Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H45NO |
| Molecular Weight | 399.6523 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=C\C(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=N/O)[C@H](C)CCCC(C)C
InChI
InChIKey=QNTASHOAVRSLMD-FCARAQADSA-N
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
| Molecular Formula | C27H45NO |
| Molecular Weight | 399.6523 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Olesoxime (TRO19622) a small-molecule with a cholesterol-like structure has remarkable neuroprotective properties for motor neurons in cell culture and in rodents. The biopharmaceutical company Trophos initially developed this compound. This medicine is in phase II clinical trial in treating spinal muscular atrophy and in phase I for patients with stable relapsing remitting multiple sclerosis. This drug was also investigated in phase III clinical trial for amyotrophic lateral sclerosis, but it did not demonstrate a significant increase in survival versus placebo and that study was discontinued. Preclinical studies have demonstrated that the olesoxime promoted the function and survival of neurons and other cell types under disease-relevant stress conditions through interactions with the mitochondrial permeability transition pore (mPTP).
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Identification and characterization of cholest-4-en-3-one, oxime (TRO19622), a novel drug candidate for amyotrophic lateral sclerosis. | 2007 Aug |
|
| Specific antinociceptive activity of cholest-4-en-3-one, oxime (TRO19622) in experimental models of painful diabetic and chemotherapy-induced neuropathy. | 2008 Aug |
|
| Dysfunction of mitochondria and sarcoplasmic reticulum in the pathogenesis of collagen VI muscular dystrophies. | 2008 Dec |
|
| Olesoxime (cholest-4-en-3-one, oxime): analgesic and neuroprotective effects in a rat model of painful peripheral neuropathy produced by the chemotherapeutic agent, paclitaxel. | 2009 Dec 15 |
|
| Mitochondrial calcium and the permeability transition in cell death. | 2009 Nov |
|
| Olesoxime, a cholesterol-like neuroprotectant for the potential treatment of amyotrophic lateral sclerosis. | 2010 Aug |
|
| Clinical trials in CNS--SMi's eighth annual conference. | 2010 Feb |
|
| Olesoxime prevents microtubule-targeting drug neurotoxicity: selective preservation of EB comets in differentiated neuronal cells. | 2010 Sep 15 |
Patents
Sample Use Guides
Participants will receive 10 milligrams per kilogram (mg/kg) suspension once a day either orally or via a naso-gastric or gastrostomy tube with the main meal (preferably at the same time of the day)
Route of Administration:
Oral
Neuroprotective dose-effect of olesoxime against motor neuron cell death was studied. Rat embryonic motor neurons were cultured in 96-well plates in the absence of trophic factors and with increasing concentrations of olesoxime (concentrations ranging from 0.1 to 10 µM), or with pure syn or anti forms of olesoxime. Motor neuron survival was measured after 3 days or 7 days in vitro by direct counting of live cells labeled with calcein-AM. Survival is expressed as a ratio of surviving cell (A-B) relative to positive controls treated with a cocktail of neurotrophic factors (NTFs) and negative controls that received DMSO alone (0.1%). Treatment with olesoxime produced a dose-dependent increase in cell survival with EC50 around 3 µM. Importantly, both syn and anti forms were equally potent.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:20:37 GMT 2023
by
admin
on
Fri Dec 15 16:20:37 GMT 2023
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| Record UNII |
I2QN18P645
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| Record Status |
Validated (UNII)
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| Record Version |
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66514-00-9
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admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
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I2QN18P645
Created by
admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
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