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Identification
NameHexestrol
Accession NumberDB07931  (DB08959)
TypeSmall Molecule
GroupsWithdrawn
DescriptionA synthetic estrogen that has been used as a hormonal antineoplastic agent.
Structure
Thumb
Synonyms
4,4'-(1,2-diethylethylene)diphenol
Erythrohexestrol
Hexanoestrol
Hexoestrolum
Meso-3,4-di(p-hydroxyphenyl)-n-hexane
Meso-hexestrol
Mesohexestrol
Synoestrolum
External Identifiers
  • NSC-9894
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EstrifarNot Available
EstronalNot Available
HexoestrolTai Yu
SynestrolBiopharm
SynoestrolNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Hexestrol diphosphate sodium
171399-06-7
Thumb
  • InChI Key: DNCWQZVLWAEATB-YHCLLLHXSA-J
  • Monoisotopic Mass: 518.02241872
  • Average Mass: 518.257
DBSALT001081
Categories
UNII10BI795R7D
CAS number84-16-2
WeightAverage: 270.3661
Monoisotopic: 270.161979948
Chemical FormulaC18H22O2
InChI KeyInChIKey=PBBGSZCBWVPOOL-HDICACEKSA-N
InChI
InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+
IUPAC Name
4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
SMILES
[H][C@](CC)(C1=CC=C(O)C=C1)[C@]([H])(CC)C1=CC=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenylpropane
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9959
Blood Brain Barrier+0.7575
Caco-2 permeable+0.8705
P-glycoprotein substrateNon-substrate0.5375
P-glycoprotein inhibitor INon-inhibitor0.8556
P-glycoprotein inhibitor IINon-inhibitor0.8622
Renal organic cation transporterNon-inhibitor0.8652
CYP450 2C9 substrateNon-substrate0.7865
CYP450 2D6 substrateNon-substrate0.8813
CYP450 3A4 substrateNon-substrate0.602
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.7855
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.5469
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8156
Ames testNon AMES toxic0.9648
CarcinogenicityNon-carcinogens0.6254
BiodegradationNot ready biodegradable0.9528
Rat acute toxicity1.9859 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8238
hERG inhibition (predictor II)Non-inhibitor0.5976
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 point185U.S. Patent 2,357,985; U.S. Patent 2,421,401.
Predicted Properties
PropertyValueSource
Water Solubility0.0139 mg/mLALOGPS
logP4.98ALOGPS
logP5.37ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.66 m3·mol-1ChemAxon
Polarizability31.31 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,357,985; U.S. Patent 2,421,401.

General References
  1. Liehr JG, Ballatore AM, Dague BB, Ulubelen AA: Carcinogenicity and metabolic activation of hexestrol. Chem Biol Interact. 1985 Oct;55(1-2):157-76. [PubMed:2998630 ]
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 Hexestrol.
AbciximabHexestrol may decrease the anticoagulant activities of Abciximab.
AcenocoumarolHexestrol may decrease the anticoagulant activities of Acenocoumarol.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Hexestrol.
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Hexestrol.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Hexestrol.
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Hexestrol.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Hexestrol.
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Hexestrol.
AncrodHexestrol may decrease the anticoagulant activities of Ancrod.
Anthrax immune globulin humanHexestrol may increase the thrombogenic activities of Anthrax immune globulin human.
Antithrombin III humanHexestrol may decrease the anticoagulant activities of Antithrombin III human.
ApixabanHexestrol may decrease the anticoagulant activities of Apixaban.
ArdeparinHexestrol may decrease the anticoagulant activities of Ardeparin.
ArgatrobanHexestrol may decrease the anticoagulant activities of Argatroban.
BecaplerminHexestrol may decrease the anticoagulant activities of Becaplermin.
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Hexestrol.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Hexestrol.
BevacizumabBevacizumab may increase the cardiotoxic activities of Hexestrol.
BivalirudinHexestrol may decrease the anticoagulant activities of Bivalirudin.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Hexestrol.
C1 Esterase Inhibitor (Human)Hexestrol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
C1 Esterase Inhibitor (Recombinant)Hexestrol may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Hexestrol.
CertoparinHexestrol may decrease the anticoagulant activities of Certoparin.
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Hexestrol.
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Hexestrol.
Citric AcidHexestrol may decrease the anticoagulant activities of Citric Acid.
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Hexestrol.
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Hexestrol.
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Hexestrol.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Hexestrol.
Dabigatran etexilateHexestrol may decrease the anticoagulant activities of Dabigatran etexilate.
DalteparinHexestrol may decrease the anticoagulant activities of Dalteparin.
DanaparoidHexestrol may decrease the anticoagulant activities of Danaparoid.
