=O)C=C3CC[[email protected]@]21[H]

Pharmacology

Indication

For use as a female contraceptive (depot).

Structured Indications
Not Available
Pharmacodynamics

Etonogestrel is used as a female contraceptive. Etonogestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Etonogestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.

Mechanism of action

Etonogestrel binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like etonogestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.

TargetActionsOrganism
AProgesterone receptor
agonist
Human
AEstrogen receptor alpha
agonist
Human
Absorption
Not Available
Volume of distribution
  • 201 L
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination

Excretion of ENG and its metabolites, either as free steroid or as conjugates, is mainly in urine and to a lesser extent in feces.

Half life

25 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include nausea, vomiting, vaginal bleeding, and other menstrual irregularities.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Etonogestrel.Investigational
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Etonogestrel.Approved
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Etonogestrel.Approved, Investigational
AcenocoumarolEtonogestrel may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Etonogestrel.Withdrawn
AcitretinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Adapalene.Approved
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Etonogestrel.Experimental
AlitretinoinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Alitretinoin.Approved, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Etonogestrel.Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Etonogestrel.Approved
AmiodaroneThe metabolism of Etonogestrel can be decreased when combined with Amiodarone.Approved, Investigational
AmobarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Amobarbital.Approved, Illicit
AncrodThe therapeutic efficacy of Ancrod can be decreased when used in combination with Etonogestrel.Investigational
Antithrombin III humanThe therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Etonogestrel.Approved
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Etonogestrel.Approved
AprepitantThe serum concentration of Etonogestrel can be decreased when it is combined with Aprepitant.Approved, Investigational
ArdeparinThe therapeutic efficacy of Ardeparin can be decreased when used in combination with Etonogestrel.Approved, Withdrawn
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Etonogestrel.Approved, Investigational
ArtemetherThe serum concentration of Etonogestrel can be decreased when it is combined with Artemether.Approved
AtazanavirThe serum concentration of Etonogestrel can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Etonogestrel can be decreased when combined with Atomoxetine.Approved
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Etonogestrel.Investigational
BarbexacloneThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Barbital.Illicit
BecaplerminThe therapeutic efficacy of Becaplermin can be decreased when used in combination with Etonogestrel.Approved, Investigational
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Etonogestrel.Investigational
BexaroteneThe serum concentration of Etonogestrel can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Etonogestrel.Approved, Investigational
BoceprevirThe serum concentration of Etonogestrel can be increased when it is combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Etonogestrel can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Etonogestrel can be decreased when it is combined with Bosentan.Approved, Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Etonogestrel.Withdrawn
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Etonogestrel.Approved
CarbamazepineThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Carbamazepine.Approved, Investigational
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Etonogestrel.Experimental
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Etonogestrel.Experimental
CeritinibThe serum concentration of Etonogestrel can be increased when it is combined with Ceritinib.Approved
CertoparinThe therapeutic efficacy of Certoparin can be decreased when used in combination with Etonogestrel.Approved
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Etonogestrel.Approved
CholestyramineThe serum concentration of Etonogestrel can be decreased when it is combined with Cholestyramine.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Etonogestrel.Experimental
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Etonogestrel.Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Etonogestrel can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Etonogestrel can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Etonogestrel can be decreased when it is combined with Clobazam.Approved, Illicit
ClorindioneEtonogestrel may decrease the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Etonogestrel can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Etonogestrel can be increased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Etonogestrel can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Etonogestrel can be decreased when it is combined with Colestipol.Approved
Conestat alfaEtonogestrel may increase the thrombogenic activities of Conestat alfa.Approved
ConivaptanThe serum concentration of Etonogestrel can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Etonogestrel can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Etonogestrel can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Etonogestrel.Approved
DabrafenibThe serum concentration of Etonogestrel can be decreased when it is combined with Dabrafenib.Approved
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Etonogestrel.Approved
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Etonogestrel.Approved, Withdrawn
DarexabanThe therapeutic efficacy of Darexaban can be decreased when used in combination with Etonogestrel.Investigational
DarunavirThe serum concentration of Etonogestrel can be decreased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Etonogestrel can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Etonogestrel can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Etonogestrel can be decreased when combined with Delavirdine.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Etonogestrel.Investigational
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Etonogestrel.Approved
DextranThe therapeutic efficacy of Dextran can be decreased when used in combination with Etonogestrel.Approved, Vet Approved
Dextran 40The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Etonogestrel.Approved
