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Identification
NameQuinestrol
Accession NumberDB04575
TypeSmall Molecule
GroupsApproved
DescriptionThe 3-cyclopentyl ether of ethinyl estradiol.
Structure
Thumb
Synonyms
17-alpha-Ethinylestradiol 3-cyclopentyl ether
17alpha-Ethynylestradiol 3-cyclopentyl ether
Eston
Estradiol-17-beta 3-cyclopentyl ether
Estrovis
Estrovis 4000
Estrovister
ethinyl estradiol 3-cyclopentyl ether
Plestrovis
Quilea
Quinestrol
Quinestrolo
Quinestrolum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EstrovisNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIJR0N7XD5GZ
CAS number152-43-2
WeightAverage: 364.5204
Monoisotopic: 364.240230268
Chemical FormulaC25H32O2
InChI KeyInChIKey=PWZUUYSISTUNDW-VAFBSOEGSA-N
InChI
InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1
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
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC1CCCC1)C=C3
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Estrane-skeleton
  • Phenanthrene
  • Tetralin
  • Alkyl aryl ether
  • Benzenoid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed in hormone replacement therapy, treating symptoms of menopause such as hot flashes. Also used to treat breast and prostate cancer.
PharmacodynamicsQuinestrol is the 3-cyclopentyl ether of ethinyl estradiol (the active metabolite). After gastrointestinal absorption, it is stored in adipose tissue where it is slowly released and metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol.
Mechanism of actionEstrogens 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 regulate 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 globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating 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 globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating 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).
Related Articles
AbsorptionAbsorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is metabolized in the liver. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.

SubstrateEnzymesProduct
Quinestrol
Not Available
Ethinyl estradiolDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.9483
Caco-2 permeable+0.8214
P-glycoprotein substrateSubstrate0.6542
P-glycoprotein inhibitor INon-inhibitor0.585
P-glycoprotein inhibitor IINon-inhibitor0.8718
Renal organic cation transporterNon-inhibitor0.8168
CYP450 2C9 substrateNon-substrate0.7004
CYP450 2D6 substrateNon-substrate0.9177
CYP450 3A4 substrateSubstrate0.7205
CYP450 1A2 substrateInhibitor0.8321
CYP450 2C9 inhibitorNon-inhibitor0.8873
CYP450 2D6 inhibitorNon-inhibitor0.9494
CYP450 2C19 inhibitorInhibitor0.7307
CYP450 3A4 inhibitorNon-inhibitor0.5178
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.73
Ames testNon AMES toxic0.9105
CarcinogenicityNon-carcinogens0.8635
BiodegradationNot ready biodegradable0.9812
Rat acute toxicity1.9408 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8631
hERG inhibition (predictor II)Inhibitor0.5854
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point107.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00157 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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity108.27 m3·mol-1ChemAxon
Polarizability44.02 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
4-AndrostenedioneThe serum concentration of 4-Androstenedione can be increased when it is combined with Quinestrol.
AbciximabQuinestrol may decrease the anticoagulant activities of Abciximab.
AcenocoumarolQuinestrol may decrease the anticoagulant activities of Acenocoumarol.
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Quinestrol.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Quinestrol.
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Quinestrol.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Quinestrol.
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Quinestrol.
AncrodQuinestrol may decrease the anticoagulant activities of Ancrod.
Anthrax immune globulin humanQuinestrol may increase the thrombogenic activities of Anthrax immune globulin human.
Antithrombin III humanQuinestrol may decrease the anticoagulant activities of Antithrombin III human.
ApixabanQuinestrol may decrease the anticoagulant activities of Apixaban.
ArdeparinQuinestrol may decrease the anticoagulant activities of Ardeparin.
ArgatrobanQuinestrol may decrease the anticoagulant activities of Argatroban.
BecaplerminQuinestrol may decrease the anticoagulant activities of Becaplermin.
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Quinestrol.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Quinestrol.
BivalirudinQuinestrol may decrease the anticoagulant activities of Bivalirudin.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Quinestrol.
C1 Esterase Inhibitor (Human)Quinestrol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
C1 Esterase Inhibitor (Recombinant)Quinestrol may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).
CertoparinQuinestrol may decrease the anticoagulant activities of Certoparin.
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Quinestrol.
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Quinestrol.
Citric AcidQuinestrol may decrease the anticoagulant activities of Citric Acid.
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Quinestrol.
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Quinestrol.
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Quinestrol.
Dabigatran etexilateQuinestrol may decrease the anticoagulant activities of Dabigatran etexilate.
DalteparinQuinestrol may decrease the anticoagulant activities of Dalteparin.