DehydroepiandrosteroneThe risk or severity of adverse effects can be increased when Dehydroepiandrosterone is combined with Hexestrol.
DehydroepiandrosteroneThe serum concentration of Dehydroepiandrosterone can be increased when it is combined with Hexestrol.
dehydroepiandrosterone sulfateThe serum concentration of dehydroepiandrosterone sulfate can be increased when it is combined with Hexestrol.
DesirudinHexestrol may decrease the anticoagulant activities of Desirudin.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Hexestrol.
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Hexestrol.
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Hexestrol.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Hexestrol.
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Hexestrol.
DextranHexestrol may decrease the anticoagulant activities of Dextran.
Dextran 40Hexestrol may decrease the anticoagulant activities of Dextran 40.
Dextran 70Hexestrol may decrease the anticoagulant activities of Dextran 70.
Dextran 75Hexestrol may decrease the anticoagulant activities of Dextran 75.
DicoumarolHexestrol may decrease the anticoagulant activities of Dicoumarol.
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Hexestrol.
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Hexestrol.
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Hexestrol.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Hexestrol.
DigoxinDigoxin may decrease the cardiotoxic activities of Hexestrol.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Hexestrol.
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Hexestrol.
Edetic AcidHexestrol may decrease the anticoagulant activities of Edetic Acid.
EdoxabanHexestrol may decrease the anticoagulant activities of Edoxaban.
EnoxaparinHexestrol may decrease the anticoagulant activities of Enoxaparin.
EquileninThe serum concentration of Equilenin can be increased when it is combined with Hexestrol.
EquilinThe serum concentration of Equilin can be increased when it is combined with Hexestrol.
EstroneThe serum concentration of Estrone can be increased when it is combined with Hexestrol.
Ethyl biscoumacetateHexestrol may decrease the anticoagulant activities of Ethyl biscoumacetate.
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Hexestrol.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Hexestrol.
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Hexestrol.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Hexestrol.
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Hexestrol.
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Hexestrol.
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Hexestrol.
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Hexestrol.
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Hexestrol.
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Hexestrol.
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Hexestrol.
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Hexestrol.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Hexestrol.
Fondaparinux sodiumHexestrol may decrease the anticoagulant activities of Fondaparinux sodium.
HeparinHexestrol may decrease the anticoagulant activities of Heparin.
HirulogHexestrol may decrease the anticoagulant activities of Hirulog.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Hexestrol.
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Hexestrol.
LenalidomideHexestrol may increase the thrombogenic activities of Lenalidomide.
LepirudinHexestrol may decrease the anticoagulant activities of Lepirudin.
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Hexestrol.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Hexestrol.
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Hexestrol.
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Hexestrol.
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Hexestrol.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Hexestrol.
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Hexestrol.
NadroparinHexestrol may decrease the anticoagulant activities of Nadroparin.
OspemifeneThe risk or severity of adverse effects can be increased when Hexestrol is combined with Ospemifene.
OtamixabanHexestrol may decrease the anticoagulant activities of Otamixaban.
OuabainOuabain may decrease the cardiotoxic activities of Hexestrol.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Hexestrol.
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Hexestrol.
Pentosan PolysulfateHexestrol may decrease the anticoagulant activities of Pentosan Polysulfate.
PhenindioneHexestrol may decrease the anticoagulant activities of Phenindione.
PhenprocoumonHexestrol may decrease the anticoagulant activities of Phenprocoumon.
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Hexestrol.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Hexestrol.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Hexestrol.
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Hexestrol.
Protein CHexestrol may decrease the anticoagulant activities of Protein C.
ProtocatechualdehydeHexestrol may decrease the anticoagulant activities of Protocatechualdehyde.
ReviparinHexestrol may decrease the anticoagulant activities of Reviparin.
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Hexestrol.
RivaroxabanHexestrol may decrease the anticoagulant activities of Rivaroxaban.
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Hexestrol.
Somatropin recombinantThe therapeutic efficacy of Somatropin recombinant can be decreased when used in combination with Hexestrol.
SulodexideHexestrol may decrease the anticoagulant activities of Sulodexide.
ThalidomideHexestrol may increase the thrombogenic activities of Thalidomide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Hexestrol.
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with Hexestrol.
TipranavirHexestrol may increase the dermatologic adverse activities of Tipranavir.
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Hexestrol.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Hexestrol.
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Hexestrol.
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Hexestrol.
Vitamin CThe serum concentration of Hexestrol can be increased when it is combined with Vitamin C.
WarfarinHexestrol may decrease the anticoagulant activities of Warfarin.
XimelagatranHexestrol may decrease the anticoagulant activities of Ximelagatran.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular Weight:
36788.02 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Comments
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Drug created on September 15, 2010 15:27 / Updated on August 17, 2016 12:24