MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 585000 | Name: PC-190723

Description:

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

PC-190723 is an antibacterial inhibitor of FtsZ with potent and selective anti-staphylococcal activity including methicillin- and multi-drug-resistant Staphylococcus aureus.

Chemical Structure

PC-190723
PC-190723
CAS#951120-33-5

Theoretical Analysis

MedKoo Cat#: 585000

Name: PC-190723

CAS#: 951120-33-5

Chemical Formula: C14H8ClF2N3O2S

Exact Mass: 354.9994

Molecular Weight: 355.74

Elemental Analysis: C, 47.27; H, 2.27; Cl, 9.97; F, 10.68; N, 11.81; O, 8.99; S, 9.01

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
PC-190723; PC190723; PC 190723
IUPAC/Chemical Name
Benzamide, 3-((6-chlorothiazolo(5,4-b)pyridin-2-yl)methoxy)-2,6-difluoro-
InChi Key
INYJNSBDHOVLAH-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H8ClF2N3O2S/c15-6-3-8-14(19-4-6)23-10(20-8)5-22-9-2-1-7(16)11(12(9)17)13(18)21/h1-4H,5H2,(H2,18,21)
SMILES Code
O=C(N)C1=C(F)C=CC(OCC2=NC3=CC(Cl)=CN=C3S2)=C1F
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 355.74 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.