Dextran 70The therapeutic efficacy of Dextran 70 can be decreased when used in combination with Etonogestrel.Approved
Dextran 75The therapeutic efficacy of Dextran 75 can be decreased when used in combination with Etonogestrel.Approved
DicoumarolEtonogestrel may decrease the anticoagulant activities of Dicoumarol.Approved
DihydroergotamineThe metabolism of Etonogestrel can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Etonogestrel can be decreased when combined with Diltiazem.Approved
DiphenadioneEtonogestrel may decrease the anticoagulant activities of Diphenadione.Experimental
DoxycyclineThe metabolism of Etonogestrel can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Etonogestrel can be decreased when combined with Dronedarone.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Etonogestrel.Approved
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Etonogestrel.Approved, Vet Approved
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Etonogestrel.Approved
EfavirenzThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Efavirenz.Approved, Investigational
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Etonogestrel.Approved
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Etonogestrel.Approved
EnzalutamideThe serum concentration of Etonogestrel can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Etonogestrel can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Etonogestrel can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateEtonogestrel may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideThe serum concentration of Etonogestrel can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Etonogestrel can be decreased when it is combined with Felbamate.Approved
Ferulic acidThe therapeutic efficacy of Ferulic acid can be decreased when used in combination with Etonogestrel.Experimental
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Etonogestrel.Approved
FluconazoleThe metabolism of Etonogestrel can be decreased when combined with Fluconazole.Approved
FluindioneEtonogestrel may decrease the anticoagulant activities of Fluindione.Investigational
FluvoxamineThe metabolism of Etonogestrel can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxThe therapeutic efficacy of Fondaparinux can be decreased when used in combination with Etonogestrel.Investigational
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Etonogestrel.Approved, Investigational
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Etonogestrel resulting in a loss in efficacy.Approved
FosaprepitantThe serum concentration of Etonogestrel can be decreased when it is combined with Fosaprepitant.Approved
FosphenytoinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Etonogestrel can be increased when it is combined with Fusidic Acid.Approved
GabexateThe therapeutic efficacy of Gabexate can be decreased when used in combination with Etonogestrel.Investigational
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Etonogestrel.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Etonogestrel.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Etonogestrel.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Etonogestrel.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Etonogestrel.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Etonogestrel.Approved
GriseofulvinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Griseofulvin.Approved, Vet Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Etonogestrel.Investigational
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Etonogestrel.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Hexobarbital.Approved
Human C1-esterase inhibitorEtonogestrel may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
IdelalisibThe serum concentration of Etonogestrel can be increased when it is combined with Idelalisib.Approved
IdraparinuxThe therapeutic efficacy of Idraparinux can be decreased when used in combination with Etonogestrel.Investigational
ImatinibThe metabolism of Etonogestrel can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Etonogestrel can be decreased when combined with Indinavir.Approved
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Etonogestrel.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Etonogestrel.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Etonogestrel.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Etonogestrel.Approved
Insulin HumanThe therapeutic efficacy of Insulin Human can be decreased when used in combination with Etonogestrel.Approved, Investigational
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Etonogestrel.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Etonogestrel.Approved
IsavuconazoniumThe metabolism of Etonogestrel can be decreased when combined with Isavuconazonium.Approved, Investigational
IsotretinoinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Isotretinoin.Approved
IsradipineThe metabolism of Etonogestrel can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Etonogestrel can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Etonogestrel can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Etonogestrel can be decreased when combined with Ketoconazole.Approved, Investigational
LamotrigineThe serum concentration of Etonogestrel can be decreased when it is combined with Lamotrigine.Approved, Investigational
LepirudinThe therapeutic efficacy of Lepirudin can be decreased when used in combination with Etonogestrel.Approved
LetaxabanThe therapeutic efficacy of Letaxaban can be decreased when used in combination with Etonogestrel.Investigational
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Etonogestrel.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Etonogestrel.Approved
LopinavirThe serum concentration of Etonogestrel can be decreased when it is combined with Lopinavir.Approved
LovastatinThe metabolism of Etonogestrel can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Etonogestrel can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Etonogestrel can be decreased when it is combined with Lumacaftor.Approved
MelagatranThe therapeutic efficacy of Melagatran can be decreased when used in combination with Etonogestrel.Experimental
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Etonogestrel.Approved
MethohexitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Methylphenobarbital.Approved
MetreleptinThe serum concentration of Etonogestrel can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe serum concentration of Etonogestrel can be increased when it is combined with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Etonogestrel.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Etonogestrel.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Etonogestrel.Approved, Investigational
