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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H22O35S8
Molecular Weight 982.8114
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCROSOFATE

SMILES

C([C@]1([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(O1)O[C@@]2(COS(=O)(=O)O)[C@]([H])([C@@]([H])([C@@]([H])(COS(=O)(=O)O)O2)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=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
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

Curator's Comment:: Liposomal irinotecan - irinotecan sucrose octasulfate salt liposome injection

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: ONIVYDE is a sterile, white to slightly yellow opaque isotonic liposomal dispersion. Each 10 mL single-dose vial contains 43 mg irinotecan free base at a concentration of 4.3 mg/mL. The liposome is a unilamellar lipid bilayer vesicle, approximately 110 nm in diameter, which encapsulates an aqueous space containing irinotecan in a gelated or precipitated state as the sucrose octasulfate salt
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
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 Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
Code System Code Type Description
EVMPD
SUB10667MIG
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
DRUG BANK
DB01901
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
ChEMBL
CHEMBL1235872
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
INN
6618
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
MESH
C053081
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
NCI_THESAURUS
C152444
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
FDA UNII
P7V86EYZ5L
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
PUBCHEM
444237
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY
CAS
57680-56-5
Created by admin on Sat Jun 26 01:00:36 UTC 2021 , Edited by admin on Sat Jun 26 01:00:36 UTC 2021
PRIMARY