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

Identification

Generic Name
Obatoclax
DrugBank Accession Number
DB12191
Background

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

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 317.392
Monoisotopic: 317.152812244
Chemical Formula
C20H19N3O
Synonyms
  • Obatoclax
External IDs
  • GX 015-070
  • GX 05-070
  • GX15-070

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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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 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
Adverseeffects
Improve decision support & research outcomes
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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

Products

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Product Ingredients
IngredientUNIICASInChI Key
Obatoclax mesylate39200FJ43J803712-79-0ZFKXDVMHNXPEIY-PEZBNFGJSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Dipyrrin / Heteroaromatic compound / Hydrocarbon derivative / Imine / Indole / Indole or derivatives / Ketimine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
QN4128B52A
CAS number
803712-67-6
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

References

General References
Not Available
PubChem Compound
11404337
PubChem Substance
347828476
ChemSpider
21430401
BindingDB
50376902
ChEMBL
CHEMBL408194
ZINC
ZINC000029052268
Wikipedia
Obatoclax

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3WithdrawnTreatmentExtensive-stage Small Cell Lung Cancer (SCLC)1
2CompletedTreatmentAcute Myeloid Leukemia (AML)1
2CompletedTreatmentAgnogenic Myeloid Metaplasia1
2CompletedTreatmentFollicular Lymphoma ( FL)1
2CompletedTreatmentLymphoma, Hodgkins1
2CompletedTreatmentMyelodysplastic Syndromes (MDS)1
2TerminatedTreatmentLeukemias / Systemic Mastocytosis1
1CompletedTreatmentChronic Lymphocytic Leukemia (CLL)1
1CompletedTreatmentHaematological Malignancies1
1TerminatedTreatmentAcute Leukemias of Ambiguous Lineage / Acute Undifferentiated Leukemia (AUL) / Angioimmunoblastic T-cell Lymphoma (AITL) / 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 / Chronic Myelogenous Leukemia, Blastic Phase / Cutaneous B-Cell Non-Hodgkin Lymphoma / Hepato-splenic 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

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
logP3.14ChemAxon
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
Polarizability37.32 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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at October 20, 2016 21:34 / Updated at February 21, 2021 18:53