This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Enzastaurin
- DrugBank Accession Number
- DB06486
- Background
Enzastaurin, an investigational, targeted, oral agent, will be evaluated at more than 100 sites worldwide for the treatment of relapsed glioblastoma multiforme (GBM), an aggressive and malignant form of brain cancer.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Enzastaurin (DB06486)
- Weight
- Average: 515.617
Monoisotopic: 515.232125194 - Chemical Formula
- C32H29N5O2
- Synonyms
- Enzastaurin
- External IDs
- LY-317615
- LY317615
Pharmacology
- Indication
Investigated for use/treatment in brain cancer, lymphoma (non-hodgkin's), and lung cancer.
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Not Available
- Mechanism of action
Enzastaurin is an oral serine-threonine kinase inhibitor that is designed to suppress tumor growth through multiple mechanisms. Preclinical data indicate it may reduce the cell's ability to reproduce (cell proliferation), increase the natural death of the tumor cells (apoptosis), and inhibit tumor- induced blood supply (angiogenesis). Enzastaurin has been shown to inhibit signaling through the PKC-B and PI3K/AKT pathways. These pathways have been shown to be activated in a wide variety of cancers. In addition to glioblastoma, enzastaurin is also being studied in multiple other tumor types, including non-Hodgkin's lymphoma, colorectal cancer, non-small cell lung cancer, pancreatic cancer, and mantle cell lymphoma.
Target Actions Organism UProtein kinase C beta type Not Available Humans UAurora kinase B Not Available Humans UAurora kinase A Not Available Humans UCyclin-dependent kinase 15 Not Available Humans USerine/threonine-protein kinase Chk1 Not Available Humans USerine/threonine-protein kinase Chk2 Not Available Humans URAC-alpha serine/threonine-protein kinase Not Available Humans UPhosphatidylinositol 3-kinase regulatory subunit alpha Not Available Humans - 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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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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Ingredient UNII CAS InChI Key Enzastaurin Hydrochloride KX7K68Z2UH 359017-79-1 UUADYKVKJIMIPA-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- N-alkylindoles
- Direct Parent
- N-alkylindoles
- Alternative Parents
- Indoles / 2-pyridylmethylamines / Aralkylamines / Maleimides / Benzenoids / Piperidines / N-methylpyrroles / Heteroaromatic compounds / Dicarboximides / Pyrrolines show 8 more
- Substituents
- 2-pyridylmethylamine / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- UC96G28EQF
- CAS number
- 170364-57-5
- InChI Key
- AXRCEOKUDYDWLF-UHFFFAOYSA-N
- InChI
- InChI=1S/C32H29N5O2/c1-35-19-25(23-9-2-4-11-27(23)35)29-30(32(39)34-31(29)38)26-20-37(28-12-5-3-10-24(26)28)22-13-16-36(17-14-22)18-21-8-6-7-15-33-21/h2-12,15,19-20,22H,13-14,16-18H2,1H3,(H,34,38,39)
- IUPAC Name
- 3-(1-methyl-1H-indol-3-yl)-4-(1-{1-[(pyridin-2-yl)methyl]piperidin-4-yl}-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
- SMILES
- CN1C=C(C2=CC=CC=C12)C1=C(C(=O)NC1=O)C1=CN(C2CCN(CC3=CC=CC=N3)CC2)C2=CC=CC=C12
References
- General References
- Not Available
- External Links
- ChemSpider
- 153463
- BindingDB
- 50128285
- ChEBI
- 91368
- ChEMBL
- CHEMBL300138
- ZINC
- ZINC000001494900
- Wikipedia
- Enzastaurin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Active Not Recruiting Treatment Glioblastoma Multiforme (GBM) 1 3 Completed Prevention Non-Hodgkin's Lymphoma (NHL) 1 3 Completed Treatment Diffuse Large B-Cell Lymphoma (DLBCL) 1 3 Completed Treatment Glioblastoma Multiforme (GBM) 1 3 Suspended Prevention Vascular Ehlers Danlos Syndrome 1 2 Completed Prevention Lung Cancer 1 2 Completed Treatment Abdominal wall neoplasm / Fallopian Tube Neoplasms / Ovarian Cancer 1 2 Completed Treatment B-Cell Lymphoma / T-cell type lymphoma 1 2 Completed Treatment Breast Cancer 1 2 Completed Treatment Breast Neoplasms 1
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
Property Value Source Water Solubility 0.00903 mg/mL ALOGPS logP 4.86 ALOGPS logP 3.96 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 9.71 Chemaxon pKa (Strongest Basic) 7.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 72.16 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 151.61 m3·mol-1 Chemaxon Polarizability 56.74 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase involved in various cellular processes such as regulation of the B-cell receptor (BCR) signalosom...
