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

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14O12P2
Molecular Weight 340.1157
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOSFRUCTOSE

SMILES

O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)C(=O)COP(O)(O)=O

InChI

InChIKey=XPYBSIWDXQFNMH-UYFOZJQFSA-N
InChI=1S/C6H14O12P2/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)/t3-,5-,6-/m1/s1

HIDE SMILES / InChI

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.
Name Type Language
FOSFRUCTOSE
INN   WHO-DD  
INN  
Official Name English
Fosfructose [WHO-DD]
Common Name English
FRUCTOSE-1,6-DIPHOSPHATE [MI]
Common Name English
D-FRUCTOSE, 1,6-BIS(DIHYDROGEN PHOSPHATE)
Common Name English
FRUCTOSE 1,6-BISPHOSPHATE
Common Name English
fosfructose [INN]
Common Name English
FRUCTOSE 1,6-DIPHOSPHATE
Common Name English
FRUCTOSE-1,6-DIPHOSPHATE
MI  
Common Name English
D-FRUCTOSE 1,6-BISPHOSPHATE
Common Name English
HARDEN-YOUNG ESTER
Common Name English
Classification Tree Code System Code
WHO-ATC C01EB07
Created by admin on Fri Dec 15 16:39:50 GMT 2023 , Edited by admin on Fri Dec 15 16:39:50 GMT 2023
WHO-VATC QC01EB07
Created by admin on Fri Dec 15 16:39:50 GMT 2023 , Edited by admin on Fri Dec 15 16:39:50 GMT 2023
FDA ORPHAN DRUG 112398
Created by admin on Fri Dec 15 16:39:50 GMT 2023 , Edited by admin on Fri Dec 15 16:39:50 GMT 2023
Code System Code Type Description
INN
7864
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PRIMARY
MERCK INDEX
m5574
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PRIMARY Merck Index
CAS
488-69-7
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PRIMARY
CAS
717817-28-2
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ALTERNATIVE
CHEBI
49299
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EPA CompTox
DTXSID0048347
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DAILYMED
M7522JYX1H
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WIKIPEDIA
FRUCTOSE 1,6-BISPHOSPHATE
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FDA UNII
M7522JYX1H
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SMS_ID
100000087019
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ChEMBL
CHEMBL97893
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MESH
C029063
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EVMPD
SUB02264MIG
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CHEBI
28013
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PRIMARY
ECHA (EC/EINECS)
207-683-6
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PRIMARY
CHEBI
16905
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PRIMARY
ChEMBL
CHEMBL1089962
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DRUG BANK
DB13863
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NCI_THESAURUS
C174695
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PUBCHEM
84951
Created by admin on Fri Dec 15 16:39:50 GMT 2023 , Edited by admin on Fri Dec 15 16:39:50 GMT 2023
PRIMARY
RXCUI
2119172
Created by admin on Fri Dec 15 16:39:50 GMT 2023 , Edited by admin on Fri Dec 15 16:39:50 GMT 2023
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