Gestodene
Identification
- Name
- Gestodene
- Accession Number
- DB06730
- 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.
- 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
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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 Unlock Additional DataAbametapir The serum concentration of Gestodene can be increased when it is combined with Abametapir. Abciximab Gestodene may decrease the anticoagulant activities of Abciximab. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Gestodene. 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. Acetylsalicylic acid Gestodene may decrease the anticoagulant activities of Acetylsalicylic acid. 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. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Mixture 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 
- 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
- Contraceptives, Oral
- 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 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
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[[email protected]]12CC[[email protected]]3[[email protected]@H](CCC4=CC(=O)CC[[email protected]]34)[[email protected]@H]1C=C[[email protected]@]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 Other Ovulation Inhibition 1 4 Completed Treatment Contraception / Menopause / Quality of Life 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 2 Unknown Status Treatment Periodontitis 1 1 Completed Treatment Contraception 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral 20 mcg Tablet, film coated Oral 15 mcg Tablet, coated Oral 0.03 mg Tablet, coated Oral 30 mcg Tablet, sugar coated Oral 30 mg Tablet, film coated Oral 0.06 mg Tablet, coated Oral 20 µg Tablet, sugar coated Oral 20 mcg Tablet, sugar coated Oral 75 mcg Tablet, coated Oral 0.015 mg Tablet, coated Oral 15 mcg Tablet, film coated Oral 60 mcg Tablet, coated Oral 75 mcg Tablet Oral 30 mcg Tablet Oral Tablet, coated Oral 0.075 mg Tablet, coated Oral 0.02 mg Tablet, sugar coated Oral 50 mcg Tablet, sugar coated Oral 0.075 mg - 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 35.94 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
- 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. [PubMed:15697108]
- 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
- 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]
- 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
- 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]
- 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. [PubMed:12899669]
Drug created on August 18, 2010 14:51 / Updated on June 12, 2020 10:52
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