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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H10O12P2.3Na.H.8H2O
Molecular Weight 550.1834
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOSFRUCTOSE TRISODIUM

SMILES

[H+].O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H](O)C(=O)COP([O-])([O-])=O

InChI

InChIKey=BUMXRRGJJDMPRT-PESUWTOCSA-K
InChI=1S/C6H14O12P2.3Na.8H2O/c7-3(1-17-19(11,12)13)5(9)6(10)4(8)2-18-20(14,15)16;;;;;;;;;;;/h3,5-7,9-10H,1-2H2,(H2,11,12,13)(H2,14,15,16);;;;8*1H2/q;3*+1;;;;;;;;/p-3/t3-,5-,6-;;;;;;;;;;;/m1.........../s1

HIDE SMILES / InChI

Molecular Formula C6H10O12P2.3Na.H.8H2O
Molecular Weight 550.1834
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C6H14O12P2
Molecular Weight 340.1157
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8032987 | https://www.ncbi.nlm.nih.gov/pubmed/17947933 | https://www.ncbi.nlm.nih.gov/pubmed/14693576 | https://www.ncbi.nlm.nih.gov/pubmed/2172175 | https://www.ncbi.nlm.nih.gov/pubmed/19049602

Fosfructose is a cytoprotective natural sugar phosphate under development by Questcor (formerly Cypros) for the potential treatment of cardiovascular ischemia, sickle cell anemia and asthma. Fosfructose acts by stimulating anaerobic glycolysis which generates adenosine triphosphate under ischemic conditions and improve the cellular energy metabolism in ischemic and hypoperfused tissues. Hypoxia forces ischemic tissue to anaerobic glycolysis for energy, which yields two molecules of ATP per glucose in contrast to 36 molecules of ATP generated during oxidative phosphorylation . Addition of exogenous Fosfructose can produce two more molecules of ATP in an uncompensated anaerobic environment and hence facilitate the recovery of ischemia tissue. Fosfructose breaks down into glyceraldehyde-3-phosphate and dihydroxyacetone phosphate, which will further break down into two molecules of pyruvate and finally produce two molecules of ATP. Other mechanisms include inhibition of the generation of oxygen free radicals by neutrophils, stabilization of cell membranes, and maintainance of the correct xanthine dehydrogenase/oxidase ratio by preventing the depletion of phosphorylated compounds in ischemic tissues. In myocardial infarction patients, FDP can improve the hemodynamic parameters, attenuate ECG proven ischemic injury and arrhythmia, prevent ATP and creatine phosphate depletion from ischemic myocardium, reduce infarct size, and increase survival rate. Exogenously administered Fosfructose has also been proven beneficial for a variety of other ischemic organs, such as liver, kidney, bowel and even brain as a consequence of its ability to penetrate to the blood brain barrier. Fosfructose trisodium had been in phase I clinical trials for the treatment of heart transplant rejection. Fosfructose trisodium had been in phase II clinical trials for the treatment of heart failure, perioperativ eischaemia and reperfusion injury. Fosfructose trisodium had been in phase III clinical trials for the treatment of sickle cell anaemia. However, all these research has been discontinued. In China, FDP has been approved and marketed as a commercial drug.

Originator

Sources: Biokhimiya (Moscow) (1940), 5, 567-73.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fosfructose (Questcor).
2001 Dec
Patents

Patents

Sample Use Guides

The recommended dose for patients is 1 g, tid
Route of Administration: Oral
800 mkl of PEP (platelet equalized plasma) from healthy or septic rats and 100 mkl of sterile physiologic solution were added in a plastic spectrophotometer cuvette and read in a spectrophotometer (Spectronic, GenesisTM) at 609 nm wave length. After, 100 mkl of adenosine diphosphate 0.2 mM (ADP, Sigma Chemical Co) was added to the cuvette, which was placed in a 37C bath and kept under constant stirring for 5 min. After a 2 min rest, the cuvette was again read at 609 nm, and the aggregation was calculated. To evaluate the effects of fructose-1,6-bisphosphate in vitro, the same test was performed, but instead of the addition of 100 mkl of sterile physiologic solution, 100 mkl of FBP (fructose-1,6-bisphosphate) diluted in sterile physiologic solution at concentrations of 25, 50, 100, 200 and 400 mM were used to obtain a dose-response curve. Note that the final concentrations of FBP in the tests were 2.5, 5, 10, 20 and 40 mM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:25:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:25:37 GMT 2023
Record UNII
463VBZ2YVD
Record Status Validated (UNII)
Record Version
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Name Type Language
FOSFRUCTOSE TRISODIUM
MART.   USAN   WHO-DD  
USAN  
Official Name English
MONOHYDROGEN MONOSODIUM MONO((2R,3R,4R)-2,3,4-TRIHYDROXY-5-OXOHEXANE-1,6-DIYL BIS(PHOSPHATE)) HYDRATE
Systematic Name English
TRISODIUM FRUCTOSE 1,6-DIPHOSPHATE OCTAHYDRATE
Common Name English
Fosfructose trisodium [WHO-DD]
Common Name English
D-FRUCTOSE, 1,6-BIS(DIHYDROGEN PHOSPHATE), SODIUM SALT, HYDRATE (1:3:8)
Systematic Name English
CPC-111
Code English
FOSFRUCTOSE TRISODIUM [MART.]
Common Name English
FOSFRUCTOSE TRISODIUM [USAN]
Common Name English
D-FRUCTOSE 1,6-BIS(DIHYDROGEN PHOSPHATE), TRISODIUM SALT, OCTAHYDRATE
Common Name English
FOSFRUCTOSE TRISODIUM OCTAHYDRATE
Common Name English
Code System Code Type Description
CAS
102416-04-6
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
ALTERNATIVE
CAS
81028-91-3
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
USAN
JJ-98
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL97893
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
EVMPD
SUB75699
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
SMS_ID
300000040281
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
PUBCHEM
76967543
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
NCI_THESAURUS
C166727
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID801001716
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
FDA UNII
463VBZ2YVD
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY