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	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8.2304637E11

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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:32:40 UTC 2023` Edited by `admin` on `Fri Dec 15 20:32:40 UTC 2023`
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