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Identification
NameEtonogestrel
Accession NumberDB00294  (APRD00766)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Etonogestrel 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.2013-09-27Not applicableUs
Nexplanonimplant68 mg/1subcutaneousOrganon USA Inc.2006-07-17Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
NuvaringOrganon USA Inc.
SaltsNot Available
Categories
UNII304GTH6RNH
CAS number54048-10-1
WeightAverage: 324.4565
Monoisotopic: 324.20893014
Chemical FormulaC22H28O2
InChI KeyInChIKey=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][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
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
Pharmacology
IndicationFor use as a female contraceptive (depot).
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.
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
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
Ring (slow-release)vaginal
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
SpectraNot Available
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
Interactions
Drug Interactions
Drug
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Etonogestrel.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Etonogestrel.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Etonogestrel.
AcitretinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Acitretin.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Etonogestrel.
AprepitantThe serum concentration of Etonogestrel can be decreased when it is combined with Aprepitant.
ArtemetherThe serum concentration of Etonogestrel can be decreased when it is combined with Artemether.
AtazanavirThe serum concentration of Etonogestrel can be increased when it is combined with Atazanavir.
BexaroteneThe serum concentration of Etonogestrel can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Etonogestrel can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Etonogestrel can be decreased when it is combined with Bosentan.
ButabarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Butabarbital.
ButethalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Etonogestrel may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Etonogestrel.
CarbamazepineThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Carbamazepine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Etonogestrel.
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Etonogestrel.
ClobazamThe serum concentration of Etonogestrel can be decreased when it is combined with Clobazam.
CobicistatThe serum concentration of Etonogestrel can be increased when it is combined with Cobicistat.
ColesevelamThe serum concentration of Etonogestrel can be decreased when it is combined with Colesevelam.
DabrafenibThe serum concentration of Etonogestrel can be decreased when it is combined with Dabrafenib.
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Etonogestrel.
DarunavirThe serum concentration of Etonogestrel can be decreased when it is combined with Darunavir.
DicoumarolEtonogestrel may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Etonogestrel.
EfavirenzThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Efavirenz.
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Etonogestrel.
Eslicarbazepine acetateThe serum concentration of Etonogestrel can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Etonogestrel.
ExenatideThe serum concentration of Etonogestrel can be decreased when it is combined with Exenatide.
FelbamateThe serum concentration of Etonogestrel can be decreased when it is combined with Felbamate.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Etonogestrel.
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Etonogestrel.
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.
FosaprepitantThe serum concentration of Etonogestrel can be decreased when it is combined with Fosaprepitant.
FosphenytoinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Fosphenytoin.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Etonogestrel.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Etonogestrel.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Etonogestrel.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Etonogestrel.
GriseofulvinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Griseofulvin.
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Etonogestrel.
HeptabarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Hexobarbital.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Etonogestrel.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Etonogestrel.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Etonogestrel.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Etonogestrel.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Etonogestrel.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Etonogestrel.
LamotrigineThe serum concentration of Etonogestrel can be decreased when it is combined with Lamotrigine.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Etonogestrel.
LopinavirThe serum concentration of Etonogestrel can be decreased when it is combined with Lopinavir.
LumacaftorThe serum concentration of Etonogestrel can be decreased when it is combined with Lumacaftor.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Etonogestrel.
MethohexitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Methohexital.
MetreleptinThe serum concentration of Etonogestrel can be decreased when it is combined with Metreleptin.
MifepristoneThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Mifepristone.
Mycophenolic acidThe serum concentration of Etonogestrel can be decreased when it is combined with Mycophenolic acid.
NelfinavirThe serum concentration of Etonogestrel can be decreased when it is combined with Nelfinavir.
NevirapineThe serum concentration of Etonogestrel can be decreased when it is combined with Nevirapine.
OxcarbazepineThe serum concentration of Etonogestrel can be decreased when it is combined with Oxcarbazepine.
PentobarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Pentobarbital.
PerampanelThe serum concentration of Etonogestrel can be decreased when it is combined with Perampanel.
PhenindioneThe therapeutic efficacy of Phenindione can be decreased when used in combination with Etonogestrel.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Etonogestrel.
PhenytoinThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Phenytoin.
PrimidoneThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Primidone.
PrucaloprideThe serum concentration of Etonogestrel can be decreased when it is combined with Prucalopride.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Etonogestrel.
RifabutinThe serum concentration of Etonogestrel can be decreased when it is combined with Rifabutin.
SaquinavirThe serum concentration of Etonogestrel can be decreased when it is combined with Saquinavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Etonogestrel.
SecobarbitalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Secobarbital.
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Etonogestrel.
St. John's WortThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with St. John's Wort.
SugammadexThe serum concentration of Etonogestrel can be decreased when it is combined with Sugammadex.
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Etonogestrel.
TelaprevirThe serum concentration of Etonogestrel can be decreased when it is combined with Telaprevir.
ThalidomideEtonogestrel may increase the thrombogenic activities of Thalidomide.
TipranavirThe serum concentration of Etonogestrel can be increased when it is combined with Tipranavir.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Etonogestrel.
TopiramateThe serum concentration of Etonogestrel can be decreased when it is combined with Topiramate.
Tranexamic AcidEtonogestrel may increase the thrombogenic activities of Tranexamic Acid.
TreprostinilThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Etonogestrel.
UlipristalThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Ulipristal.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Etonogestrel.
VoriconazoleThe serum concentration of Etonogestrel can be increased when it is combined with Voriconazole.
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Etonogestrel.
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.

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 May 24, 2016 02:07