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
Type
Small Molecule
Groups
Approved, Investigational
Description

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

Structure
Thumb
Synonyms
Not Available
External IDs
NSC-37725
Categories
UNII
N2Z8ALG4U5
CAS number
52-76-6
Weight
Average: 284.443
Monoisotopic: 284.214015522
Chemical Formula
C20H28O
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbciximabLynestrenol may decrease the anticoagulant activities of Abciximab.
AcenocoumarolLynestrenol may decrease the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidLynestrenol may decrease the anticoagulant activities of Acetylsalicylic acid.
AcitretinThe therapeutic efficacy of Lynestrenol can be decreased when used in combination with Acitretin.
AdapaleneThe therapeutic efficacy of Lynestrenol can be decreased when used in combination with Adapalene.
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Lynestrenol.
AlfuzosinThe metabolism of Lynestrenol can be decreased when combined with Alfuzosin.
AlitretinoinThe therapeutic efficacy of Lynestrenol can be decreased when used in combination with Alitretinoin.
AlteplaseLynestrenol may decrease the anticoagulant activities of Alteplase.
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Lynestrenol.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C13037
PubChem Compound
5857
PubChem Substance
347828712
ChemSpider
5648
ChEBI
31790
ChEMBL
CHEMBL2107431
Wikipedia
Lynestrenol
ATC Codes
G03AA03 — Lynestrenol and ethinylestradiolG03DC03 — LynestrenolG03AC02 — LynestrenolG03FA07 — Lynestrenol and estrogenG03FB02 — Lynestrenol and estrogenG03AB02 — Lynestrenol and ethinylestradiol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceTranssexualism1
4RecruitingBasic ScienceGender Dysphoria1

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

Taxonomy

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 / Hydroxysteroid / Estrane-skeleton / Delta-4-steroid / Ynone / Tertiary alcohol / Cyclic alcohol / Acetylide / Organic oxygen compound / Hydrocarbon derivative
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)

Enzymes

Kind
Protein
Organism
Human
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
Human
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
Human
Pharmacological action
No
Actions
Substrate
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 September 13, 2018 16:02