Gestodene

Identification

Generic Name
Gestodene
DrugBank Accession Number
DB06730
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 310.4299
Monoisotopic: 310.193280076
Chemical Formula
C21H26O2
Synonyms
  • Gestodene
  • Gestodeno
  • Gestodenum
External IDs
  • SH B 331
  • SH-B-331

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AProgesterone receptor
binder
activator
Humans
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

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Gestodene can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of adverse effects can be increased when Gestodene is combined with Abciximab.
AbirateroneThe metabolism of Gestodene can be decreased when combined with Abiraterone.
AcenocoumarolThe risk or severity of adverse effects can be increased when Gestodene is combined with Acenocoumarol.
AcetaminophenThe metabolism of Gestodene can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Gestodene can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Gestodene.
AcitretinThe therapeutic efficacy of Gestodene can be decreased when used in combination with Acitretin.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Gestodene.
AlfentanilThe metabolism of Alfentanil can be decreased when combined with Gestodene.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
Not Available

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CICLOMEX-20Gestodene (75 mcg) + Ethinylestradiol (20 mcg)Tablet, coatedOralบริษัท เอ็กเซลทิส (ประเทศไทย) จำกัด2008-11-11Not applicableThailand flag
FEMIANE®Gestodene (75 mcg) + Ethinylestradiol (20 mcg)Tablet, coatedOralBAYER S.A2006-11-102019-01-31Colombia flag
GINERA DRAJE, 21 ADETGestodene (0.075 mg) + Ethinylestradiol (0.03 mg)Tablet, coatedOralBAYER TÜRK KİMYA SAN. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
MyvlarGestodene (0.075 mg/1) + Ethinylestradiol (0.03 mg/1)TabletOralOASIS TRADING2018-11-22Not applicableUS flag
REGINON 0,02 MG /0,075 MG 21 DRAJEGestodene (0.075 mg) + Ethinylestradiol (0.02 mg)Tablet, coatedOralKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
REGINON 0,02 MG /0,075 MG 63 DRAJEGestodene (0.075 mg) + Ethinylestradiol (0.02 mg)Tablet, coatedOralKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
REGINON 0,030MG/0,075MG 21 DRAJEGestodene (0.075 mg) + Ethinylestradiol (0.03 mg)Tablet, coatedOralKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
REGİNON 0.02 MG/0.075 MG DRAJE , 1050 ADETGestodene (0.075 mg) + Ethinylestradiol (0.02 mg)Tablet, coatedOralKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
REGİNON0.02 MG/0.075 MG DRAJE , 2100 ADETGestodene (0.075 mg) + Ethinylestradiol (0.02 mg)Tablet, coatedOralKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
คลาเรนซ์Gestodene (75 MCG) + Ethinylestradiol (20 MCG)Tablet, coatedOralบริษัท ไทยนครพัฒนา จำกัด2019-10-09Not applicableThailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
MyvlarGestodene (0.075 mg/1) + Ethinylestradiol (0.03 mg/1)TabletOralOASIS TRADING2018-11-22Not applicableUS flag

Categories

ATC Codes
G03AA10 — Gestodene and ethinylestradiolG03AB06 — Gestodene and ethinylestradiol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
17-hydroxysteroid / 3-oxosteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic ketone / Cyclohexenone / Estrogen-skeleton / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
1664P6E6MI
CAS number
60282-87-3
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

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
Human Metabolome Database
HMDB0015668
PubChem Compound
3033968
PubChem Substance
99443276
ChemSpider
2298532
RxNav
25734
ChEBI
135323
ChEMBL
CHEMBL1213583
ZINC
ZINC000238809420
PharmGKB
PA165958397
Wikipedia
Gestodene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentContraception / Menopause / Quality of Life (QOL)1
4CompletedTreatmentEndometriosis1
4TerminatedScreeningContraception / Hypercoagulability1
3CompletedPreventionContraception4
2CompletedPreventionContraception4
2CompletedTreatmentContraception / Ovulation Inhibition1
2TerminatedTreatmentContraception / Ovulation Inhibition1
1CompletedTreatmentContraception1
1, 2RecruitingTreatmentSub Fertility, Female1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral15 MCG
Tablet, delayed releaseOral
Tablet, coatedOral0.02 MG
Tablet, film coatedOral
Tablet, sugar coatedOral
Tablet, coatedOral
Kit; tablet, coatedOral
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

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
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. [Article]
  2. Bardal S, Waechter J, Martin D. (2011). Applied Pharmacology. Elsevier Health Sciences. [ISBN:978-1-4377-0310-8]

Enzymes

Kind
Protein
Organism
Humans
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. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Laine K, Yasar U, Widen J, Tybring G: A screening study on the liability of eight different female sex steroids to inhibit CYP2C9, 2C19 and 3A4 activities in human liver microsomes. Pharmacol Toxicol. 2003 Aug;93(2):77-81. [Article]

Drug created on August 18, 2010 20:51 / Updated on February 21, 2021 18:52