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
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 enhancing survival and glioma response on magnetic resonance imaging to radiation and temozolomide.
2010 Aug
Name Type Language
TRANSCROCETIN
INN   WHO-DD  
INN   USAN  
Official Name English
CROCETIN
INCI   MI  
INCI  
Official Name English
8,8-DIAPOCAROTENEDIOIC ACID
Common Name English
TRANSCROCETINATE
Common Name English
Transcrocetin [WHO-DD]
Common Name English
CROCETIN [INCI]
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
CI 75100 [INCI]
Common Name English
TRANSCROCETINIC ACID
Common Name English
CROCETIN [MI]
Common Name English
CI-75100
Code English
TRANSCROCETINATE LIPOSOMAL COMPONENT OF LEAF-4L6715
Common Name 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
CI 75100
INCI  
INCI  
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
NCI_THESAURUS
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
WIKIPEDIA
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
CAS
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
ECHA (EC/EINECS)
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
INN
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
CAS
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
MERCK INDEX
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
USAN
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
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EPA CompTox
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
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CHEBI
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
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NSC
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
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CHEBI
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
SMS_ID
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
PUBCHEM
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
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FDA UNII
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
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DRUG BANK
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
MESH
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