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

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
Structure of TRANSCROCETIN

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+

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
28.0 µM [IC50]
PubMed

PubMed

TitleDatePubMed
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 Wed Apr 02 07:05:09 GMT 2025
Edited
by admin
on Wed Apr 02 07:05:09 GMT 2025
Record UNII
20TC155L9C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CROCETIN
INCI   MI  
INCI  
Preferred Name English
TRANSCROCETIN
INN   WHO-DD  
INN   USAN  
Official Name English
CI 75100
INCI  
INCI  
Preferred Name English
8,8-DIAPOCAROTENEDIOIC ACID
Common Name English
TRANSCROCETINATE
Common Name English
Transcrocetin [WHO-DD]
Common Name English
transcrocetin [INN]
Common Name English
TRANSCROCETIN [USAN]
Common Name English
LEAF-4L7520
Common Name English
(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-TETRAMETHYL-2,4,6,8,10,12,14-HEXADECAHEPTAENEDIOIC ACID
Systematic Name English
TRANSCROCETINIC ACID
Common Name English
CROCETIN [MI]
Common Name English
CI-75100
Code English
TRANS-CROCETIN
Common Name English
2,4,6,8,10,12,14-HEXADECAHEPTAENEDIOIC ACID, 2,6,11,15-TETRAMETHYL-, (2E,4E,6E,8E,10E,12E,14E)-
Systematic Name English
LEAF-4L6715 COMPONENT TRANSCROCETINATE
Common Name English
NSC-407300
Code English
(ALL-E)-2,6,11,15-TETRAMETHYLHEXADECA-2,4,6,8,10,12,14-HEPTAENEDIOIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C68303
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C152713
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
WIKIPEDIA
CROCETIN
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
CAS
504-39-2
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
SUPERSEDED
ECHA (EC/EINECS)
248-708-0
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
INN
9931
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
CAS
27876-94-4
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
MERCK INDEX
m3849
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY Merck Index
USAN
JK-02
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID201015585
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
CHEBI
3918
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
NSC
407300
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
CHEBI
62767
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
SMS_ID
300000027311
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
PUBCHEM
5281232
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
FDA UNII
20TC155L9C
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
DRUG BANK
DB05974
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
MESH
C010561
Created by admin on Wed Apr 02 07:05:09 GMT 2025 , Edited by admin on Wed Apr 02 07:05:09 GMT 2025
PRIMARY
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