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+
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 for treating hypoxia/ischemia. | 2008 Jun |
|
Effect of trans sodium crocetinate on brain tumor oxygenation. Laboratory investigation. | 2009 Aug |
|
Trans-sodium crocetinate enhancing survival and glioma response on magnetic resonance imaging to radiation and temozolomide. | 2010 Aug |
|
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 Jan 14 |
|
Protection against focal ischemic injury to the brain by trans-sodium crocetinate. Laboratory investigation. | 2010 Oct |
|
Metabolic reflow as a therapy for ischemic brain injury. | 2011 |
|
Trans-sodium crocetinate provides neuroprotection against cerebral ischemia and reperfusion in obese mice. | 2015 Apr |
|
Perihematomal Cellular Injury Is Reduced by Trans-sodium Crocetinate in a Model of Intracerebral Hemorrhage. | 2015 Oct |
|
Trans sodium crocetinate with temozolomide and radiation therapy for glioblastoma multiforme. | 2017 Feb |
|
Trans sodium crocetinate alleviates ischemia/reperfusion-induced myocardial oxidative stress and apoptosis via the SIRT3/FOXO3a/SOD2 signaling pathway. | 2019 Jun |
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Official Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C68303
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C152713
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
CROCETIN
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
504-39-2
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
SUPERSEDED | |||
|
248-708-0
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
9931
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
27876-94-4
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
m3849
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | Merck Index | ||
|
JK-02
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
DTXSID201015585
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
3918
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
407300
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
62767
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
300000027311
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
5281232
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
20TC155L9C
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
DB05974
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY | |||
|
C010561
Created by
admin on Sat Dec 16 16:04:48 GMT 2023 , Edited by admin on Sat Dec 16 16:04:48 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)