- Gene Name
- PRKCB
- Uniprot ID
- P05771
- Uniprot Name
- Protein kinase C beta type
- Molecular Weight
- 76868.45 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein serine/threonine/tyrosine kinase activity
- Specific Function
- Serine/threonine-protein kinase component of the chromosomal passenger complex (CPC), a complex that acts as a key regulator of mitosis. The CPC complex has essential functions at the centromere in...
- Gene Name
- AURKB
- Uniprot ID
- Q96GD4
- Uniprot Name
- Aurora kinase B
- Molecular Weight
- 39310.195 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein serine/threonine/tyrosine kinase activity
- Specific Function
- Mitotic serine/threonine kinases that contributes to the regulation of cell cycle progression. Associates with the centrosome and the spindle microtubules during mitosis and plays a critical role i...
- Gene Name
- AURKA
- Uniprot ID
- O14965
- Uniprot Name
- Aurora kinase A
- Molecular Weight
- 45809.03 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein serine/threonine kinase activity
- Specific Function
- Serine/threonine-protein kinase that acts like an antiapoptotic protein that counters TRAIL/TNFSF10-induced apoptosis by inducing phosphorylation of BIRC5 at 'Thr-34'.
- Gene Name
- CDK15
- Uniprot ID
- Q96Q40
- Uniprot Name
- Cyclin-dependent kinase 15
- Molecular Weight
- 49022.64 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein serine/threonine kinase activity
- Specific Function
- Serine/threonine-protein kinase which is required for checkpoint-mediated cell cycle arrest and activation of DNA repair in response to the presence of DNA damage or unreplicated DNA. May also nega...
- Gene Name
- CHEK1
- Uniprot ID
- O14757
- Uniprot Name
- Serine/threonine-protein kinase Chk1
- Molecular Weight
- 54433.115 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Serine/threonine-protein kinase which is required for checkpoint-mediated cell cycle arrest, activation of DNA repair and apoptosis in response to the presence of DNA double-strand breaks. May also...
- Gene Name
- CHEK2
- Uniprot ID
- O96017
- Uniprot Name
- Serine/threonine-protein kinase Chk2
- Molecular Weight
- 60914.26 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein serine/threonine/tyrosine kinase activity
- Specific Function
- AKT1 is one of 3 closely related serine/threonine-protein kinases (AKT1, AKT2 and AKT3) called the AKT kinase, and which regulate many processes including metabolism, proliferation, cell survival, ...
- Gene Name
- AKT1
- Uniprot ID
- P31749
- Uniprot Name
- RAC-alpha serine/threonine-protein kinase
- Molecular Weight
- 55686.035 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane receptor protein tyrosine kinase adaptor activity
- Specific Function
- Binds to activated (phosphorylated) protein-Tyr kinases, through its SH2 domain, and acts as an adapter, mediating the association of the p110 catalytic unit to the plasma membrane. Necessary for t...
- Gene Name
- PIK3R1
- Uniprot ID
- P27986
- Uniprot Name
- Phosphatidylinositol 3-kinase regulatory subunit alpha
- Molecular Weight
- 83597.675 Da
Drug created at March 19, 2008 16:34 / Updated at February 21, 2021 18:52