Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H24O4 |
Molecular Weight | 328.4022 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 7 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(\C=C\C=C(/C)C(O)=O)=C/C=C/C=C(C)/C=C/C=C(\C)C(O)=O
InChI
InChIKey=PANKHBYNKQNAHN-MQQNZMFNSA-N
InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+
Molecular Formula | C20H24O4 |
Molecular Weight | 328.4022 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 7 |
Optical Activity | NONE |
Transcrocetinate (TSC) is a novel compound that offers promise as a treatment for conditions caused by hypoxia or ischemia. Unlike crocetin, it worked well in the more severe hemorrhagic shock model. Although many of the earlier studies with TSC involved the treatment of the ischemic conditions of hemorrhagic shock in both rats and swine, a few other studies involved treating purely hypoxic situations. One study showed that TSC was capable of promoting survival in rats breathing 10% oxygen. TSC also was able to increase arterial PO2 values in a rat model of acute respiratory distress syndrome (ARDS) caused by injection of oleic acid. The drug acts via a mechanism that has not been previously exploited in a pharmaceutical. TSC increases the rate of oxygen diffusion between the erythrocytes and the tissues by altering the 'structure' of water in blood plasma. It does this by causing additional hydrogen bonds to form among the water molecules. Animal toxicology studies have demonstrated that high levels of TSC are well-tolerated, and a Phase I clinical study has shown that TSC is also safe in humans. Delayed TSC treatment improves outcomes in experimental models of both ischemic and hemorrhagic stroke. TSC may be a safe and beneficial therapeutic modality for early stroke intervention, irrespective of the type of stroke involved. Transcrocetinate is in phase III clinical trial for the treatment of glioblastoma.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16038536 |
28.0 µM [IC50] |
PubMed
Title | Date | PubMed |
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Trans-sodium crocetinate for treating hypoxia/ischemia. | 2008 Jun |
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Effect of trans sodium crocetinate on brain tumor oxygenation. Laboratory investigation. | 2009 Aug |
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Trans-sodium crocetinate enhancing survival and glioma response on magnetic resonance imaging to radiation and temozolomide. | 2010 Aug |
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Evaluation of trans sodium crocetinate on safety and exercise performance in patients with peripheral artery disease and intermittent claudication. | 2011 Oct |
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Trans sodium crocetinate: functional neuroimaging studies in a hypoxic brain tumor. | 2011 Oct |
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Perihematomal Cellular Injury Is Reduced by Trans-sodium Crocetinate in a Model of Intracerebral Hemorrhage. | 2015 Oct |
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Trans sodium crocetinate with temozolomide and radiation therapy for glioblastoma multiforme. | 2017 Feb |
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Trans sodium crocetinate alleviates ischemia/reperfusion-induced myocardial oxidative stress and apoptosis via the SIRT3/FOXO3a/SOD2 signaling pathway. | 2019 Jun |
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 16:04:48 GMT 2023
by
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on
Sat Dec 16 16:04:48 GMT 2023
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Record UNII |
20TC155L9C
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C68303
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C152713
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CROCETIN
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504-39-2
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m3849
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SALT/SOLVATE -> PARENT |
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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ACTIVE MOIETY |
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