Pixatimod sodium | CAS#1144492-69-2 | TLR9 agonist

MedKoo Cat#: 125257 | Name: Pixatimod sodium

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pixatimod, aslo known as PG-545, is a synthetic sugar modified heparan sulfate mimetic and agonist of toll-like receptor 9 (TLR9), with potential immunostimulating, antineoplastic and anti-viral activities. Pixatimod (PG545) Potently Inhibits SARS-CoV-2 by Disrupting the Spike-ACE2 Interaction. Pixatimod blocks a number of pro-cancerous processes including cell proliferation, invasion, metastasis, angiogenesis and epithelial-mesenchymal transition. These activities have translated into potent activity using a range of different mouse cancer models, including approximately 30 xenograft and 20 syngeneic models. Pixatimod has been tested in combination with a number of approved anti-cancer drugs demonstrating its clinical potential, including with gemcitabine, paclitaxel, sorafenib, platinum agents and an anti-PD-1 antibody.

Chemical Structure

Pixatimod sodium

CAS#1144492-69-2 (sodium)

Theoretical Analysis

MedKoo Cat#: 125257

Name: Pixatimod sodium

CAS#: 1144492-69-2 (sodium)

Chemical Formula: C51H75Na13O60S13

Exact Mass: 2361.7900

Molecular Weight: 2363.75

Elemental Analysis: C, 25.91; H, 3.20; Na, 12.64; O, 40.61; S, 17.63

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

1144492-69-2 (sodium) 1144617-49-1 (free acid)

Synonym

PG-545; 99N289ZQ8L; PG 545; CHEMBL2059499; 1144492-69-2; PIXATIMOD SODIUM

IUPAC/Chemical Name

sodium (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)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-4,5-bis(sulfonatooxy)-2-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis(sulfonatooxy)-2-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis(sulfonatooxy)-2-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-6-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(sulfate)

