Lynestrenol

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

Identification

Name
Lynestrenol
Accession Number
DB12474
Description

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
Not Available
External IDs
  • NSC-37725

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
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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.
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.
AbciximabLynestrenol may decrease the anticoagulant activities of Abciximab.
AbirateroneThe metabolism of Lynestrenol can be decreased when combined with Abiraterone.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Lynestrenol.
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 acidLynestrenol may decrease the anticoagulant activities of Acetylsalicylic acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

Categories

ATC Codes
G03AB02 — Lynestrenol and ethinylestradiolG03AA03 — Lynestrenol and ethinylestradiolG03DC03 — LynestrenolG03FA07 — Lynestrenol and estrogenG03FB02 — 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)

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
Not Available
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
Not Available
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. [PubMed:18356043]
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. [PubMed:18356043]
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. [PubMed:18356043]

Drug created on October 20, 2016 16:31 / Updated on June 12, 2020 10:53

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