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
Structure for Gestodene (DB06730)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AProgesterone receptor binderactivatorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Gestodene can be increased when it is combined with Abametapir. Abciximab The risk or severity of adverse effects can be increased when Gestodene is combined with Abciximab. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Gestodene. Acenocoumarol The risk or severity of adverse effects can be increased when Gestodene is combined with Acenocoumarol. Acetaminophen The metabolism of Gestodene can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Gestodene can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Gestodene. Acitretin The therapeutic efficacy of Gestodene can be decreased when used in combination with Acitretin. Albendazole The metabolism of Albendazole can be decreased when combined with Gestodene. Alfentanil The metabolism of Alfentanil can be decreased when combined with Gestodene. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CICLOMEX-20 Gestodene (75 mcg) + Ethinylestradiol (20 mcg) Tablet, coated Oral บริษัท เอ็กเซลทิส (ประเทศไทย) จำกัด 2008-11-11 Not applicable Thailand 
FEMIANE® Gestodene (75 mcg) + Ethinylestradiol (20 mcg) Tablet, coated Oral BAYER S.A 2006-11-10 2019-01-31 Colombia 
GESTODENO + ETINILESTRADIOL75+20 MCG Gestodene (75 cg) + Ethinylestradiol (20 cg) Tablet, coated Oral EUROFARMA LABORATORIOS S.A 2015-05-21 2021-04-01 Colombia GINERA DRAJE, 21 ADET Gestodene (0.075 mg) + Ethinylestradiol (0.03 mg) Tablet, coated Oral BAYER TÜRK KİMYA SAN. LTD. ŞTİ. 2020-08-14 Not applicable Turkey 
MELIANE TABLETS Gestodene (0.075 mg) + Ethinylestradiol (0.02 mg) Tablet, sugar coated Oral BAYER (SOUTH EAST ASIA) PTE LTD 1998-07-02 Not applicable Singapore Myvlar Gestodene (0.075 mg/1) + Ethinylestradiol (0.03 mg/1) Tablet Oral OASIS TRADING 2018-11-22 Not applicable US 
REGINON 0,02 MG /0,075 MG 21 DRAJE Gestodene (0.075 mg) + Ethinylestradiol (0.02 mg) Tablet, coated Oral KOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş. 2020-08-14 Not applicable Turkey REGINON 0,02 MG /0,075 MG 63 DRAJE Gestodene (0.075 mg) + Ethinylestradiol (0.02 mg) Tablet, coated Oral KOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş. 2020-08-14 Not applicable Turkey REGINON 0,030MG/0,075MG 21 DRAJE Gestodene (0.075 mg) + Ethinylestradiol (0.03 mg) Tablet, coated Oral KOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş. 2020-08-14 Not applicable Turkey REGİNON 0.02 MG/0.075 MG DRAJE , 1050 ADET Gestodene (0.075 mg) + Ethinylestradiol (0.02 mg) Tablet, coated Oral KOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş. 2020-08-14 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Myvlar Gestodene (0.075 mg/1) + Ethinylestradiol (0.03 mg/1) Tablet Oral OASIS TRADING 2018-11-22 Not applicable US
Categories
- ATC Codes
- G03AA10 — Gestodene and ethinylestradiol
- G03AA — Progestogens and estrogens, fixed combinations
- G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Adrenal Cortex Hormones
- Combination Contraceptives (with Estrogen and derivatives)
- Contraceptive Agents, Female
- Contraceptive Agents, Hormonal
- Contraceptives, Oral
- Contraceptives, Oral, Hormonal
- Contraceptives, Oral, Synthetic
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormonal Contraceptives for Systemic Use
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Norpregnanes
- Norsteroids
- Progestin Contraceptives
- Progestins
- Progestogens and Estrogens, Sequential Preparations
- Reproductive Control Agents
- Sex Hormones and Modulators of the Genital System
- Steroids
- 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
- (1R,3aS,3bR,9aR,9bS,11aS)-11a-ethyl-1-ethynyl-1-hydroxy-1H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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
- External Links
- Human Metabolome Database
- HMDB0015668
- PubChem Compound
- 3033968
- PubChem Substance
- 99443276
- ChemSpider
- 2298532
- 25734
- ChEBI
- 135323
- ChEMBL
- CHEMBL1213583
- ZINC
- ZINC000238809420
- PharmGKB
- PA165958397
- Wikipedia
- Gestodene
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Contraception / Menopause / Quality of Life (QOL) 1 4 Completed Treatment Endometriosis 1 4 Terminated Screening Contraception / Hypercoagulability 1 3 Completed Prevention Contraception 4 2 Completed Prevention Contraception 4 2 Completed Treatment Contraception / Ovulation Inhibition 1 2 Terminated Treatment Contraception / Ovulation Inhibition 1 1 Completed Treatment Contraception 1 1, 2 Recruiting Treatment Sub Fertility, Female 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 15 MCG Tablet, delayed release Oral Tablet, coated Oral 0.02 MG Tablet, coated Oral Tablet, film coated Oral Tablet, sugar coated Oral 0.02 mg Tablet Oral Kit; tablet, coated Oral Tablet, sugar coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 197.9 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.00581 mg/mL ALOGPS logP 3.15 ALOGPS logP 3.46 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 17.08 ChemAxon pKa (Strongest Basic) -1.9 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 92.99 m3·mol-1 ChemAxon Polarizability 35.96 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9424 Caco-2 permeable + 0.7998 P-glycoprotein substrate Substrate 0.6143 P-glycoprotein inhibitor I Non-inhibitor 0.5333 P-glycoprotein inhibitor II Non-inhibitor 0.7978 Renal organic cation transporter Non-inhibitor 0.7228 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Non-substrate 0.9183 CYP450 3A4 substrate Substrate 0.725 CYP450 1A2 substrate Non-inhibitor 0.8346 CYP450 2C9 inhibitor Non-inhibitor 0.8818 CYP450 2D6 inhibitor Non-inhibitor 0.9207 CYP450 2C19 inhibitor Inhibitor 0.8764 CYP450 3A4 inhibitor Non-inhibitor 0.734 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5564 Ames test Non AMES toxic 0.9167 Carcinogenicity Non-carcinogens 0.9291 Biodegradation Not ready biodegradable 0.9835 Rat acute toxicity 1.7480 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7927 hERG inhibition (predictor II) Non-inhibitor 0.7717
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- BinderActivator
- 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
- Benagiano G, Primiero FM, Farris M: Clinical profile of contraceptive progestins. Eur J Contracept Reprod Health Care. 2004 Sep;9(3):182-93. [Article]
- 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
- No
- Actions
- SubstrateInhibitor
- 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
- 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]
- Zhou S, Yung Chan S, Cher Goh B, Chan E, Duan W, Huang M, McLeod HL: Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin Pharmacokinet. 2005;44(3):279-304. doi: 10.2165/00003088-200544030-00005. [Article]
- 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
- 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]
- 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
- 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
- Flockhart Table of Drug Interactions [Link]
Drug created at August 18, 2010 20:51 / Updated at September 28, 2021 21:54