Quinestrol

Common Name

Quinestrol Description

Quinestrol is only found in individuals that have used or taken this drug. It is a 3-cyclopentyl ether of ethinyl estradiol.Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regliate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globliin (SHBG), thyroid-binding globliin (TBG), and other serum proteins and suppress follicle-stimliating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globliin (SHBG), thyroid-binding globliin (TBG), and other serum proteins and suppress follicle-stimliating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). Structure

Synonyms

Value Source 17-alpha-Ethinylestradiol 3-cyclopentyl etherChEBI 17alpha-Ethynylestradiol 3-cyclopentyl etherChEBI EstonChEBI Estradiol-17-beta 3-cyclopentyl etherChEBI EstrovisChEBI Estrovis 4000ChEBI EstrovisterChEBI PlestrovisChEBI QuileaChEBI QuinestrolumChEBI 17-a-Ethinylestradiol 3-cyclopentyl etherGenerator 17-α-ethinylestradiol 3-cyclopentyl etherGenerator 17a-Ethynylestradiol 3-cyclopentyl etherGenerator 17α-ethynylestradiol 3-cyclopentyl etherGenerator Estradiol-17-b 3-cyclopentyl etherGenerator Estradiol-17-β 3-cyclopentyl etherGenerator QuinestroloHMDB Ethinyl estradiol 3 cyclopentyl etherMeSH Parke davis brand OF quinestrolMeSH Ethinyl estradiol 3-cyclopentyl etherMeSH

Chemical Formlia

C₂₅H₃₂O₂ Average Molecliar Weight

364.5204 Monoisotopic Molecliar Weight

364.240230268 IUPAC Name

(1S,10R,11S,14R,15S)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol Traditional Name

quinestrol CAS Registry Number

152-43-2 SMILES

InChI Identifier

InChI Key

PWZUUYSISTUNDW-VAFBSOEGSA-N Chemical 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 moleclies Class

Steroids and steroid derivatives Sub Class

Estrane steroids Direct Parent

Estrane steroids Alternative Parents

17-hydroxysteroids

Phenanthrenes and derivatives

Tetralins

Alkyl aryl ethers

Ynones

Tertiary alcohols

Cyclic alcohols and derivatives

Acetylides

Hydrocarbon derivatives

Substituents

Estrane-skeleton

Hydroxysteroid

17-hydroxysteroid

Phenanthrene

Tetralin

Alkyl aryl ether

Benzenoid

Ynone

Tertiary alcohol

Cyclic alcohol

Ether

Acetylide

Organooxygen compound

Alcohol

Hydrocarbon derivative

Organic oxygen compound

Aromatic homopolycyclic compound

Molecliar Framework

Aromatic homopolycyclic compounds External Descriptors

terminal acetylenic compound (CHEBI:8716 )

17-hydroxy steroid (CHEBI:8716 )

C18 steroids (estrogens) and derivatives (C07619 )

C18 steroids (estrogens) and derivatives (LMST02010037 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Cell signaling

Estrogens

Fuel and energy storage

Fuel or energy source

Hormone Replacement Agents

Membrane integrity/stability

Application

Nutrients

Pharmaceutical

Stabilizers

Surfactants and Emlisifiers

Cellliar locations

Cytoplasm

Extracellliar

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point107.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.57e-03 g/LNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.0016 mg/mLALOGPS logP5.19ALOGPS logP5.4ChemAxon logS-5.4ALOGPS pKa (Strongest Acidic)17.59ChemAxon pKa (Strongest Basic)-1.7ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area29.46 ŲChemAxon Rotatable Bond Count2ChemAxon Refractivity108.27 m³·mol^-1ChemAxon Polarizability44.02 ųChemAxon Number of Rings5ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-0a59-2920000000-99119dee5db3aab05906View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04575

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04575

21059682

details

Abnormal Concentrations

Not Available Predicted Concentrations

Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB04575 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

8694 KEGG Compound ID

C07619 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Quinestrol NuGOwiki Link

HMDB15579 Metagene Link

HMDB15579 METLIN ID

Not Available PubChem Compound

9046 PDB ID

Not Available ChEBI ID

8716

Product: Anagrelide (hydrochloride)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

Enzymes

General function:

Involved in sequence-specific DNA binding transcription factor activity

Specific function:

Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1

Gene Name:

ESR1

Uniprot ID:

P03372

Molecular weight:

66215.4

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
4. Shyu C, Cavileer TD, Nagler JJ, Ytreberg FM: Computational estimation of rainbow trout estrogen receptor binding affinities for environmental estrogens. Toxicol Appl Pharmacol. 2011 Feb 1;250(3):322-6. doi: 10.1016/j.taap.2010.11.005. Epub 2010 Nov 12. [PubMed:21075131 ]

PMID: 20232824

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