Lynestrenol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Lynestrenol
DrugBank Accession Number
DB12474
Background

Lynestrenol has been used in trials studying the basic science of Transsexualism and Gender Dysphoria.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 284.443
Monoisotopic: 284.214015522
Chemical Formula
C20H28O
Synonyms
  • Lynestrenol
External IDs
  • NSC-37725

Pharmacology

Indication

Not Available

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our 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 Lynestrenol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Lynestrenol can be increased when combined with Abatacept.
AbciximabThe risk or severity of adverse effects can be increased when Lynestrenol is combined with Abciximab.
AbirateroneThe metabolism of Lynestrenol can be decreased when combined with Abiraterone.
AcenocoumarolThe risk or severity of adverse effects can be increased when Lynestrenol is combined with Acenocoumarol.
AcetaminophenThe metabolism of Lynestrenol can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Lynestrenol can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Lynestrenol can be decreased when used in combination with Acetohexamide.
Acetyl sulfisoxazoleThe metabolism of Lynestrenol can be decreased when combined with Acetyl sulfisoxazole.
Acetylsalicylic acidThe metabolism of Lynestrenol can be decreased when combined with Acetylsalicylic acid.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
Not Available

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more

Categories

ATC Codes
G03AB02 — Lynestrenol and ethinylestradiolG03AA03 — Lynestrenol and ethinylestradiolG03FA07 — Lynestrenol and estrogenG03DC03 — LynestrenolG03FB02 — Lynestrenol and estrogenG03AC02 — Lynestrenol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrane steroids
Alternative Parents
17-hydroxysteroids / Delta-4-steroids / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Delta-4-steroid / Estrane-skeleton / Hydrocarbon derivative / Hydroxysteroid / Organic oxygen compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid (CHEBI:31790) / C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C13037) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030127)
Affected organisms
Not Available

Chemical Identifiers

UNII
N2Z8ALG4U5
CAS number
52-76-6
InChI Key
YNVGQYHLRCDXFQ-XGXHKTLJSA-N
InChI
InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,6,15-18,21H,4-5,7-13H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
IUPAC Name
(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@H]34)[C@@H]1CC[C@@]2(O)C#C

References

General References
  1. FDA Thailand Product Information: Dailyton (lynestrenol) oral tablets [Link]
  2. TITCK Product Information: Orgametril (lynestrenol) oral tablets [Link]
KEGG Compound
C13037
PubChem Compound
5857
PubChem Substance
347828712
ChemSpider
5648
RxNav
6529
ChEBI
31790
ChEMBL
CHEMBL2107431
ZINC
ZINC000003875355
Wikipedia
Lynestrenol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceTranssexualism1
4RecruitingBasic ScienceGender Dysphoria1
1CompletedTreatmentInfertility1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral0.5 MG
Tablet, delayed releaseOral
TabletOral
TabletOral5 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00366 mg/mLALOGPS
logP4ALOGPS
logP4.04ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.81 m3·mol-1ChemAxon
Polarizability34.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Enzymes

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. Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]

Drug created on October 20, 2016 22:31 / Updated on February 21, 2021 18:53