U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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 22.9898
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

Targets

Primary TargetPharmacologyConditionPotency
28.0 µM [IC50]
PubMed

PubMed

TitleDatePubMed
Trans-sodium crocetinate for treating hypoxia/ischemia.
2008 Jun
Effect of trans sodium crocetinate on brain tumor oxygenation. Laboratory investigation.
2009 Aug
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
Evaluation of trans sodium crocetinate on safety and exercise performance in patients with peripheral artery disease and intermittent claudication.
2011 Oct
Trans sodium crocetinate: functional neuroimaging studies in a hypoxic brain tumor.
2011 Oct
Trans-sodium crocetinate improves outcomes in rodent models of occlusive and hemorrhagic stroke.
2014 Oct 2
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:43:16 UTC 2023
Edited
by admin
on Sat Dec 16 08:43:16 UTC 2023
Record UNII
YP57637WMX
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
FDA ORPHAN DRUG 345911
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
NCI_THESAURUS C68303
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL464792
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
FDA UNII
YP57637WMX
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
NCI_THESAURUS
C82695
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
DRUG BANK
DBSALT002610
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
CAS
591230-99-8
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
PUBCHEM
10287099
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
SMS_ID
300000021773
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
USAN
AB-53
Created by admin on Sat Dec 16 08:43:16 UTC 2023 , Edited by admin on Sat Dec 16 08:43:16 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY