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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
Structure of TRANSCROCETINATE SODIUM

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+;;

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
28.0 µM [IC50]
PubMed

PubMed

TitleDatePubMed
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
Trans sodium crocetinate alleviates ischemia/reperfusion-induced myocardial oxidative stress and apoptosis via the SIRT3/FOXO3a/SOD2 signaling pathway.
2019 Jun
Name Type Language
TRANSCROCETINATE SODIUM
USAN   WHO-DD  
USAN  
Official Name English
TRANSCROCETINATE SODIUM [USAN]
Common Name English
TSC
Code English
Disodium (all-E)-2,6,11,15-tetramethylhexadecahepta-2,4,6,8,10,12,14-enedioate
Systematic Name English
Transcrocetinate sodium [WHO-DD]
Common Name English
TRANS SODIUM CROCETINATE
Common Name English
DISODIUM TRANS-CROCETINATE
Common Name English
2,4,6,8,10,12,14-HEXADECAHEPTAENEDIOIC ACID, 2,6,11,15-TETRAMETHYL-, SODIUM SALT (1:2), (2E,4E,6E,8E,10E,12E,14E)-
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 378312
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
FDA ORPHAN DRUG 345911
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
NCI_THESAURUS C68303
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL464792
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY
FDA UNII
YP57637WMX
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY
NCI_THESAURUS
C82695
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY
DRUG BANK
DBSALT002610
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY
CAS
591230-99-8
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY
PUBCHEM
10287099
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY
SMS_ID
300000021773
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY
USAN
AB-53
Created by admin on Sat Dec 16 08:43:16 GMT 2023 , Edited by admin on Sat Dec 16 08:43:16 GMT 2023
PRIMARY