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- Withdrawn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
Structure for Hexestrol (DB07931)
- 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
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAldo-keto reductase family 1 member C1 Not Available Humans UEstrogen receptor alpha Not Available Humans UNuclear receptor subfamily 1 group I member 2 Not Available Humans UNuclear receptor subfamily 1 group I member 3 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab Hexestrol may decrease the anticoagulant activities of Abciximab. Aceclofenac Aceclofenac may increase the thrombogenic activities of Hexestrol. Acenocoumarol Hexestrol may decrease the anticoagulant activities of Acenocoumarol. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Hexestrol. Adalimumab Hexestrol may increase the thrombogenic activities of Adalimumab. Aducanumab Hexestrol may increase the thrombogenic activities of Aducanumab. Alemtuzumab Hexestrol may increase the thrombogenic activities of Alemtuzumab. Alirocumab Hexestrol may increase the thrombogenic activities of Alirocumab. Allantoin The therapeutic efficacy of Allantoin can be decreased when used in combination with Hexestrol. Alteplase Hexestrol may decrease the anticoagulant activities of Alteplase. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Hexestrol diphosphate sodium VK60X9E36E 171399-06-7 DNCWQZVLWAEATB-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
- 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]
- External Links
- PubChem Compound
- 192197
- PubChem Substance
- 99444402
- ChemSpider
- 166848
- BindingDB
- 50214281
- ChEMBL
- CHEMBL9225
- ZINC
- ZINC000000056547
- PDBe Ligand
- HXS
- Wikipedia
- Hexestrol
- PDB Entries
- 3cv6
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 185 U.S. Patent 2,357,985; U.S. Patent 2,421,401. - Predicted Properties
Property Value Source Water Solubility 0.0139 mg/mL ALOGPS logP 4.98 ALOGPS logP 5.37 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 9.93 Chemaxon pKa (Strongest Basic) -5.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 82.66 m3·mol-1 Chemaxon Polarizability 31.31 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9959 Blood Brain Barrier + 0.7575 Caco-2 permeable + 0.8705 P-glycoprotein substrate Non-substrate 0.5375 P-glycoprotein inhibitor I Non-inhibitor 0.8556 P-glycoprotein inhibitor II Non-inhibitor 0.8622 Renal organic cation transporter Non-inhibitor 0.8652 CYP450 2C9 substrate Non-substrate 0.7865 CYP450 2D6 substrate Non-substrate 0.8813 CYP450 3A4 substrate Non-substrate 0.602 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Non-inhibitor 0.7855 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.5469 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8156 Ames test Non AMES toxic 0.9648 Carcinogenicity Non-carcinogens 0.6254 Biodegradation Not ready biodegradable 0.9528 Rat acute toxicity 1.9859 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8238 hERG inhibition (predictor II) Non-inhibitor 0.5976
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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 March 03, 2023 17:48