MitotaneThe serum concentration of Etonogestrel can be decreased when it is combined with Mitotane.Approved
Mycophenolic acidThe serum concentration of Etonogestrel can be decreased when it is combined with Mycophenolic acid.Approved
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Etonogestrel.Approved
NafamostatThe therapeutic efficacy of Nafamostat can be decreased when used in combination with Etonogestrel.Approved, Investigational
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Etonogestrel.Approved, Investigational
NefazodoneThe metabolism of Etonogestrel can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Etonogestrel can be decreased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Etonogestrel can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Etonogestrel can be decreased when it is combined with Nevirapine.Approved
NilotinibThe metabolism of Etonogestrel can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Etonogestrel can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Etonogestrel can be increased when it is combined with Osimertinib.Approved
OtamixabanThe therapeutic efficacy of Otamixaban can be decreased when used in combination with Etonogestrel.Investigational
OxcarbazepineThe serum concentration of Etonogestrel can be decreased when it is combined with Oxcarbazepine.Approved
PalbociclibThe serum concentration of Etonogestrel can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Etonogestrel can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe therapeutic efficacy of Pentosan Polysulfate can be decreased when used in combination with Etonogestrel.Approved
PerampanelThe serum concentration of Etonogestrel can be decreased when it is combined with Perampanel.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Etonogestrel.Approved, Withdrawn
PhenindioneEtonogestrel may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Etonogestrel can be increased when combined with Phenobarbital.Approved
PhenprocoumonEtonogestrel may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Etonogestrel.Approved, Investigational
PosaconazoleThe metabolism of Etonogestrel can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Etonogestrel.Approved, Investigational
PrimidoneThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Primidone.Approved, Vet Approved
Protein CThe therapeutic efficacy of Protein C can be decreased when used in combination with Etonogestrel.Approved
Protein S humanThe therapeutic efficacy of Protein S human can be decreased when used in combination with Etonogestrel.Approved
ProtocatechualdehydeThe therapeutic efficacy of Protocatechualdehyde can be decreased when used in combination with Etonogestrel.Approved
PrucaloprideThe serum concentration of Etonogestrel can be decreased when it is combined with Prucalopride.Approved
RanolazineThe metabolism of Etonogestrel can be decreased when combined with Ranolazine.Approved, Investigational
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Etonogestrel.Approved, Investigational
ReviparinThe therapeutic efficacy of Reviparin can be decreased when used in combination with Etonogestrel.Approved
RifabutinThe metabolism of Etonogestrel can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Etonogestrel can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Etonogestrel can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Etonogestrel can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Etonogestrel.Approved
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Etonogestrel.Approved, Investigational
SaquinavirThe serum concentration of Etonogestrel can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Etonogestrel.Approved
SecobarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Etonogestrel.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Etonogestrel can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Etonogestrel can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Etonogestrel can be increased when it is combined with Simeprevir.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Etonogestrel.Approved, Investigational
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Etonogestrel.Investigational
St. John's WortThe serum concentration of Etonogestrel can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Etonogestrel can be increased when it is combined with Stiripentol.Approved
SugammadexThe serum concentration of Etonogestrel can be decreased when it is combined with Sugammadex.Approved
SulfisoxazoleThe metabolism of Etonogestrel can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Etonogestrel.Approved, Investigational
TelaprevirThe serum concentration of Etonogestrel can be decreased when it is combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Etonogestrel can be decreased when combined with Telithromycin.Approved
ThalidomideEtonogestrel may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Thiopental.Approved, Vet Approved
TiclopidineThe metabolism of Etonogestrel can be decreased when combined with Ticlopidine.Approved
TioclomarolEtonogestrel may decrease the anticoagulant activities of Tioclomarol.Experimental
TipranavirThe serum concentration of Etonogestrel can be increased when it is combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Etonogestrel can be decreased when it is combined with Tocilizumab.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Etonogestrel.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Etonogestrel.Approved
TopiramateThe serum concentration of Etonogestrel can be decreased when it is combined with Topiramate.Approved
Tranexamic AcidEtonogestrel may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Etonogestrel.Withdrawn
TroxerutinThe therapeutic efficacy of Troxerutin can be decreased when used in combination with Etonogestrel.Investigational
UlipristalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Ulipristal.Approved
VenlafaxineThe metabolism of Etonogestrel can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Etonogestrel can be decreased when combined with Verapamil.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Etonogestrel.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Etonogestrel.Approved, Investigational
VoriconazoleThe serum concentration of Etonogestrel can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinEtonogestrel may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Etonogestrel.Approved, Investigational, Withdrawn
ZiprasidoneThe metabolism of Etonogestrel can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
  • Take at the same time everyday.
  • Take with food.

