Pipendoxifene

Identification

Generic Name
Pipendoxifene
DrugBank Accession Number
DB05414
Background

ER modulator, ERA-923(Pipendoxifene) is a estrogen receptor modulator being evaluated for the treatment of breast cancer. Pipendoxifene is a new 2-phenyl indole selective estrogen receptor modulators (SERM )that exhibits an excellent preclinical pharmacological profile and was selected for further development as a treatment for metastatic breast cancer.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 456.576
Monoisotopic: 456.2412929
Chemical Formula
C29H32N2O3
Synonyms
  • Pipendoxifene
External IDs
  • ERA-923

Pharmacology

Indication

Investigated for use/treatment in breast cancer.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

ERA-923 inhibits estrogen-stimulated growth associated with cytostasis. It has been shown to have a potent, selective oestrogen modulating effect, with few uterine side-effects.

TargetActionsOrganism
UIntegrase, catalytic coreNot AvailableNitrosomonas europaea (strain ATCC 19718 / NBRC 14298)
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
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2-phenylindoles. These are indoles substituted at the 2-position with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
2-phenylindoles
Alternative Parents
Phenylpyrroles / N-alkylindoles / Hydroxyindoles / 3-methylindoles / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Heteroaromatic compounds
show 4 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2-phenylindole / 2-phenylpyrrole / 3-alkylindole / 3-methylindole / Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
TPC5Q8496G
CAS number
198480-55-6
InChI Key
JICOGKJOQXTAIP-UHFFFAOYSA-N
InChI
InChI=1S/C29H32N2O3/c1-21-27-19-25(33)11-14-28(27)31(29(21)23-7-9-24(32)10-8-23)20-22-5-12-26(13-6-22)34-18-17-30-15-3-2-4-16-30/h5-14,19,32-33H,2-4,15-18,20H2,1H3
IUPAC Name
2-(4-hydroxyphenyl)-3-methyl-1-({4-[2-(piperidin-1-yl)ethoxy]phenyl}methyl)-1H-indol-5-ol
SMILES
CC1=C(N(CC2=CC=C(OCCN3CCCCC3)C=C2)C2=C1C=C(O)C=C2)C1=CC=C(O)C=C1

References

General References
Not Available
PubChem Compound
6433099
PubChem Substance
175426998
ChemSpider
4938287
BindingDB
50099587
ChEMBL
CHEMBL44426
ZINC
ZINC000000602799
Wikipedia
Selective_estrogen_receptor_modulator

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentBreast 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 Solubility0.000933 mg/mLALOGPS
logP5.75ALOGPS
logP5.82Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)9.51Chemaxon
pKa (Strongest Basic)8.77Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area57.86 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity137.29 m3·mol-1Chemaxon
Polarizability52.18 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9949
Blood Brain Barrier+0.9022
Caco-2 permeable-0.5514
P-glycoprotein substrateSubstrate0.7583
P-glycoprotein inhibitor IInhibitor0.5899
P-glycoprotein inhibitor IIInhibitor0.9658
Renal organic cation transporterInhibitor0.6989
CYP450 2C9 substrateNon-substrate0.7793
CYP450 2D6 substrateNon-substrate0.5366
CYP450 3A4 substrateSubstrate0.5887
CYP450 1A2 substrateNon-inhibitor0.596
CYP450 2C9 inhibitorNon-inhibitor0.7992
CYP450 2D6 inhibitorNon-inhibitor0.6596
CYP450 2C19 inhibitorNon-inhibitor0.5806
CYP450 3A4 inhibitorInhibitor0.8133
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9384
Ames testNon AMES toxic0.8154
CarcinogenicityNon-carcinogens0.9499
BiodegradationNot ready biodegradable0.9974
Rat acute toxicity2.5457 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5124
hERG inhibition (predictor II)Inhibitor0.8018
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0210900000-48a79dbb28eda9d6d437
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0010900000-91d3114c082b65c1cf89
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3233900000-29c2ffd9e732aee28026
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-1189300000-6161ebbeabb0af7761cf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06rj-7900300000-e8513213773dc36f871d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0092100000-b251cdc0e4dcab720b75
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]-211.60136
predicted
DeepCCS 1.0 (2019)
[M+H]+213.95937
predicted
DeepCCS 1.0 (2019)
[M+Na]+220.89339
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Nitrosomonas europaea (strain ATCC 19718 / NBRC 14298)
Pharmacological action
Unknown
General Function
Nucleic acid binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q81ZL8
Uniprot Name
Integrase, catalytic core
Molecular Weight
37052.215 Da

Drug created at November 18, 2007 18:24 / Updated at February 21, 2021 18:51