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Identification
NameHexestrol
Accession NumberDB07931  (DB08959)
TypeSmall Molecule
GroupsWithdrawn
Description

A 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
CategoriesNot Available
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 InteractionsNot Available
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 ]
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Drug created on September 15, 2010 15:27 / Updated on May 07, 2016 20:34