SUCROSOFATE

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207793lbl.pdf
Curator's Comment: Description was created using several sources including http://www.drugbank.ca/drugs/DB01901; https://www.ncbi.nlm.nih.gov/pubmed/18540049; https://www.ncbi.nlm.nih.gov/pubmed/19686789; https://www.ncbi.nlm.nih.gov/pubmed/20053992

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

Condition	Modality	Targets	Highest Phase	Product
Pancreatic cancer 97 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207793lbl.pdf	Primary		Approved 8429	ONIVYDE Approved Use ONIVYDE is a topoisomerase inhibitor indicated, in combination with fluorouracil and leucovorin, for the treatment of patients with metastatict adenocarcinoma of pancreas after disease progression following gemcitabine-based therapy. Launch Date 1996

PubMed

Title	Date	PubMed
Science review: The use of proton pump inhibitors for gastric acid suppression in critical illness.	2005 Feb	15693983
Therapeutic paint of cidofovir/sucralfate gel combination topically administered by spraying for treatment of orf virus infections.	2009 Jun	19381838
Topical use of sucralfate in epithelial wound healing: clinical evidences and molecular mechanisms of action.	2010 Jan	19832693
Development of a highly stable and targetable nanoliposomal formulation of topotecan.	2010 Jan 4	19686789

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

In Vitro Use Guide

Unknown

Name

Type

Language

SUCROSOFATE

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