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

Identification

Name
TAS-108
Accession Number
DB05966
Description
Not Available
Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 697.866
Monoisotopic: 697.382596975
Chemical Formula
C39H55NO10
Synonyms
Not Available

Pharmacology

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Indication

Investigated for use/treatment in breast cancer.

Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics
Not Available
Mechanism of action

TAS-108 binds to and inhibits estrogenic receptor alpha (ERa), mainly expressed in the mammary gland and uterus and upregulated in estrogen-dependent tumors. Blockage of ERa by TAS-108 prevents the binding and effects of estrogen and may lead to an inhibition of estrogen-dependent cancer cell proliferation. TAS-108 also is a partial agonist of the estrogenic receptor beta (ERb), expressed in many tissues including the central nervous system, urogenital tract, bone and cardiovascular system, thereby exerting a positive effect on these tissues. In addition, TAS-108 activates the co-repressor Silencing Mediator for Retinoid and Thyroid hormone receptor (SMRT), a protein that inhibits the activities of the estrogen receptors, which may contribute to the antitumor activity of TAS-108.

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
Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
3-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / Tricarboxylic acids and derivatives / Anisoles / Benzylamines / Methoxybenzenes / Phenoxy compounds / Phenylmethylamines / Aralkylamines
show 9 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-hydroxysteroid / Alcohol / Alkyl aryl ether / Alpha-hydroxy acid / Amine / Anisole / Aralkylamine / Aromatic homopolycyclic compound / Benzenoid
show 26 more
Molecular Framework
Not Available
External Descriptors
Not Available

Chemical Identifiers

UNII
9B29N23K7E
CAS number
229634-97-3
InChI Key
VOHOCSJONOJOSD-SCIDSJFVSA-N
InChI
InChI=1S/C33H47NO3.C6H8O7/c1-6-34(7-2)21-23-8-13-30(31(19-23)36-5)37-17-15-25-9-12-29-32-22(3)18-24-20-26(35)10-11-27(24)28(32)14-16-33(25,29)4;7-3(8)1-6(13,5(11)12)2-4(9)10/h8,10-11,13,19-20,22,25,28-29,32,35H,6-7,9,12,14-18,21H2,1-5H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t22-,25-,28-,29+,32-,33-;/m1./s1
IUPAC Name
(1S,9R,10S,11S,14R,15R)-14-(2-{4-[(diethylamino)methyl]-2-methoxyphenoxy}ethyl)-9,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-ol; 2-hydroxypropane-1,2,3-tricarboxylic acid
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.CCN(CC)CC1=CC=C(OCC[C@H]2CC[C@H]3[C@@H]4[C@H](C)CC5=C(C=CC(O)=C5)[C@H]4CC[C@]23C)C(OC)=C1

References

General References
  1. Buzdar AU: TAS-108: a novel steroidal antiestrogen. Clin Cancer Res. 2005 Jan 15;11(2 Pt 2):906s-8s. [PubMed:15701885]
  2. Yamamoto Y, Shibata J, Yonekura K, Sato K, Hashimoto A, Aoyagi Y, Wierzba K, Yano S, Asao T, Buzdar AU, Terada T: TAS-108, a novel oral steroidal antiestrogenic agent, is a pure antagonist on estrogen receptor alpha and a partial agonist on estrogen receptor beta with low uterotrophic effect. Clin Cancer Res. 2005 Jan 1;11(1):315-22. [PubMed:15671561]
ChemSpider
8050563
Wikipedia
TAS-108

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentBreast 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 Solubility3.66e-05 mg/mLALOGPS
logP7.47ALOGPS
logP7.18ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)10.34ChemAxon
pKa (Strongest Basic)9.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity152.78 m3·mol-1ChemAxon
Polarizability62.51 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
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

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
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 November 18, 2007 18:29 / Updated on June 12, 2020 16:52