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Olesoxime

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Identification

Generic Name
Olesoxime
DrugBank Accession Number
DB05185
Background

Olesoxime is a cholesterol-like small molecule that has demonstrated a remarkable neuroprotective profile in a battery of both in vitro and in vivo preclinical models. For example, it has demonstrated the ability to prevent neurodegeneration, enhance nerve function and accelerate neuroregeneration following nerve trauma.1,2

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 399.663
Monoisotopic: 399.350115073
Chemical Formula
C27H45NO
Synonyms
  • (EZ)-N-(CHOLEST-4-EN-3-YLIDENE)HYDROXYLAMINE
  • 4-Cholesten-3-one, oxime
  • cholest-4-en-3-one, oxime
External IDs
  • TRO 19622
  • TRO-19622
  • TRO19622
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Pharmacology

Indication

Investigated for use/treatment in neurologic disorders.

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Pharmacodynamics

Not Available

Mechanism of action

Olesoxime interacts with a physiologically relevant target: the mitochondrial permeability transition pore (mPTP). Mitochondria are central mediators of cell death and are implicated in most if not all neurodegenerative diseases regardless of the initiating factor: genetic mutations, excitotoxicity, reactive oxygen species, ischemia, chemical toxicity, etc. Mitochondria play diverse roles in all cells. In neurons, especially near synaptic sites, mitochondria are essential calcium-buffering organelles in areas where membrane excitability leads to large influx of calcium through calcium channels. Mitochondria also produce the ATP necessary for microtubule-based axoplasmic transport and maintaining the activity of ion and nutrient transporters. If a neuron fails to establish or maintain its functional role, mitochondria are responsible for eliminating it by releasing apoptotic factors. Olesoxime, by interacting with protein components of the mPTP, prevents the release of these apoptotic factors and therefore protects the neuron. This mechanism of action may lead to a general neuroprotective activity with utility in other therapeutic indications.

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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
8V8EF6094N
CAS number
22033-87-0
InChI Key
QNTASHOAVRSLMD-SIWSWZRQSA-N
InChI
InChI=1S/C27H45NO/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28-29)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25,29H,6-16H2,1-5H3/b28-21+/t19-,22+,23-,24+,25+,26+,27-/m1/s1
IUPAC Name
N-[(1R,3aS,3bS,7E,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ylidene]hydroxylamine
SMILES
[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CCC4=C\C(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=N\O

References

General References
  1. Bordet T, Buisson B, Michaud M, Drouot C, Galea P, Delaage P, Akentieva NP, Evers AS, Covey DF, Ostuni MA, Lacapere JJ, Massaad C, Schumacher M, Steidl EM, Maux D, Delaage M, Henderson CE, Pruss RM: Identification and characterization of cholest-4-en-3-one, oxime (TRO19622), a novel drug candidate for amyotrophic lateral sclerosis. J Pharmacol Exp Ther. 2007 Aug;322(2):709-20. Epub 2007 May 11. [Article]
  2. Bordet T, Berna P, Abitbol JL, Pruss RM: Olesoxime (TRO19622): A Novel Mitochondrial-Targeted Neuroprotective Compound. Pharmaceuticals (Basel). 2010 Jan 28;3(2):345-368. doi: 10.3390/ph3020345. [Article]
PubChem Substance
347910009
ChemSpider
8106458
ZINC
ZINC000100657483
Wikipedia
Olesoxime

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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3CompletedOtherAmyotrophic Lateral Sclerosis (ALS)1somestatusstop reasonjust information to hide
2CompletedTreatmentChemotherapy Induced Peripheral Neuropathy (CIPN)1somestatusstop reasonjust information to hide
2CompletedTreatmentMuscular Atrophy, Spinal, Type II / Spinal Muscular Atrophy Type III Non Ambulant1somestatusstop reasonjust information to hide
2CompletedTreatmentNon-Alcoholic Steatohepatitis (NASH)1somestatusstop reasonjust information to hide
2CompletedTreatmentSpinal Muscular Atrophy (SMA)1somestatusstop reasonjust information to hide

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 Solubility0.000102 mg/mLALOGPS
logP6.54ALOGPS
logP7.69Chemaxon
logS-6.6ALOGPS
pKa (Strongest Acidic)11.46Chemaxon
pKa (Strongest Basic)3.37Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area32.59 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity123.39 m3·mol-1Chemaxon
Polarizability51.56 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at October 21, 2007 22:24 / Updated at July 18, 2023 22:56