Obatoclax

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

Identification

Name
Obatoclax
Accession Number
DB12191  (DB05567)
Type
Small Molecule
Groups
Investigational
Description

Obatoclax has been used in trials studying the treatment of AML, Leukemia, Myelofibrosis, Hodgkin's Lymphoma, and Mantle-Cell Lymphoma, among others.

Structure
Thumb
Synonyms
Not Available
External IDs
GX15-070
Product Ingredients
IngredientUNIICASInChI Key
Obatoclax mesylate39200FJ43J803712-79-0ZFKXDVMHNXPEIY-PEZBNFGJSA-N
Categories
Not Available
UNII
QN4128B52A
CAS number
803712-67-6
Weight
Average: 317.392
Monoisotopic: 317.152812244
Chemical Formula
C20H19N3O
InChI Key
RFTSSZJZXOSICM-GRSHGNNSSA-N
InChI
InChI=1S/C20H19N3O/c1-12-8-13(2)21-16(12)10-19-20(24-3)11-18(23-19)17-9-14-6-4-5-7-15(14)22-17/h4-11,21-22H,1-3H3/b19-10-
IUPAC Name
2-[(2Z)-2-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-3-methoxy-2H-pyrrol-5-yl]-1H-indole
SMILES
COC1=CC(=N\C1=C/C1=C(C)C=C(C)N1)C1=CC2=CC=CC=C2N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

Obatoclax binds anti-apoptotic Bcl-2 proteins and interferes with their ability to interact with pro-apoptotic proteins.

TargetActionsOrganism
UApoptosis regulator Bcl-2Not AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11404337
PubChem Substance
347828476
ChemSpider
21430401
BindingDB
50376902
ChEMBL
CHEMBL408194
Wikipedia
Obatoclax

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentChronic Lymphocytic Leukaemia (CLL)1
1CompletedTreatmentHaematological Malignancies1
1TerminatedTreatmentAcute Leukemias of Ambiguous Lineage / Acute Undifferentiated Leukemia (AUL) / Angioimmunoblastic T-Cell Lymphoma / Blastic Phase Chronic Myelogenous Leukemia / Childhood Burkitt Lymphoma / Childhood Chronic Myelogenous Leukemia / Childhood Diffuse Large Cell Lymphoma / Childhood Immunoblastic Large Cell Lymphoma / Childhood Nasal Type Extranodal NK/T-cell Lymphoma / Chronic Lymphocytic Leukemia (CLL) - Refractory / Cutaneous B-Cell Non-Hodgkin Lymphoma / Hepatosplenic T-Cell Lymphoma / Intraocular Lymphoma / Noncutaneous Extranodal Lymphoma / Peripheral T-Cell Lymphoma (PTCL) / Recurrent Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Recurrent Childhood Anaplastic Large Cell Lymphoma / Recurrent Childhood Grade III Lymphomatoid Granulomatosis / Recurrent Childhood Large Cell Lymphoma / Recurrent Childhood Lymphoblastic Lymphoma / Recurrent Childhood Small Noncleaved Cell Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent/Refractory Childhood Hodgkin Lymphoma / Refractory Hairy Cell Leukemia / Relapsing Chronic Myelogenous Leukemia / Small Intestine Lymphoma / Unspecified Childhood Solid Tumor, Protocol Specific1
1TerminatedTreatmentAdult Non-Hodgkin's Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Small Lymphocytic Lymphoma1
1TerminatedTreatmentB-Cell Chronic Lymphocytic Leukemia / Chronic Lymphocytic Leukemia (CLL) - Refractory / Leukemia, Prolymphocytic / Leukemias / Stage I Chronic Lymphocytic Leukemia / Stage II Chronic Lymphocytic Leukemia / Stage III Chronic Lymphocytic Leukemia / Stage IV Chronic Lymphocytic Leukemia1
1, 2CompletedTreatmentExtensive-Stage Small Cell Lung Cancer1
1, 2CompletedTreatmentLung Cancers1
1, 2CompletedTreatmentMantle Cell Lymphoma (MCL)1
1, 2CompletedTreatmentRefractory Small cell lung cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2TerminatedTreatmentMetastatic Melanoma1
1, 2TerminatedTreatmentRefractory Multiple Myeloma / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
1, 2WithdrawnTreatmentExtranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Nodal marginal zone B-cell lymphomas / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Splenic Marginal Zone Lymphoma1
2CompletedTreatmentAgnogenic Myeloid Metaplasia1
2CompletedTreatmentFollicular Lymphoma (FL)1
2CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2CompletedTreatmentLymphoma, Hodgkins1
2CompletedTreatmentMyelodysplastic Syndromes1
2TerminatedTreatmentLeukemias / Systemic Mastocytosis1

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00402 mg/mLALOGPS
logP4.15ALOGPS
logP3.14ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)4.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.17 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.22 m3·mol-1ChemAxon
Polarizability37.3 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 dipyrrins. These are compounds containing two pyrrole rings fused via a methine (-C=) group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrroles
Sub Class
Substituted pyrroles
Direct Parent
Dipyrrins
Alternative Parents
Indoles / Benzenoids / Heteroaromatic compounds / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organooxygen compounds / Hydrocarbon derivatives
Substituents
Dipyrrin / Indole / Indole or derivatives / Benzenoid / Heteroaromatic compound / Ketimine / Azacycle / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. Li J, Viallet J, Haura EB: A small molecule pan-Bcl-2 family inhibitor, GX15-070, induces apoptosis and enhances cisplatin-induced apoptosis in non-small cell lung cancer cells. Cancer Chemother Pharmacol. 2008 Mar;61(3):525-34. Epub 2007 May 16. [PubMed:17505826]
  2. Perez-Galan P, Roue G, Villamor N, Campo E, Colomer D: The BH3-mimetic GX15-070 synergizes with bortezomib in mantle cell lymphoma by enhancing Noxa-mediated activation of Bak. Blood. 2007 May 15;109(10):4441-9. Epub 2007 Jan 16. [PubMed:17227835]

Drug created on October 20, 2016 15:34 / Updated on November 02, 2018 09:03