Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H22O4.2Na |
| Molecular Weight | 372.3658 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 7 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].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=RMDMBHQVNHQDDD-VFWKRBOSSA-L
InChI=1S/C20H24O4.2Na/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);;/q;2*+1/p-2/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+;;
| Molecular Formula | C20H22O4 |
| Molecular Weight | 326.3863 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 7 |
| Optical Activity | NONE |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| 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 |
|---|---|---|
| Trans sodium crocetinate alleviates ischemia/reperfusion-induced myocardial oxidative stress and apoptosis via the SIRT3/FOXO3a/SOD2 signaling pathway. | 2019-06 |
|
| Trans sodium crocetinate with temozolomide and radiation therapy for glioblastoma multiforme. | 2017-02 |
|
| Perihematomal Cellular Injury Is Reduced by Trans-sodium Crocetinate in a Model of Intracerebral Hemorrhage. | 2015-10 |
|
| Trans-sodium crocetinate provides neuroprotection against cerebral ischemia and reperfusion in obese mice. | 2015-04 |
|
| Trans-sodium crocetinate improves outcomes in rodent models of occlusive and hemorrhagic stroke. | 2014-10-02 |
|
| Evaluation of trans sodium crocetinate on safety and exercise performance in patients with peripheral artery disease and intermittent claudication. | 2011-10 |
|
| Trans sodium crocetinate: functional neuroimaging studies in a hypoxic brain tumor. | 2011-10 |
|
| Metabolic reflow as a therapy for ischemic brain injury. | 2011 |
|
| Protection against focal ischemic injury to the brain by trans-sodium crocetinate. Laboratory investigation. | 2010-10 |
|
| Trans-sodium crocetinate enhancing survival and glioma response on magnetic resonance imaging to radiation and temozolomide. | 2010-08 |
|
| Efficacy and safety profile of the carotenoid trans sodium crocetinate administered to rabbits following multiple infarct ischemic strokes: a combination therapy study with tissue plasminogen activator. | 2010-01-14 |
|
| Effect of trans sodium crocetinate on brain tumor oxygenation. Laboratory investigation. | 2009-08 |
|
| Trans-sodium crocetinate for treating hypoxia/ischemia. | 2008-06 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:16:22 GMT 2025
by
admin
on
Mon Mar 31 22:16:22 GMT 2025
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| Record UNII |
YP57637WMX
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
378312
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FDA ORPHAN DRUG |
345911
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NCI_THESAURUS |
C68303
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| Code System | Code | Type | Description | ||
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CHEMBL464792
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YP57637WMX
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C82695
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DBSALT002610
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591230-99-8
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10287099
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300000021773
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AB-53
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PRIMARY |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |