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Not Available
Identification
NameGestodene
Accession NumberDB06730
TypeSmall Molecule
GroupsApproved
DescriptionGestodene is a progestogen hormonal contraceptive. Products containing gestoden include Meliane, which contains 20 mcg of ethinylestradiol and 75 mcg of gestodene; and Gynera, which contains 30 mcg of ethinylestradiol and 75 mcg of gestodene.
Structure
Thumb
Synonyms
Gestoden
Gestodene
Gestodeno
Gestodenum
SH b 331
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1664P6E6MI
CAS number60282-87-3
WeightAverage: 310.4299
Monoisotopic: 310.193280076
Chemical FormulaC21H26O2
InChI KeySIGSPDASOTUPFS-XUDSTZEESA-N
InChI
InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
IUPAC Name
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,12-dien-5-one
SMILES
CC[C@]12CC[[email protected]]3[C@@H](CCC4=CC(=O)CC[[email protected]]34)[C@@H]1C=C[C@@]2(O)C#C
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
Related Articles
Absorptionin vitro 99% using 3H=R5020 / in vivo similar to progesterone
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life16 to 18 hrs.
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
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 Gestodene.Approved
AcenocoumarolGestodene may decrease the anticoagulant activities of Acenocoumarol.Approved
AcitretinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Adapalene.Approved
AlitretinoinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Alitretinoin.Approved, Investigational
AmobarbitalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Amobarbital.Approved, Illicit
AncrodThe therapeutic efficacy of Ancrod can be decreased when used in combination with Gestodene.Investigational
Antithrombin III humanThe therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Gestodene.Approved
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Gestodene.Approved
AprepitantThe serum concentration of Gestodene can be decreased when it is combined with Aprepitant.Approved, Investigational
ArdeparinThe therapeutic efficacy of Ardeparin can be decreased when used in combination with Gestodene.Approved, Withdrawn
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Gestodene.Approved, Investigational
ArtemetherThe serum concentration of Gestodene can be decreased when it is combined with Artemether.Approved
AtazanavirThe serum concentration of Gestodene can be increased when it is combined with Atazanavir.Approved, Investigational
BarbexacloneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Barbital.Illicit
BecaplerminThe therapeutic efficacy of Becaplermin can be decreased when used in combination with Gestodene.Approved, Investigational
BexaroteneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Bexarotene.Approved, Investigational
BexaroteneThe serum concentration of Gestodene can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Gestodene.Approved, Investigational
BoceprevirThe serum concentration of Gestodene can be increased when it is combined with Boceprevir.Approved
BosentanThe serum concentration of Gestodene can be decreased when it is combined with Bosentan.Approved, Investigational
C1 Esterase Inhibitor (Human)Gestodene may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Gestodene may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
CarbamazepineThe therapeutic efficacy of Gestodene can be decreased when used in combination with Carbamazepine.Approved, Investigational
CertoparinThe therapeutic efficacy of Certoparin can be decreased when used in combination with Gestodene.Approved
CholestyramineThe serum concentration of Gestodene can be decreased when it is combined with Cholestyramine.Approved
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Gestodene.Nutraceutical, Vet Approved
ClobazamThe serum concentration of Gestodene can be decreased when it is combined with Clobazam.Approved, Illicit
CobicistatThe serum concentration of Gestodene can be increased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Gestodene can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Gestodene can be decreased when it is combined with Colestipol.Approved
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Gestodene.Approved
DabrafenibThe serum concentration of Gestodene can be decreased when it is combined with Dabrafenib.Approved
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Gestodene.Approved
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Gestodene.Approved, Withdrawn
DarunavirThe serum concentration of Gestodene can be decreased when it is combined with Darunavir.Approved
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Gestodene.Approved
DextranThe therapeutic efficacy of Dextran can be decreased when used in combination with Gestodene.Approved, Vet Approved
Dextran 40The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Gestodene.Approved
Dextran 70The therapeutic efficacy of Dextran 70 can be decreased when used in combination with Gestodene.Approved
Dextran 75The therapeutic efficacy of Dextran 75 can be decreased when used in combination with Gestodene.Approved
DicoumarolGestodene may decrease the anticoagulant activities of Dicoumarol.Approved
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Gestodene.Approved, Vet Approved
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Gestodene.Approved
EfavirenzThe serum concentration of Gestodene can be decreased when it is combined with Efavirenz.Approved, Investigational
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Gestodene.Approved
Eslicarbazepine acetateThe serum concentration of Gestodene can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateGestodene may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideThe serum concentration of Gestodene can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Gestodene can be decreased when it is combined with Felbamate.Approved
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Gestodene.Approved
FluindioneGestodene may decrease the anticoagulant activities of Fluindione.Investigational
FondaparinuxThe therapeutic efficacy of Fondaparinux can be decreased when used in combination with Gestodene.Investigational
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Gestodene.Approved, Investigational
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Gestodene resulting in a loss in efficacy.Approved
FosaprepitantThe serum concentration of Gestodene can be decreased when it is combined with Fosaprepitant.Approved
FosphenytoinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Fosphenytoin.Approved
GabexateThe therapeutic efficacy of Gabexate can be decreased when used in combination with Gestodene.Investigational
GriseofulvinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Griseofulvin.Approved, Vet Approved
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Gestodene.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Hexobarbital.Approved
HirulogThe therapeutic efficacy of Hirulog can be decreased when used in combination with Gestodene.Experimental
idraparinuxThe therapeutic efficacy of idraparinux can be decreased when used in combination with Gestodene.Investigational
IsotretinoinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Isotretinoin.Approved
LamotrigineThe serum concentration of Gestodene can be decreased when it is combined with Lamotrigine.Approved, Investigational
LepirudinThe therapeutic efficacy of Lepirudin can be decreased when used in combination with Gestodene.Approved
LopinavirThe serum concentration of Gestodene can be decreased when it is combined with Lopinavir.Approved
LumacaftorThe serum concentration of Gestodene can be decreased when it is combined with Lumacaftor.Approved
MethohexitalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Methylphenobarbital.Approved
MetreleptinThe serum concentration of Gestodene can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Mifepristone.Approved, Investigational
Mycophenolic acidThe serum concentration of Gestodene can be decreased when it is combined with Mycophenolic acid.Approved
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Gestodene.Approved
NafamostatThe therapeutic efficacy of Nafamostat can be decreased when used in combination with Gestodene.Investigational
NelfinavirThe serum concentration of Gestodene can be decreased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Gestodene can be decreased when it is combined with Nevirapine.Approved
OtamixabanThe therapeutic efficacy of Otamixaban can be decreased when used in combination with Gestodene.Investigational
OxcarbazepineThe serum concentration of Gestodene can be decreased when it is combined with Oxcarbazepine.Approved
PentobarbitalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe therapeutic efficacy of Pentosan Polysulfate can be decreased when used in combination with Gestodene.Approved
PerampanelThe serum concentration of Gestodene can be decreased when it is combined with Perampanel.Approved
PhenindioneGestodene may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Phenobarbital.Approved
PhenprocoumonGestodene may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PrimidoneThe therapeutic efficacy of Gestodene 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 Gestodene.Approved
Protein S humanThe therapeutic efficacy of Protein S human can be decreased when used in combination with Gestodene.Approved
ProtocatechualdehydeThe therapeutic efficacy of Protocatechualdehyde can be decreased when used in combination with Gestodene.Approved
PrucaloprideThe serum concentration of Gestodene can be decreased when it is combined with Prucalopride.Approved
ReviparinThe therapeutic efficacy of Reviparin can be decreased when used in combination with Gestodene.Approved
RifabutinThe serum concentration of Gestodene can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Gestodene can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Gestodene can be decreased when it is combined with Rifapentine.Approved
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Gestodene.Approved
SaquinavirThe serum concentration of Gestodene can be decreased when it is combined with Saquinavir.Approved, Investigational
SecobarbitalThe therapeutic efficacy of Gestodene 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 Gestodene.Approved, Investigational, Vet Approved
St. John's WortThe therapeutic efficacy of Gestodene can be decreased when used in combination with St. John's Wort.Nutraceutical
SugammadexThe serum concentration of Gestodene can be decreased when it is combined with Sugammadex.Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Gestodene.Approved, Investigational
TelaprevirThe serum concentration of Gestodene can be decreased when it is combined with Telaprevir.Approved
ThalidomideGestodene may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Thiopental.Approved, Vet Approved
TipranavirThe serum concentration of Gestodene can be increased when it is combined with Tipranavir.Approved, Investigational
TopiramateThe serum concentration of Gestodene can be decreased when it is combined with Topiramate.Approved
Tranexamic AcidGestodene may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
UlipristalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Ulipristal.Approved
VoriconazoleThe serum concentration of Gestodene can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinGestodene may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Gestodene.Approved, Investigational, Withdrawn
Ym150The therapeutic efficacy of Ym150 can be decreased when used in combination with Gestodene.Investigational
Food InteractionsNot Available
References
Synthesis Reference

Rino Prendin, Silvio Pirovano, “Process for the preparation of gestodene.” U.S. Patent US5719300, issued March, 1994.

US5719300
General ReferencesNot Available
External Links
ATC CodesG03AA10G03AB06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9424
Caco-2 permeable+0.7998
P-glycoprotein substrateSubstrate0.6143
P-glycoprotein inhibitor INon-inhibitor0.5333
P-glycoprotein inhibitor IINon-inhibitor0.7978
Renal organic cation transporterNon-inhibitor0.7228
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9183
CYP450 3A4 substrateSubstrate0.725
CYP450 1A2 substrateNon-inhibitor0.8346
CYP450 2C9 inhibitorNon-inhibitor0.8818
CYP450 2D6 inhibitorNon-inhibitor0.9207
CYP450 2C19 inhibitorInhibitor0.8764
CYP450 3A4 inhibitorNon-inhibitor0.734
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5564
Ames testNon AMES toxic0.9167
CarcinogenicityNon-carcinogens0.9291
BiodegradationNot ready biodegradable0.9835
Rat acute toxicity1.7480 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7927
hERG inhibition (predictor II)Non-inhibitor0.7717
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point197.9 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00581 mg/mLALOGPS
logP3.15ALOGPS
logP3.46ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.08ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.99 m3·mol-1ChemAxon
Polarizability35.94 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
  • Ynone
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Comments
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Drug created on August 18, 2010 14:51 / Updated on August 17, 2016 12:24