Lynestrenol

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

Identification

Summary

Lynestrenol is a progestin used for contraception and in the treatment of menstrual disorders.

Generic Name
Lynestrenol
DrugBank Accession Number
DB12474
Background

Lynestrenol is a progestin and prodrug of norethisterone.

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

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofEndometrial carcinoma••••••••••••••••••
Prevention ofEndometrial hyperplasia••••••••••••••••••
Treatment ofEndometriosis••••••••••••••••••
Treatment ofHypermenorrhea••••••••••••••••••
Treatment ofMenstrual cramps••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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

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.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Lynestrenol.
AcenocoumarolThe risk or severity of adverse effects can be increased when Lynestrenol is combined with Acenocoumarol.
Food Interactions
Not Available

Products

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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
4Unknown StatusBasic ScienceGender Dysphoria1
1CompletedTreatmentInfertility1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral0.5 MG
Tablet, delayed releaseOral0.5 mg
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/MSsplash10-000i-0090000000-c0c43efa7aa7d77f6f64
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-54ebf6593cac47f5bab3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-1690000000-493b0de92cce9a2ea635
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-af5f6b5503620dd5658d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-fdfa3a374897fa53f553
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-7900000000-9ace315e35dda052218a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.3926
predicted
DeepCCS 1.0 (2019)
[M+H]+183.75058
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.69296
predicted
DeepCCS 1.0 (2019)

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 at October 20, 2016 22:31 / Updated at May 27, 2021 02:58