Recalculate based on batch purity %
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: Kaul M, Mark L, Zhang Y, Parhi AK, LaVoie EJ, Pilch DS. Pharmacokinetics and in vivo antistaphylococcal efficacy of TXY541, a 1-methylpiperidine-4-carboxamide prodrug of PC190723. Biochem Pharmacol. 2013 Dec 15;86(12):1699-707. doi: 10.1016/j.bcp.2013.10.010. Epub 2013 Oct 20. PubMed PMID: 24148278. 2: Tan CM, Therien AG, Lu J, Lee SH, Caron A, Gill CJ, Lebeau-Jacob C, Benton-Perdomo L, Monteiro JM, Pereira PM, Elsen NL, Wu J, Deschamps K, Petcu M, Wong S, Daigneault E, Kramer S, Liang L, Maxwell E, Claveau D, Vaillancourt J, Skorey K, Tam J, Wang H, Meredith TC, Sillaots S, Wang-Jarantow L, Ramtohul Y, Langlois E, Landry F, Reid JC, Parthasarathy G, Sharma S, Baryshnikova A, Lumb KJ, Pinho MG, Soisson SM, Roemer T. Restoring methicillin-resistant Staphylococcus aureus susceptibility to β-lactam antibiotics. Sci Transl Med. 2012 Mar 21;4(126):126ra35. doi: 10.1126/scitranslmed.3003592. PubMed PMID: 22440737. 3: Chen X, Zhang B, Xiao J, Ju F, Li S, Ren C, An L, Chen T, Liu G, Facey P, Mullins JG, Dyson P. RfiA, a novel PAP2 domain-containing polytopic membrane protein that confers resistance to the FtsZ inhibitor PC190723. Future Microbiol. 2015;10(3):325-35. doi: 10.2217/fmb.14.131. PubMed PMID: 25812456. 4: Elsen NL, Lu J, Parthasarathy G, Reid JC, Sharma S, Soisson SM, Lumb KJ. Mechanism of action of the cell-division inhibitor PC190723: modulation of FtsZ assembly cooperativity. J Am Chem Soc. 2012 Aug 1;134(30):12342-5. doi: 10.1021/ja303564a. Epub 2012 Jul 20. PubMed PMID: 22793495. 5: Andreu JM, Schaffner-Barbero C, Huecas S, Alonso D, Lopez-Rodriguez ML, Ruiz-Avila LB, Núñez-Ramírez R, Llorca O, Martín-Galiano AJ. The antibacterial cell division inhibitor PC190723 is an FtsZ polymer-stabilizing agent that induces filament assembly and condensation. J Biol Chem. 2010 May 7;285(19):14239-46. doi: 10.1074/jbc.M109.094722. Epub 2010 Mar 8. PubMed PMID: 20212044; PubMed Central PMCID: PMC2863232. 6: Kaul M, Zhang Y, Parhi AK, Lavoie EJ, Tuske S, Arnold E, Kerrigan JE, Pilch DS. Enterococcal and streptococcal resistance to PC190723 and related compounds: molecular insights from a FtsZ mutational analysis. Biochimie. 2013 Oct;95(10):1880-7. doi: 10.1016/j.biochi.2013.06.010. Epub 2013 Jun 25. PubMed PMID: 23806423; PubMed Central PMCID: PMC5508555. 7: Miguel A, Hsin J, Liu T, Tang G, Altman RB, Huang KC. Variations in the binding pocket of an inhibitor of the bacterial division protein FtsZ across genotypes and species. PLoS Comput Biol. 2015 Mar 26;11(3):e1004117. doi: 10.1371/journal.pcbi.1004117. eCollection 2015 Mar. PubMed PMID: 25811761; PubMed Central PMCID: PMC4374959. 8: Kaul M, Mark L, Zhang Y, Parhi AK, Lavoie EJ, Pilch DS. An FtsZ-targeting prodrug with oral antistaphylococcal efficacy in vivo. Antimicrob Agents Chemother. 2013 Dec;57(12):5860-9. doi: 10.1128/AAC.01016-13. Epub 2013 Sep 16. PubMed PMID: 24041882; PubMed Central PMCID: PMC3837898. 9: Sorto NA, Olmstead MM, Shaw JT. Practical synthesis of PC190723, an inhibitor of the bacterial cell division protein FtsZ. J Org Chem. 2010 Nov 19;75(22):7946-9. doi: 10.1021/jo101720y. Epub 2010 Oct 29. PubMed PMID: 21033691; PubMed Central PMCID: PMC3068231. 10: Hu Z, Zhang S, Zhou W, Ma X, Xiang G. Synthesis and antibacterial activity of 3-benzylamide derivatives as FtsZ inhibitors. Bioorg Med Chem Lett. 2017 Apr 15;27(8):1854-1858. doi: 10.1016/j.bmcl.2017.02.032. Epub 2017 Feb 17. PubMed PMID: 28285910. 11: Haydon DJ, Stokes NR, Ure R, Galbraith G, Bennett JM, Brown DR, Baker PJ, Barynin VV, Rice DW, Sedelnikova SE, Heal JR, Sheridan JM, Aiwale ST, Chauhan PK, Srivastava A, Taneja A, Collins I, Errington J, Czaplewski LG. An inhibitor of FtsZ with potent and selective anti-staphylococcal activity. Science. 2008 Sep 19;321(5896):1673-5. doi: 10.1126/science.1159961. PubMed PMID: 18801997. 12: Adams DW, Wu LJ, Errington J. A benzamide-dependent ftsZ mutant reveals residues crucial for Z-ring assembly. Mol Microbiol. 2016 Mar;99(6):1028-42. doi: 10.1111/mmi.13286. Epub 2015 Dec 22. PubMed PMID: 26601800; PubMed Central PMCID: PMC4832351. 13: Artola M, Ruíz-Avila LB, Ramírez-Aportela E, Martínez RF, Araujo-Bazán L, Vázquez-Villa H, Martín-Fontecha M, Oliva MA, Martín-Galiano AJ, Chacón P, López-Rodríguez ML, Andreu JM, Huecas S. The structural assembly switch of cell division protein FtsZ probed with fluorescent allosteric inhibitors. Chem Sci. 2017 Feb 1;8(2):1525-1534. doi: 10.1039/c6sc03792e. Epub 2016 Oct 21. PubMed PMID: 28616148; PubMed Central PMCID: PMC5460597. 14: Kaul M, Mark L, Zhang Y, Parhi AK, Lyu YL, Pawlak J, Saravolatz S, Saravolatz LD, Weinstein MP, LaVoie EJ, Pilch DS. TXA709, an FtsZ-Targeting Benzamide Prodrug with Improved Pharmacokinetics and Enhanced In Vivo Efficacy against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2015 Aug;59(8):4845-55. doi: 10.1128/AAC.00708-15. Epub 2015 Jun 1. PubMed PMID: 26033735; PubMed Central PMCID: PMC4505295. 15: Weihs F, Wacnik K, Turner RD, Culley S, Henriques R, Foster SJ. Heterogeneous localisation of membrane proteins in Staphylococcus aureus. Sci Rep. 2018 Feb 26;8(1):3657. doi: 10.1038/s41598-018-21750-x. PubMed PMID: 29483609; PubMed Central PMCID: PMC5826919. 16: Monteiro JM, Pereira AR, Reichmann NT, Saraiva BM, Fernandes PB, Veiga H, Tavares AC, Santos M, Ferreira MT, Macário V, VanNieuwenhze MS, Filipe SR, Pinho MG. Peptidoglycan synthesis drives an FtsZ-treadmilling-independent step of cytokinesis. Nature. 2018 Feb 22;554(7693):528-532. doi: 10.1038/nature25506. Epub 2018 Feb 14. PubMed PMID: 29443967; PubMed Central PMCID: PMC5823765. 17: Chiodini G, Pallavicini M, Zanotto C, Bissa M, Radaelli A, Straniero V, Bolchi C, Fumagalli L, Ruggeri P, De Giuli Morghen C, Valoti E. Benzodioxane-benzamides as new bacterial cell division inhibitors. Eur J Med Chem. 2015 Jan 7;89:252-65. doi: 10.1016/j.ejmech.2014.09.100. Epub 2014 Oct 18. PubMed PMID: 25462242. 18: Kaul M, