NAV

Dexanabinol

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

Identification

Generic Name
Dexanabinol
DrugBank Accession Number
DB06444
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 386.576
Monoisotopic: 386.282095084
Chemical Formula
C25H38O3
Synonyms
  • Sinnabidol
External IDs
  • (+)-HU-210
  • HU-211
  • PA-50211
  • PRS-211007
  • PRS-211007-000
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Pharmacology

Indication

Investigated for use/treatment in traumatic brain injuries and neurologic disorders.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTumor necrosis factorNot 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

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
2,2-dimethyl-1-benzopyrans
Alternative Parents
Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Oxacyclic compounds / Primary alcohols / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2,2-dimethyl-1-benzopyran / Alcohol / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenoid / Ether / Hydrocarbon derivative / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
R6VT8U5372
CAS number
112924-45-5
InChI Key
SSQJFGMEZBFMNV-PMACEKPBSA-N
InChI
InChI=1S/C25H38O3/c1-6-7-8-9-12-24(2,3)18-14-21(27)23-19-13-17(16-26)10-11-20(19)25(4,5)28-22(23)15-18/h10,14-15,19-20,26-27H,6-9,11-13,16H2,1-5H3/t19-,20-/m0/s1
IUPAC Name
(6aS,10aS)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol
SMILES
CCCCCCC(C)(C)C1=CC(O)=C2[C@H]3CC(CO)=CC[C@@H]3C(C)(C)OC2=C1

References

General References
Not Available
PubChem Compound
107778
PubChem Substance
347827772
ChemSpider
96934
BindingDB
50067498
ChEMBL
CHEMBL334533
ZINC
ZINC000003799010
Wikipedia
Dexanabinol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentTraumatic Brain Injury (TBI)1
1CompletedBasic ScienceCancer / Pharmacokinetics / Safety / Tolerability1
1CompletedTreatmentBrain Cancer1
1CompletedTreatmentSolid Tumors1
1Unknown StatusTreatmentHepatocellular Carcinoma / Pancreatic Cancer1

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 Solubility0.00148 mg/mLALOGPS
logP8.03ALOGPS
logP6.14Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)9.98Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.69 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity116.73 m3·mol-1Chemaxon
Polarizability47.4 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-000i-6009000000-e16143d07e17d4684b92
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-f630c0725022f9f034ab
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-3039000000-d14f2b0a1dc85cfe2268
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-d31e67f666d4d50b68a9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-029i-0039000000-d7ae58e07c50977da043
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5c-9003000000-ea9c47c2fee033baaae5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-213.2283692
predicted
DarkChem Lite v0.1.0
[M-H]-209.81049
predicted
DeepCCS 1.0 (2019)
[M+H]+208.9202692
predicted
DarkChem Lite v0.1.0
[M+H]+212.16849
predicted
DeepCCS 1.0 (2019)
[M+Na]+209.3484692
predicted
DarkChem Lite v0.1.0
[M+Na]+219.73604
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Tumor necrosis factor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
References
  1. Leker RR, Shohami E, Abramsky O, Ovadia H: Dexanabinol; a novel neuroprotective drug in experimental focal cerebral ischemia. J Neurol Sci. 1999 Jan 15;162(2):114-9. [Article]
  2. Trembovler V, Abu-Raya S, Shohami E: Synergism between tumor necrosis factor-alpha and H2O2 enhances cell damage in rat PC12 cells. Neurosci Lett. 2003 Dec 19;353(2):115-8. [Article]

Drug created at March 19, 2008 16:33 / Updated at June 12, 2020 16:52