Denibulin
Identification
- Generic Name
- Denibulin
- DrugBank Accession Number
- DB05932
- Background
Denibulin is a novel small molecule Vascular Disrupting Agent under development by MediciNova for treatment of solid tumor cancers.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 385.44
Monoisotopic: 385.120860666 - Chemical Formula
- C18H19N5O3S
- Synonyms
- Denibulin
- External IDs
- MN 029
- MN-029
Pharmacology
- Indication
Investigated for use/treatment in solid tumors.
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- Pharmacodynamics
Not Available
- Mechanism of action
Denibulin selectively disrupts newly-formed tumor blood vessels, shutting down tumor blood flow and causing central necrosis of solid tumors. Consistent with its proposed mechanism of action, denibulin has been shown to reduce tumor blood flow resulting in tumor cell necrosis in rats bearing a human lung tumor xenograft. The present Phase I study now extends these findings (reductions in tumor blood flow) to cancer patients.
Target Actions Organism UVascular endothelial growth factor A Not Available Humans UVascular endothelial growth factor receptor 1 Not Available Humans UVascular endothelial growth factor receptor 3 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Denibulin hydrochloride 0U575HR16Q 779356-64-8 JUMSCXLBFWHCRA-PPHPATTJSA-N
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- K7037M241U
- CAS number
- 284019-34-7
- InChI Key
- GAOHLWCIAJNSEE-JTQLQIEISA-N
- InChI
- InChI=1S/C18H19N5O3S/c1-10(19)16(24)20-11-3-5-12(6-4-11)27-13-7-8-14-15(9-13)22-17(21-14)23-18(25)26-2/h3-10H,19H2,1-2H3,(H,20,24)(H2,21,22,23,25)/t10-/m0/s1
- IUPAC Name
- methyl N-[5-({4-[(2S)-2-aminopropanamido]phenyl}sulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
- SMILES
- COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=C(NC(=O)[C@H](C)N)C=C1)=C2
References
- General References
- Not Available
- External Links
- ChemSpider
- 9836493
- ChEMBL
- CHEMBL2111088
- ZINC
- ZINC000011726215
Clinical Trials
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 0.00768 mg/mL ALOGPS logP 2.8 ALOGPS logP 2.72 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 9.6 Chemaxon pKa (Strongest Basic) 8.21 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 122.13 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 106.33 m3·mol-1 Chemaxon Polarizability 41.34 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes 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 splash10-014r-0009000000-ecd870ac4ee19f76d00b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4r-0009000000-ff9e75ba96b39aa69f99 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0zgr-0129000000-26b1ea62680e736d0907 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f79-2009000000-c33ae36b6c29515d927a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1219000000-3062e6fd2bb6e0bc77c9 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0019-3096000000-47d69ef796cc74ca9a14 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 221.9312 predictedDarkChem Lite v0.1.0 [M+H]+ 222.3251 predictedDarkChem Lite v0.1.0 [M+Na]+ 221.586 predictedDarkChem Lite v0.1.0
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vascular endothelial growth factor receptor binding
- Specific Function
- Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of...
- Gene Name
- VEGFA
- Uniprot ID
- P15692
- Uniprot Name
- Vascular endothelial growth factor A
- Molecular Weight
- 27042.205 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vegf-b-activated receptor activity
- Specific Function
- Tyrosine-protein kinase that acts as a cell-surface receptor for VEGFA, VEGFB and PGF, and plays an essential role in the development of embryonic vasculature, the regulation of angiogenesis, cell ...
- Gene Name
- FLT1
- Uniprot ID
- P17948
- Uniprot Name
- Vascular endothelial growth factor receptor 1
- Molecular Weight
- 150767.185 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vascular endothelial growth factor-activated receptor activity
- Specific Function
- Tyrosine-protein kinase that acts as a cell-surface receptor for VEGFC and VEGFD, and plays an essential role in adult lymphangiogenesis and in the development of the vascular network and the cardi...
- Gene Name
- FLT4
- Uniprot ID
- P35916
- Uniprot Name
- Vascular endothelial growth factor receptor 3
- Molecular Weight
- 152755.94 Da
Drug created at November 18, 2007 18:28 / Updated at February 21, 2021 18:51