NAV

Hexestrol

Identification

Generic Name
Hexestrol
DrugBank Accession Number
DB07931
Background

A synthetic estrogen that has been used as a hormonal antineoplastic agent.

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 270.3661
Monoisotopic: 270.161979948
Chemical Formula
C18H22O2
Synonyms
  • 4,4'-(1,2-diethylethylene)diphenol
  • Erythrohexestrol
  • Hexanoestrol
  • Hexestrol
  • Hexoestrolum
  • Meso-3,4-di(p-hydroxyphenyl)-n-hexane
  • Meso-hexestrol
  • Mesohexestrol
  • Synoestrolum
External IDs
  • NSC-9894
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAldo-keto reductase family 1 member C1Not AvailableHumans
UEstrogen receptor alphaNot AvailableHumans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
UNuclear receptor subfamily 1 group I member 3Not AvailableHumans
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Integrate drug-drug
interactions in your software
AbciximabHexestrol may decrease the anticoagulant activities of Abciximab.
AceclofenacAceclofenac may increase the thrombogenic activities of Hexestrol.
AcenocoumarolHexestrol may decrease the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Hexestrol.
AdalimumabHexestrol may increase the thrombogenic activities of Adalimumab.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hexestrol diphosphate sodiumVK60X9E36E171399-06-7DNCWQZVLWAEATB-YHCLLLHXSA-J
International/Other Brands
Estrifar / Estronal / Hexoestrol (Tai Yu) / Synestrol (Biopharm) / Synoestrol

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Phenylpropanes / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Phenol / Phenylpropane / Stilbene
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
10BI795R7D
CAS number
84-16-2
InChI Key
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

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. [Article]
PubChem Compound
192197
PubChem Substance
99444402
ChemSpider
166848
BindingDB
50214281
ChEMBL
CHEMBL9225
ZINC
ZINC000000056547
PDBe Ligand
HXS
Wikipedia
Hexestrol
PDB Entries
3cv6

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)185U.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 FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-1930000000-035978e5e68920c304e8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-059i-0920000000-a03c75f159d7d9de12e5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-5be4258ce82259b29e95
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0012-5910000000-797285d099c5a4bc10e2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-0290000000-4ba63bb1904390022176
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1910000000-8c9c2a9fea3da872610e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006t-2940000000-79ff7caf4625c4d0893f
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]-177.141086
predicted
DarkChem Lite v0.1.0
[M-H]-180.1893473
predicted
DarkChem Lite v0.1.0
[M-H]-168.2235
predicted
DeepCCS 1.0 (2019)
[M+H]+182.5069581
predicted
DarkChem Lite v0.1.0
[M+H]+185.8735473
predicted
DarkChem Lite v0.1.0
[M+H]+170.5815
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.90126
predicted
DarkChem Lite v0.1.0
[M+Na]+181.1736473
predicted
DarkChem Lite v0.1.0
[M+Na]+177.09421
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Aldo-keto reductase family 1 member C1
Kind
Protein
Organism
Humans
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 in...
Gene Name
AKR1C1
Uniprot ID
Q04828
Uniprot Name
Aldo-keto reductase family 1 member C1
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. [Article]
Details2. Estrogen receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Maru BS, Tobias JH, Rivers C, Caunt CJ, Norman MR, McArdle CA: Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. Bone. 2009 Jan;44(1):102-12. doi: 10.1016/j.bone.2008.09.016. Epub 2008 Oct 11. [Article]
Details3. Nuclear receptor subfamily 1 group I member 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [Article]
Details4. Nuclear receptor subfamily 1 group I member 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Agonist at the canonical form of the receptor and at isoform 3 of the receptor.
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [Article]

Drug created at September 15, 2010 21:27 / Updated at December 02, 2023 07:01