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

Molecular Formula	C12H22O35S8
Molecular Weight	982.802
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Condition	Modality	Targets	Highest Phase	Product
Pancreatic Neoplasms 72	Primary		Approved 7777	ONIVYDE

PubMed

Title	Date	PubMed
Structure and stability of an acidic fibroblast growth factor from Notophthalmus viridescens.	2002 Nov 29	12205097
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	12404632
Proteinases of common pathogenic bacteria degrade and inactivate the antibacterial peptide LL-37.	2002 Oct	12366839
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

Substance Class	Chemical Created by `admin` on `Tue Oct 22 05:29:08 UTC 2019` Edited by `admin` on `Tue Oct 22 05:29:08 UTC 2019`
Record UNII	P7V86EYZ5L
Record Status	`Validated (UNII)`
Record Version

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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