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Identification
NameEtonogestrel
Accession NumberDB00294  (APRD00766)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionEtonogestrel is a molecule used in hormonal contraceptives, most notably the subdermal implant Implanon. [Wikipedia]
Structure
Thumb
Synonyms
3-Ketodesogestrel
3-Oxodesogestrel
Etonogestrelum
Implanon
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ImplanonImplant68 mg/1SubcutaneousOrganon USA Inc.2011-09-06Not applicableUs
NexplanonImplant68 mg/1SubcutaneousOrganon USA Inc.2006-07-17Not applicableUs
NexplanonImplant68 mg/1SubcutaneousOrganon USA Inc.2013-09-27Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
NuvaringPhysicians Total Care, Inc.
SaltsNot Available
Categories
UNII304GTH6RNH
CAS number54048-10-1
WeightAverage: 324.4565
Monoisotopic: 324.20893014
Chemical FormulaC22H28O2
InChI KeyGCKFUYQCUCGESZ-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][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
Pharmacology
IndicationFor use as a female contraceptive (depot).
Structured Indications Not Available
PharmacodynamicsEtonogestrel 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 actionEtonogestrel 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinyes
agonist
HumanP03372 details
Progesterone receptorProteinyes
agonist
HumanP06401 details
Related Articles
AbsorptionNot Available
Volume of distribution
  • 201 L
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationExcretion of ENG and its metabolites, either as free steroid or as conjugates, is mainly in urine and to a lesser extent in feces.
Half life25 hours
ClearanceNot Available
ToxicitySymptoms of overdose include nausea, vomiting, vaginal bleeding, and other menstrual irregularities.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
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
AicarThe therapeutic efficacy of Aicar 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
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
BexaroteneThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Bexarotene.Approved, 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.Approved
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
C1 Esterase Inhibitor (Human)Etonogestrel may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Etonogestrel may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
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
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
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
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
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
DexamethasoneThe serum concentration of Etonogestrel can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet 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
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
EtravirineThe serum concentration of Etonogestrel can be decreased when it is combined with Etravirine.Approved
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
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
HirulogThe therapeutic efficacy of Hirulog can be decreased when used in combination with Etonogestrel.Experimental
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 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
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
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
ModafinilThe serum concentration of Etonogestrel can be decreased when it is combined with Modafinil.Approved, Investigational
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.Investigational
NafcillinThe serum concentration of Etonogestrel can be decreased when it is combined with Nafcillin.Approved
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
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.Approved
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
ThiazolidinedioneThe therapeutic efficacy of Thiazolidinedione can be decreased when used in combination with Etonogestrel.Investigational
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
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
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
Ym150The therapeutic efficacy of Ym150 can be decreased when used in combination with Etonogestrel.Investigational
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 ReferencesNot Available
External Links
ATC CodesG03AC08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (753 KB)
MSDSNot Available
ADMET
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 )
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)
US5150718 No1992-09-292009-09-29Us
US5989581 No1998-04-082018-04-08Us
US8722037 No2007-09-282027-09-28Us
US8888745 No2006-08-282026-08-28Us
Properties
StateSolid
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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

Targets

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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
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 ]
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 isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
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 ]

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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 ]
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Drug created on June 13, 2005 07:24 / Updated on December 04, 2016 02:43