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Details

Stereochemistry ABSOLUTE
Molecular Formula C51H75O60S13.13Na
Molecular Weight 2363.817
Optical Activity UNSPECIFIED
Defined Stereocenters 29 / 29
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIXATIMOD SODIUM

SMILES

[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]5([H])O[C@H](COS([O-])(=O)=O)[C@@H](O[C@@]6([H])O[C@H](COS([O-])(=O)=O)[C@@H](O[C@@]7([H])O[C@H](COS([O-])(=O)=O)[C@@H](O[C@@]8([H])O[C@H](COS([O-])(=O)=O)[C@@H](OS([O-])(=O)=O)[C@H](OS([O-])(=O)=O)[C@H]8OS([O-])(=O)=O)[C@H](OS([O-])(=O)=O)[C@H]7OS([O-])(=O)=O)[C@H](OS([O-])(=O)=O)[C@H]6OS([O-])(=O)=O)[C@H](OS([O-])(=O)=O)[C@H]5OS([O-])(=O)=O)[C@H](C)CCCC(C)C

InChI

InChIKey=PHIUHBOJEMIHQZ-YAPWIAIGSA-A
InChI=1S/C51H88O60S13.13Na/c1-22(2)7-6-8-23(3)27-11-12-28-26-10-9-24-17-25(13-15-50(24,4)29(26)14-16-51(27,28)5)95-46-42(108-121(79,80)81)38(104-117(67,68)69)34(30(96-46)18-91-112(52,53)54)100-47-43(109-122(82,83)84)39(105-118(70,71)72)35(31(97-47)19-92-113(55,56)57)101-48-44(110-123(85,86)87)40(106-119(73,74)75)36(32(98-48)20-93-114(58,59)60)102-49-45(111-124(88,89)90)41(107-120(76,77)78)37(103-116(64,65)66)33(99-49)21-94-115(61,62)63;;;;;;;;;;;;;/h22-49H,6-21H2,1-5H3,(H,52,53,54)(H,55,56,57)(H,58,59,60)(H,61,62,63)(H,64,65,66)(H,67,68,69)(H,70,71,72)(H,73,74,75)(H,76,77,78)(H,79,80,81)(H,82,83,84)(H,85,86,87)(H,88,89,90);;;;;;;;;;;;;/q;13*+1/p-13/t23-,24+,25+,26+,27-,28+,29+,30-,31-,32-,33-,34-,35-,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,46-,47-,48-,49-,50+,51-;;;;;;;;;;;;;/m1............./s1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C51H75O60S13
Molecular Weight 2064.95
Charge -13
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 29 / 29
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

PG-545 is a heparan sulfate (HS) mimetic that inhibits tumour angiogenesis by sequestering angiogenic growth factors in the extracellular matrix (ECM), thus limiting subsequent binding to receptors. Importantly, PG-545 also inhibits heparanase, the only endoglycosidase which cleaves HS chains in the ECM. The anti- respiratory syncytial virus (RSV) activity of PG-545 was due to both partial inhibition of the virus attachment to cells and a more profound interference with some post-attachment steps as PG-545 efficiently neutralized infectivity of the cell-adsorbed virus. The anti-RSV activity of PG-545 was reduced when tested in the presence of human nasal secretions. Serial passages of RSV in the presence of increasing concentrations of PG-545 selected for weakly resistant viral variants that comprised the F168S and the P180S amino acid substitutions in the viral G protein. PG-545 has an immunomodulatory properties. PG-545 stimulates innate immune responses against tumours in preclinical cancer models. PG-545 is in phase I clinical trial for the treatment of pancreatic cancer.

Originator

Approval Year

Unknown
139594
PubMed

PubMed

TitleDatePubMed
The heparan sulfate mimetic PG545 interferes with Wnt/β-catenin signaling and significantly suppresses pancreatic tumorigenesis alone and in combination with gemcitabine.
2015 Mar 10
PG545 enhances anti-cancer activity of chemotherapy in ovarian models and increases surrogate biomarkers such as VEGF in preclinical and clinical plasma samples.
2015 May
Prophylactic Antiheparanase Activity by PG545 Is Antiviral In Vitro and Protects against Ross River Virus Disease in Mice.
2018 Apr

Sample Use Guides

In Vivo Use Guide
25, 50, 100 and 150 mg once weekly for 28 days
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:31:37 GMT 2023
Edited
by admin
on Sat Dec 16 11:31:37 GMT 2023
Record UNII
99N289ZQ8L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIXATIMOD SODIUM
Common Name English
PG-545
Common Name English
PG 545
Code English
.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,5.ALPHA.)-CHOLESTAN-3-YL O-2,3,4,6-TETRA-O-SULFO-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-2,3,6-TRI-O-SULFO-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-2,3,6-TRI-O-SULFO-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-, 2,3,6-TRIS(HYDROGEN SULFATE), SO
Systematic Name English
((2R,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-(((3S,5S,8R,9S,10S,13R,14S,17R)-17-((1R)-1,5-DIMETHYLHEXYL)-10,13-DIMETHYL-2,3,4,5,6,7,8,9,11,12,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA(A)PHENANTHREN-3-YL)OXY)-4,5-DISULFOO
Systematic Name English
Code System Code Type Description
FDA UNII
99N289ZQ8L
Created by admin on Sat Dec 16 11:31:37 GMT 2023 , Edited by admin on Sat Dec 16 11:31:37 GMT 2023
PRIMARY
CAS
1144492-69-2
Created by admin on Sat Dec 16 11:31:37 GMT 2023 , Edited by admin on Sat Dec 16 11:31:37 GMT 2023
PRIMARY
PUBCHEM
57412324
Created by admin on Sat Dec 16 11:31:37 GMT 2023 , Edited by admin on Sat Dec 16 11:31:37 GMT 2023
PRIMARY
Related Record Type Details
Structure of PIXATIMOD
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PIXATIMOD
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