NAV

Denibulin

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

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
3D
Similar Structures
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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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
UVascular endothelial growth factor ANot AvailableHumans
UVascular endothelial growth factor receptor 1Not AvailableHumans
UVascular endothelial growth factor receptor 3Not 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
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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
Denibulin hydrochloride0U575HR16Q779356-64-8JUMSCXLBFWHCRA-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
ChemSpider
9836493
ChEMBL
CHEMBL2111088
ZINC
ZINC000011726215

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00768 mg/mLALOGPS
logP2.8ALOGPS
logP2.72Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.6Chemaxon
pKa (Strongest Basic)8.21Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area122.13 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity106.33 m3·mol-1Chemaxon
Polarizability41.34 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Details1. Vascular endothelial growth factor A
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
Details2. Vascular endothelial growth factor receptor 1
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
Details3. Vascular endothelial growth factor receptor 3
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