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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H22O35S8
Molecular Weight 982.802
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCROSOFATE

SMILES

OS(=O)(=O)OC[C@H]1O[C@@](COS(O)(=O)=O)(O[C@H]2O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]2OS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@@H]1OS(O)(=O)=O

InChI

InChIKey=WEPNHBQBLCNOBB-UGDNZRGBSA-N
InChI=1S/C12H22O35S8/c13-48(14,15)37-1-4-6(43-51(22,23)24)8(45-53(28,29)30)9(46-54(31,32)33)11(40-4)42-12(3-39-50(19,20)21)10(47-55(34,35)36)7(44-52(25,26)27)5(41-12)2-38-49(16,17)18/h4-11H,1-3H2,(H,13,14,15)(H,16,17,18)(H,19,20,21)(H,22,23,24)(H,25,26,27)(H,28,29,30)(H,31,32,33)(H,34,35,36)/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1

HIDE SMILES / InChI

Description

Sucrosofate (sucrose octasulfate) is a class of organic compounds known as disaccharide sulfates carrying one or more sulfate group on a sugar unit. It is used to encapsulate some anticancer drugs in liposomes allowing for highly active formulations against solid tumors and immunotargeting to cancer-overexpressing cell surface receptors. ONIVYDE (liposomal irinotecan) for intravenous use encapsulates an aqueous space containing irinotecan in a gelated or precipitated state as the sucrose octasulfate salt was initially approved by FDA in 1996 for treatment of pancreatic cancer. Sucrose octasulfate (SOS), a chemical analogue of heparin, has been demonstrated to activate fibroblast growth factors signalling pathways and SOS-mediated dimerization of FGF1 was observed. SOS can suppress thrombin generation in plasma that suggests a potential for oversulfated disaccharides in controlling heparin cofactor II -regulated thrombin generation.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ONIVYDE
PubMed

PubMed

TitleDatePubMed
Structure and stability of an acidic fibroblast growth factor from Notophthalmus viridescens.
2002 Nov 29
Binding of sucrose octasulphate to the C-type lectin-like domain of the recombinant natural killer cell receptor NKR-P1A observed by NMR spectroscopy.
2002 Nov 4
Proteinases of common pathogenic bacteria degrade and inactivate the antibacterial peptide LL-37.
2002 Oct
Science review: The use of proton pump inhibitors for gastric acid suppression in critical illness.
2005 Feb
Therapeutic paint of cidofovir/sucralfate gel combination topically administered by spraying for treatment of orf virus infections.
2009 Jun
Topical use of sucralfate in epithelial wound healing: clinical evidences and molecular mechanisms of action.
2010 Jan
Development of a highly stable and targetable nanoliposomal formulation of topotecan.
2010 Jan 4
Patents

Sample Use Guides

In Vivo Use Guide
Recommended dose of ONIVYDE is 70 mg/m^2 intravenous infusion over 90 minutes every two weeks. Recommended starting dose of ONIVYDE in patients homozygous for UGT1A1*28 is 50 mg/m^2 every two weeks.There is no recommended dose of ONIVYDE for patients with serum bilirubin above the upper limit of normal.
Route of Administration: Intravenous
Name Type Language
SUCROSOFATE
INN  
INN  
Official Name English
SUCROSOFATE [INN]
Common Name English
AGENTM-01 FREE ACID
Code English
.ALPHA.-D-GLUCOPYRANOSIDE, 1,3,4,6-TETRA-O-SULFO-.BETA.-D-FRUCTOFURANOSYL, 2,3,4,6-TETRAKIS(HYDROGEN SULFATE)
Common Name English
SUCROSE OCTASULFATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C802
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
Code System Code Type Description
EVMPD
SUB10667MIG
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
PRIMARY
ChEMBL
CHEMBL1235872
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
PRIMARY
INN
6618
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
PRIMARY
MESH
C053081
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
PRIMARY
NCI_THESAURUS
C152444
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
PRIMARY
PUBCHEM
444237
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
PRIMARY
CAS
57680-56-5
Created by admin on Tue Oct 22 05:29:08 UTC 2019 , Edited by admin on Tue Oct 22 05:29:08 UTC 2019
PRIMARY