pixatimod   Click here for help

GtoPdb Ligand ID: 9870

Synonyms: compound 18 [PMID: 22458531] | PG-545 | PG545
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Pixatimod (PG545) is a heparan sulphate mimetic that acts as an inhibitor of the heparanase enzyme [3-4]. Structurally it is a cholestanol-conjugated sulfated oligosaccharide.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 60
Hydrogen bond donors 13
Rotatable bonds 43
Topological polar surface area 1009.58
Molecular weight 2076.02
XLogP -14.66
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC(CCCC(C1CCC2C1(C)CCC1C2CCC2C1(C)CCC(C2)OC1OC(COS(=O)(=O)O)C(C(C1OS(=O)(=O)O)OS(=O)(=O)O)OC1OC(COS(=O)(=O)O)C(C(C1OS(=O)(=O)O)OS(=O)(=O)O)OC1OC(COS(=O)(=O)O)C(C(C1OS(=O)(=O)O)OS(=O)(=O)O)OC1OC(COS(=O)(=O)O)C(C(C1OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)C)C
Isomeric SMILES CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@H](C2)O[C@@H]1O[C@H](COS(=O)(=O)O)[C@H]([C@@H]([C@H]1OS(=O)(=O)O)OS(=O)(=O)O)O[C@H]1O[C@H](COS(=O)(=O)O)[C@H]([C@@H]([C@H]1OS(=O)(=O)O)OS(=O)(=O)O)O[C@H]1O[C@H](COS(=O)(=O)O)[C@H]([C@@H]([C@H]1OS(=O)(=O)O)OS(=O)(=O)O)O[C@H]1O[C@H](COS(=O)(=O)O)[C@H]([C@@H]([C@H]1OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)C)C
InChI InChI=1S/C51H88O60S13/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)/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
InChI Key LNUFLCYMSVYYNW-ZPJMAFJPSA-N
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Summary of Clinical Use Click here for help
A dose-finding Phase 1 study in 4 subjects, that began in 2010, was terminated due to patients developing unexpected injection site reactions (NCT01252095). However, pixatimod (PG545) has now completed a separate safety and tolerability Phase 1 clinical study (NCT02042781) in patients with advanced solid tumours. Study resuts indicate evidence of immune cell stimulation and a level of disease control in some patients [2]. These results support the proposed mechanism of action of PG545.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01252095 Study of the Safety and Tolerability of PG545 in Patients With Advanced Solid Tumours Phase 1 Interventional Zucero Pty Ltd
NCT02042781 Study of the Safety and Tolerability of IV Infused PG545 in Patients With Advanced Solid Tumours Phase 1 Interventional Zucero Pty Ltd