References

Synthesis Reference

Klaus Nickisch, "METHODS FOR THE PREPARATION OF ETONOGESTREL AND DESOGESTREL." U.S. Patent US20130123523, issued May 16, 2013.

US20130123523
General References
Not Available
External Links
Human Metabolome Database
HMDB14439
PubChem Compound
6917715
PubChem Substance
46505321
ChemSpider
5292944
BindingDB
50423516
ChEBI
50777
ChEMBL
CHEMBL1531
Therapeutic Targets Database
DAP000855
PharmGKB
PA164771231
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Etonogestrel
ATC Codes
G03AC08 — Etonogestrel
AHFS Codes
  • 68:12.00 — Contraceptives
FDA label
Download (753 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentContraception1
2Not Yet RecruitingTreatmentContraception / HIV / AIDS1
2TerminatedTreatmentBenign Prostatic Hyperplasia (BPH)1
3CompletedPreventionContraception3
3RecruitingPreventionFamily Planning / Postpartum Contraception1
4Active Not RecruitingPreventionContraception1
4Active Not RecruitingTreatmentSickle Cell Disorders1
4CompletedBasic ScienceContraception1
4CompletedPreventionContinuation Rate of Contraceptive Implant1
4CompletedPreventionContraception2
4CompletedTreatmentContraception2
4CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentEndometriosis1
4Not Yet RecruitingPreventionHealthy, Reproductive Age Women / Post coital contraception1
4RecruitingPreventionBacterial Vaginosis (BV)1
4RecruitingPreventionBacterial Vaginosis (BV) / Human Immunodeficiency Virus (HIV)1
4TerminatedNot AvailableInfertilities1
4Unknown StatusDiagnosticHaemorrhage1
4Unknown StatusTreatmentBacterial Vaginosis (BV)1
4Unknown StatusTreatmentMenstrual Problem1
Not AvailableActive Not RecruitingNot AvailableContraceptive Behavior / Opiate Addiction / Pregnancy / Sexual Behavior1
Not AvailableCompletedNot AvailableAbortion; Induced / Medical Abortion, Complete or Unspecified, Without Complication1
Not AvailableCompletedNot AvailableContraception1
Not AvailableCompletedNot AvailableContraceptive Usage / Vaginal Epithelial Disruption1
Not AvailableCompletedNot AvailableHormonal Contraception1
Not AvailableCompletedNot AvailablePharmacokinetics1
Not AvailableCompletedNot AvailablePregnancy1
Not AvailableCompletedHealth Services ResearchOvarian Follicle1
Not AvailableCompletedTreatmentContraception1
Not AvailableCompletedTreatmentContraception: Optional Applicator for Insertion of Vaginal Ring1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentHypermenorrhea1
Not AvailableRecruitingNot AvailableFemale Sexual Function1
Not AvailableTerminatedPreventionAdolescents Seeking Contraception / Contraception Desired1
Not AvailableTerminatedTreatmentIn-Vitro Fertilization / Infertilities1

Pharmacoeconomics

Manufacturers
  • Organon usa inc
Packagers
Dosage forms
FormRouteStrength
ImplantSubcutaneous68 mg/1
Insert, extended releaseVaginal
RingVaginal
Prices
Unit descriptionCostUnit
Implanon 68 mg implant714.34USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5150718No1992-09-292009-09-29Us
US5989581No1998-04-082018-04-08Us
US8722037No2007-09-282027-09-28Us
US8888745No2006-08-282026-08-28Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00737 mg/mLALOGPS
logP3.19ALOGPS
logP3.6ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)17.99ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity96.35 m3·mol-1ChemAxon
Polarizability37.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9437
Caco-2 permeable+0.8167
P-glycoprotein substrateSubstrate0.6699
P-glycoprotein inhibitor IInhibitor0.6143
P-glycoprotein inhibitor IINon-inhibitor0.8387
Renal organic cation transporterNon-inhibitor0.7587
CYP450 2C9 substrateNon-substrate0.8195
CYP450 2D6 substrateNon-substrate0.9147
CYP450 3A4 substrateSubstrate0.7187
CYP450 1A2 substrateNon-inhibitor0.8898
CYP450 2C9 inhibitorNon-inhibitor0.8939
CYP450 2D6 inhibitorNon-inhibitor0.9224
CYP450 2C19 inhibitorInhibitor0.8755
CYP450 3A4 inhibitorNon-inhibitor0.7496
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5624
Ames testNon AMES toxic0.9091
CarcinogenicityNon-carcinogens0.9281
BiodegradationNot ready biodegradable0.9864
Rat acute toxicity2.1164 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8206
hERG inhibition (predictor II)Non-inhibitor0.7741
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Delta-4-steroid / Cyclohexenone / Ynone / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, 3-oxo steroid, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:50777)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Macpherson AM, Archer DF, Leslie S, Charnock-Jones DS, Makkink WK, Smith SK: The effect of etonogestrel on VEGF, oestrogen and progesterone receptor immunoreactivity and endothelial cell number in human endometrium. Hum Reprod. 1999 Dec;14(12):3080-7. [PubMed:10601100]
  2. Charnock-Jones DS, Macpherson AM, Archer DF, Leslie S, Makkink WK, Sharkey AM, Smith SK: The effect of progestins on vascular endothelial growth factor, oestrogen receptor and progesterone receptor immunoreactivity and endothelial cell density in human endometrium. Hum Reprod. 2000 Aug;15 Suppl 3:85-95. [PubMed:11041225]
  3. Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [PubMed:15063480]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2017 09:35