InChi Key

PHIUHBOJEMIHQZ-YAPWIAIGSA-A

InChi Code

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

SMILES Code

CC(CCC[C@@]([C@@]1([H])CC[C@@]2([H])[C@]([C@]3([H])CC[C@]12C)([H])CC[C@@]4([H])C[C@](O[C@@]5([H])[C@@](OS([O-])(=O)=O)([H])[C@](OS([O-])(=O)=O)([H])[C@@](O[C@]6([H])[C@@](OS([O-])(=O)=O)([H])[C@](OS([O-])(=O)=O)([H])[C@@](O[C@]7([H])[C@@](OS([O-])(=O)=O)([H])[C@](OS([O-])(=O)=O)([H])[C@@](O[C@]8([H])[C@@](OS([O-])(=O)=O)([H])[C@](OS([O-])(=O)=O)([H])[C@@](OS([O-])(=O)=O)([H])[C@@](O8)([H])COS([O-])(=O)=O)([H])[C@@](O7)([H])COS([O-])(=O)=O)([H])[C@@](O6)([H])COS([O-])(=O)=O)([H])[C@@](O5)([H])COS([O-])(=O)=O)([H])CC[C@@]43C)([H])C)C.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 2,363.75 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Lemech C, Dredge K, Bampton D, Hammond E, Clouston A, Waterhouse NJ, Stanley AC, Leveque-El Mouttie L, Chojnowski GM, Haydon A, Pavlakis N, Burge M, Brown MP, Goldstein D. Phase Ib open-label, multicenter study of pixatimod, an activator of TLR9, in combination with nivolumab in subjects with microsatellite-stable metastatic colorectal cancer, metastatic pancreatic ductal adenocarcinoma and other solid tumors. J Immunother Cancer. 2023 Jan;11(1):e006136. doi: 10.1136/jitc-2022-006136. PMID: 36634920; PMCID: PMC9843174. 2: Guimond SE, Mycroft-West CJ, Gandhi NS, Tree JA, Le TT, Spalluto CM, Humbert MV, Buttigieg KR, Coombes N, Elmore MJ, Wand M, Nyström K, Said J, Setoh YX, Amarilla AA, Modhiran N, Sng JDJ, Chhabra M, Young PR, Rawle DJ, Lima MA, Yates EA, Karlsson R, Miller RL, Chen YH, Bagdonaite I, Yang Z, Stewart J, Nguyen D, Laidlaw S, Hammond E, Dredge K, Wilkinson TMA, Watterson D, Khromykh AA, Suhrbier A, Carroll MW, Trybala E, Bergström T, Ferro V, Skidmore MA, Turnbull JE. Synthetic Heparan Sulfate Mimetic Pixatimod (PG545) Potently Inhibits SARS- CoV-2 by Disrupting the Spike-ACE2 Interaction. ACS Cent Sci. 2022 May 25;8(5):527-545. doi: 10.1021/acscentsci.1c01293. Epub 2022 Mar 29. PMID: 35647275; PMCID: PMC9136977. 3: Chhabra M, Wilson JC, Wu L, Davies GJ, Gandhi NS, Ferro V. Structural Insights into Pixatimod (PG545) Inhibition of Heparanase, a Key Enzyme in Cancer and Viral Infections. Chemistry. 2022 Feb 19;28(11):e202104222. doi: 10.1002/chem.202104222. Epub 2022 Jan 31. PMID: 34981584; PMCID: PMC9303737. 4: Chhabra M, Wimmer N, He QQ, Ferro V. Development of Improved Synthetic Routes to Pixatimod (PG545), a Sulfated Oligosaccharide-Steroid Conjugate. Bioconjug Chem. 2021 Nov 17;32(11):2420-2431. doi: 10.1021/acs.bioconjchem.1c00453. Epub 2021 Oct 15. PMID: 34652896. 5: Kinaneh S, Khamaysi I, Karram T, Hamoud S. Heparanase as a potential player in SARS-CoV-2 infection and induced coagulopathy. Biosci Rep. 2021 Jul 30;41(7):BSR20210290. doi: 10.1042/BSR20210290. PMID: 34132790; PMCID: PMC8255537. 6: Hammond E, Dredge K. Heparanase Inhibition by Pixatimod (PG545): Basic Aspects and Future Perspectives. Adv Exp Med Biol. 2020;1221:539-565. doi: 10.1007/978-3-030-34521-1_22. PMID: 32274726. 7: Chhabra M, Ferro V. PI-88 and Related Heparan Sulfate Mimetics. Adv Exp Med Biol. 2020;1221:473-491. doi: 10.1007/978-3-030-34521-1_19. PMID: 32274723. 8: Bendersky V, Yang Y, Brennan TV. Immunomodulatory Activities of the Heparan Sulfate Mimetic PG545. Adv Exp Med Biol. 2020;1221:461-470. doi: 10.1007/978-3-030-34521-1_18. PMID: 32274722. 9: Koliesnik IO, Kuipers HF, Medina CO, Zihsler S, Liu D, Van Belleghem JD, Bollyky PL. The Heparan Sulfate Mimetic PG545 Modulates T Cell Responses and Prevents Delayed-Type Hypersensitivity. Front Immunol. 2020 Feb 6;11:132. doi: 10.3389/fimmu.2020.00132. PMID: 32117279; PMCID: PMC7015948. 10: Hammond E, Haynes NM, Cullinane C, Brennan TV, Bampton D, Handley P, Karoli T, Lanksheer F, Lin L, Yang Y, Dredge K. Immunomodulatory activities of pixatimod: emerging nonclinical and clinical data, and its potential utility in combination with PD-1 inhibitors. J Immunother Cancer. 2018 Jun 14;6(1):54. doi: 10.1186/s40425-018-0363-5. PMID: 29898788; PMCID: PMC6000956. 11: Dredge K, Brennan TV, Hammond E, Lickliter JD, Lin L, Bampton D, Handley P, Lankesheer F, Morrish G, Yang Y, Brown MP, Millward M. A Phase I study of the novel immunomodulatory agent PG545 (pixatimod) in subjects with advanced solid tumours. Br J Cancer. 2018 Apr;118(8):1035-1041. doi: 10.1038/s41416-018-0006-0. Epub 2018 Mar 13. PMID: 29531325; PMCID: PMC5931096.