Arzoxifene

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Arzoxifene
Accession Number
DB06249
Type
Small Molecule
Groups
Approved, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
LY353381
Product Ingredients
IngredientUNIICASInChI Key
Arzoxifene HydrochlorideFU88PI0433182133-27-3NHSNLUIMAQQXGR-UHFFFAOYSA-N
Categories
UNII
E569WG6E60
CAS number
182133-25-1
Weight
Average: 475.6
Monoisotopic: 475.181729592
Chemical Formula
C28H29NO4S
InChI Key
MCGDSOGUHLTADD-UHFFFAOYSA-N
InChI
InChI=1S/C28H29NO4S/c1-31-22-8-5-20(6-9-22)28-27(25-14-7-21(30)19-26(25)34-28)33-24-12-10-23(11-13-24)32-18-17-29-15-3-2-4-16-29/h5-14,19,30H,2-4,15-18H2,1H3
IUPAC Name
2-(4-methoxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]phenoxy}-1-benzothiophen-6-ol
SMILES
COC1=CC=C(C=C1)C1=C(OC2=CC=C(OCCN3CCCCC3)C=C2)C2=C(S1)C=C(O)C=C2

Pharmacology

Indication

Investigated for use/treatment in breast cancer, osteoporosis, and endometrial cancer.

Pharmacodynamics
Not Available
Mechanism of action

Arzoxifene is a selective estrogen receptor modulator (SERM) which antagonizes estrogen in mammary and uterine tissue, but acts as an estrogen receptor agonist in bone tissue. Arzoxifene reduces bone loss and risk of osteoperosis and decreases serum cholesterol.

TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHumans
UEstrogen receptor betaNot 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
Toxicity
Not Available
Affected organisms
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.
Not Available
Food Interactions
Not Available

References

General References
  1. Suh N, Glasebrook AL, Palkowitz AD, Bryant HU, Burris LL, Starling JJ, Pearce HL, Williams C, Peer C, Wang Y, Sporn MB: Arzoxifene, a new selective estrogen receptor modulator for chemoprevention of experimental breast cancer. Cancer Res. 2001 Dec 1;61(23):8412-5. [PubMed:11731420]
External Links
ChemSpider
156104
BindingDB
19442
ChEMBL
CHEMBL226267
ZINC
ZINC000001544683
Wikipedia
Arzoxifene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentBreast Cancer1
2CompletedPreventionBreast Cancer1
2CompletedPreventionBreast Cancer / Hereditary Breast/Ovarian Cancer (brca1, brca2)1
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentEndometrial Cancer1
2CompletedTreatmentOsteoporosis1
2CompletedTreatmentOvarian Cancer / Primary Peritoneal Cavity Cancer1
3CompletedPreventionPostmenopausal Bone Loss1
3CompletedTreatmentNeoplasms, Breast1
3CompletedTreatmentPostmenopausal Osteoporosis (PMO)2
4CompletedTreatmentBreast Cancer / Endometrial Cancer / Ovarian Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000496 mg/mLALOGPS
logP6.3ALOGPS
logP5.89ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.16 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity135.63 m3·mol-1ChemAxon
Polarizability52.44 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Diarylethers
Alternative Parents
1-benzothiophenes / Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Thiophenes / Heteroaromatic compounds / Trialkylamines
show 3 more
Substituents
Diaryl ether / 1-benzothiophene / Benzothiophene / Phenoxy compound / Anisole / Methoxybenzene / Phenol ether / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da

Drug created on March 19, 2008 10:19 / Updated on June 12, 2020 10:52

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates