Identification

Name
Gestodene
Accession Number
DB06730
Type
Small Molecule
Groups
Investigational
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
  • Gestodene
  • Gestodeno
  • Gestodenum
External IDs
SH B 331 / SH-B-331
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MyvlarGestodene (0.075 mg/1) + Ethinylestradiol (0.03 mg/1)TabletOralOASIS TRADING2018-11-22Not applicableUs
Categories
UNII
1664P6E6MI
CAS number
60282-87-3
Weight
Average: 310.4299
Monoisotopic: 310.193280076
Chemical Formula
C21H26O2
InChI Key
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[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1C=C[C@@]2(O)C#C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AProgesterone receptor
binder
activator
Human
Absorption

in vitro 99% using 3H=R5020 / in vivo similar to progesterone

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

16 to 18 hrs.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinGestodene may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinGestodene may decrease the anticoagulant activities of (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Gestodene.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Gestodene.
5-androstenedioneThe metabolism of Gestodene can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Gestodene can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Gestodene.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Gestodene.
AbataceptThe metabolism of Gestodene can be increased when combined with Abatacept.
AbciximabGestodene may decrease the anticoagulant activities of Abciximab.
Food Interactions
Not Available

References

Synthesis Reference

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

US5719300
General References
Not Available
External Links
Human Metabolome Database
HMDB0015668
PubChem Compound
3033968
PubChem Substance
99443276
ChemSpider
2298532
ChEBI
135323
ChEMBL
CHEMBL1213583
PharmGKB
PA165958397
Wikipedia
Gestodene
ATC Codes
G03AA10 — Gestodene and ethinylestradiolG03AB06 — Gestodene and ethinylestradiol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentContraception1
2CompletedPreventionContraception4
2CompletedTreatmentContraception / Ovulation Inhibition1
2TerminatedTreatmentContraception / Ovulation Inhibition1
3CompletedPreventionContraception4
4CompletedTreatmentContraception / Menopause / Quality of Life1
4TerminatedScreeningContraception / Hypercoagulability1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)197.9 °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 RuleNoChemAxon
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)

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-oxosteroids / 17-hydroxysteroids / Cyclohexenones / Ynones / Tertiary alcohols / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-oxosteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / Cyclohexenone / Ynone / Tertiary alcohol / Ketone / Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Binder
Activator
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. Benagiano G, Primiero FM, Farris M: Clinical profile of contraceptive progestins. Eur J Contracept Reprod Health Care. 2004 Sep;9(3):182-93. [PubMed:15697108]
  2. Bardal S, Waechter J, Martin D. (2011). Applied Pharmacology. Elsevier Health Sciences. [ISBN:978-1-4377-0310-8]

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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
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. Palovaara S, Kivisto KT, Tapanainen P, Manninen P, Neuvonen PJ, Laine K: Effect of an oral contraceptive preparation containing ethinylestradiol and gestodene on CYP3A4 activity as measured by midazolam 1'-hydroxylation. Br J Clin Pharmacol. 2000 Oct;50(4):333-7. [PubMed:11012556]

Drug created on August 18, 2010 14:51 / Updated on December 16, 2018 06:53