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

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H14O35S8.8K
Molecular Weight 1287.525
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCROSOFATE POTASSIUM ANHYDROUS

SMILES

[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]S(=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=XISWAUUBQBEDFB-QRDGSJRXSA-F
InChI=1S/C12H22O35S8.8K/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);;;;;;;;/q;8*+1/p-8/t4-,5-,6-,7-,8+,9-,10+,11-,12+;;;;;;;;/m1......../s1

HIDE SMILES / InChI

Molecular Formula C12H14O35S8
Molecular Weight 974.739
Charge -8
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula K
Molecular Weight 39.0983
Charge 1
Count
MOL RATIO 8 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ONIVYDE

PubMed

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
A8CB6ERJ54
Record Status Validated (UNII)
Record Version