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

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 C51H75O60S13
Molecular Weight 2064.95
Charge -13
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 29 / 29
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
149124
PubMed

PubMed

TitleDatePubMed
Immunomodulatory activities of pixatimod: emerging nonclinical and clinical data, and its potential utility in combination with PD-1 inhibitors.
2018-06-14
A Phase I study of the novel immunomodulatory agent PG545 (pixatimod) in subjects with advanced solid tumours.
2018-04
Prophylactic Antiheparanase Activity by PG545 Is Antiviral In Vitro and Protects against Ross River Virus Disease in Mice.
2018-04
Inhibition of Heparanase in Pediatric Brain Tumor Cells Attenuates their Proliferation, Invasive Capacity, and In Vivo Tumor Growth.
2017-08
Involvement of heparanase in the pathogenesis of acute kidney injury: nephroprotective effect of PG545.
2017-05-23
The Heparanase Inhibitor PG545 Attenuates Colon Cancer Initiation and Growth, Associating with Increased p21 Expression.
2017-03
Heparanase Inhibition Reduces Glucose Levels, Blood Pressure, and Oxidative Stress in Apolipoprotein E Knockout Mice.
2017
The Cholestanol-Conjugated Sulfated Oligosaccharide PG545 Disrupts the Lipid Envelope of Herpes Simplex Virus Particles.
2016-02
Heparanase-neutralizing antibodies attenuate lymphoma tumor growth and metastasis.
2016-01-19
Heparan sulfate mimetic PG545-mediated antilymphoma effects require TLR9-dependent NK cell activation.
2016-01
PG545 enhances anti-cancer activity of chemotherapy in ovarian models and increases surrogate biomarkers such as VEGF in preclinical and clinical plasma samples.
2015-05
The heparan sulfate mimetic PG545 interferes with Wnt/β-catenin signaling and significantly suppresses pancreatic tumorigenesis alone and in combination with gemcitabine.
2015-03-10
PG545, an angiogenesis and heparanase inhibitor, reduces primary tumor growth and metastasis in experimental pancreatic cancer.
2013-07
Discovery of PG545: a highly potent and simultaneous inhibitor of angiogenesis, tumor growth, and metastasis.
2012-04-26
Potent anti-respiratory syncytial virus activity of a cholestanol-sulfated tetrasaccharide conjugate.
2012-01
PG545, a heparan sulfate mimetic, reduces heparanase expression in vivo, blocks spontaneous metastases and enhances overall survival in the 4T1 breast carcinoma model.
2012
PG545, a dual heparanase and angiogenesis inhibitor, induces potent anti-tumour and anti-metastatic efficacy in preclinical models.
2011-02-15

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 Tue Apr 01 16:30:11 GMT 2025
Edited
by admin
on Tue Apr 01 16:30:11 GMT 2025
Record UNII
99N289ZQ8L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIXATIMOD SODIUM
Common Name English
PG 545
Preferred Name English
PG-545
Common Name 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 Tue Apr 01 16:30:11 GMT 2025 , Edited by admin on Tue Apr 01 16:30:11 GMT 2025
PRIMARY
CAS
1144492-69-2
Created by admin on Tue Apr 01 16:30:11 GMT 2025 , Edited by admin on Tue Apr 01 16:30:11 GMT 2025
PRIMARY
PUBCHEM
57412324
Created by admin on Tue Apr 01 16:30:11 GMT 2025 , Edited by admin on Tue Apr 01 16:30:11 GMT 2025
PRIMARY
Related Record Type Details
Structure of PIXATIMOD
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PIXATIMOD
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