DanaparoidQuinestrol may decrease the anticoagulant activities of Danaparoid.
DehydroepiandrosteroneThe risk or severity of adverse effects can be increased when Dehydroepiandrosterone is combined with Quinestrol.
DehydroepiandrosteroneThe serum concentration of Dehydroepiandrosterone can be increased when it is combined with Quinestrol.
dehydroepiandrosterone sulfateThe serum concentration of dehydroepiandrosterone sulfate can be increased when it is combined with Quinestrol.
DesirudinQuinestrol may decrease the anticoagulant activities of Desirudin.
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Quinestrol.
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Quinestrol.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Quinestrol.
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Quinestrol.
DextranQuinestrol may decrease the anticoagulant activities of Dextran.
Dextran 40Quinestrol may decrease the anticoagulant activities of Dextran 40.
Dextran 70Quinestrol may decrease the anticoagulant activities of Dextran 70.
Dextran 75Quinestrol may decrease the anticoagulant activities of Dextran 75.
DicoumarolQuinestrol may decrease the anticoagulant activities of Dicoumarol.
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Quinestrol.
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Quinestrol.
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Quinestrol.
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Quinestrol.
Edetic AcidQuinestrol may decrease the anticoagulant activities of Edetic Acid.
EdoxabanQuinestrol may decrease the anticoagulant activities of Edoxaban.
EnoxaparinQuinestrol may decrease the anticoagulant activities of Enoxaparin.
EquileninThe serum concentration of Equilenin can be increased when it is combined with Quinestrol.
EquilinThe serum concentration of Equilin can be increased when it is combined with Quinestrol.
EstroneThe serum concentration of Estrone can be increased when it is combined with Quinestrol.
Ethyl biscoumacetateQuinestrol may decrease the anticoagulant activities of Ethyl biscoumacetate.
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Quinestrol.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Quinestrol.
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Quinestrol.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Quinestrol.
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Quinestrol.
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Quinestrol.
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Quinestrol.
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Quinestrol.
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Quinestrol.
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Quinestrol.
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Quinestrol.
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Quinestrol.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Quinestrol.
Fondaparinux sodiumQuinestrol may decrease the anticoagulant activities of Fondaparinux sodium.
HeparinQuinestrol may decrease the anticoagulant activities of Heparin.
HirulogQuinestrol may decrease the anticoagulant activities of Hirulog.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Quinestrol.
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Quinestrol.
LenalidomideQuinestrol may increase the thrombogenic activities of Lenalidomide.
LepirudinQuinestrol may decrease the anticoagulant activities of Lepirudin.
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Quinestrol.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Quinestrol.
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Quinestrol.
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Quinestrol.
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Quinestrol.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Quinestrol.
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Quinestrol.
NadroparinQuinestrol may decrease the anticoagulant activities of Nadroparin.
OspemifeneThe risk or severity of adverse effects can be increased when Quinestrol is combined with Ospemifene.
OtamixabanQuinestrol may decrease the anticoagulant activities of Otamixaban.
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Quinestrol.
Pentosan PolysulfateQuinestrol may decrease the anticoagulant activities of Pentosan Polysulfate.
PhenindioneQuinestrol may decrease the anticoagulant activities of Phenindione.
PhenprocoumonQuinestrol may decrease the anticoagulant activities of Phenprocoumon.
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Quinestrol.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Quinestrol.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Quinestrol.
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Quinestrol.
Protein CQuinestrol may decrease the anticoagulant activities of Protein C.
ProtocatechualdehydeQuinestrol may decrease the anticoagulant activities of Protocatechualdehyde.
ReviparinQuinestrol may decrease the anticoagulant activities of Reviparin.
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Quinestrol.
RivaroxabanQuinestrol may decrease the anticoagulant activities of Rivaroxaban.
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Quinestrol.
Somatropin recombinantThe therapeutic efficacy of Somatropin recombinant can be decreased when used in combination with Quinestrol.
SulodexideQuinestrol may decrease the anticoagulant activities of Sulodexide.
ThalidomideQuinestrol may increase the thrombogenic activities of Thalidomide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Quinestrol.
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with Quinestrol.
TipranavirQuinestrol may increase the dermatologic adverse activities of Tipranavir.
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Quinestrol.
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Quinestrol.
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Quinestrol.
Vitamin CThe serum concentration of Quinestrol can be increased when it is combined with Vitamin C.
WarfarinQuinestrol may decrease the anticoagulant activities of Warfarin.
XimelagatranQuinestrol may decrease the anticoagulant activities of Ximelagatran.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonistmodulator
General Function:
Zinc ion binding
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. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
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 ]
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Drug created on September 07, 2007 15:29 / Updated on August 17, 2016 12:24