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Identification
NameGestodene
Accession NumberDB06730
TypeSmall Molecule
GroupsApproved
Description

Gestodene 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 KeyInChIKey=SIGSPDASOTUPFS-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
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
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
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
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
Interactions
Drug Interactions
Drug
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Gestodene.
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Gestodene.
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Gestodene.
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Gestodene.
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Gestodene.
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Gestodene.
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Gestodene.
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Gestodene.
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Gestodene.
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Gestodene.
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Gestodene.
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Gestodene.
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Gestodene.
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Gestodene.
TinzaparinThe therapeutic efficacy of Tinzaparin can be decreased when used in combination with Gestodene.
UlipristalThe therapeutic efficacy of Gestodene can be decreased when used in combination with Ulipristal.
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Gestodene.
Food InteractionsNot 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