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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H14O35S8.8H4N
Molecular Weight 1119.046
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCROSOFATE AMMONIUM

SMILES

[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[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=LQOAWDYRUPQHRM-QRDGSJRXSA-N
InChI=1S/C12H22O35S8.8H3N/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);8*1H3/t4-,5-,6-,7-,8+,9-,10+,11-,12+;;;;;;;;/m1......../s1

HIDE SMILES / InChI
Molecular Formula H3N
Molecular Weight 17.0305
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
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

Merrimack Pharmaceuticals
5
Curator's Comment: Liposomal irinotecan - irinotecan sucrose octasulfate salt liposome injection

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

PubMed

TitleDatePubMed
Structure and stability of an acidic fibroblast growth factor from Notophthalmus viridescens.
2002 Nov 29
Science review: The use of proton pump inhibitors for gastric acid suppression in critical illness.
2005 Feb
Topical use of sucralfate in epithelial wound healing: clinical evidences and molecular mechanisms of action.
2010 Jan
Development of a highly stable and targetable nanoliposomal formulation of topotecan.
2010 Jan 4
Patents

Patents

JP2001352976A
5
JP2011512215A
5
JPH08104617A
5
JPS58208294A
5

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:33:30 UTC 2023
Edited
by admin
on Fri Dec 15 15:33:30 UTC 2023
Record UNII
0M75U2ZH0A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUCROSOFATE AMMONIUM
Common Name English
.ALPHA.-D-GLUCOPYRANOSIDE, 1,3,4,6-TETRA-O-SULFO-.BETA.-D-FRUCTOFURANOSYL, TETRAKIS(HYDROGEN SULFATE), AMMONIUM SALT
Common Name English
.ALPHA.-D-GLUCOPYRANOSIDE, 1,3,4,6-TETRA-O-SULFO-.BETA.-D-FRUCTOFURANOSYL, TETRAKIS(HYDROGEN SULFATE), OCTAAMMONIUM SALT
Common Name English
Code System Code Type Description
PUBCHEM
18643587
Created by admin on Fri Dec 15 15:33:30 UTC 2023 , Edited by admin on Fri Dec 15 15:33:30 UTC 2023
PRIMARY
CAS
74135-13-0
Created by admin on Fri Dec 15 15:33:30 UTC 2023 , Edited by admin on Fri Dec 15 15:33:30 UTC 2023
PRIMARY
CAS
131587-92-3
Created by admin on Fri Dec 15 15:33:30 UTC 2023 , Edited by admin on Fri Dec 15 15:33:30 UTC 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
0M75U2ZH0A
Created by admin on Fri Dec 15 15:33:30 UTC 2023 , Edited by admin on Fri Dec 15 15:33:30 UTC 2023
PRIMARY
Related Record Type Details
Structure of SUCROSOFATE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of SUCROSOFATE
ACTIVE MOIETY
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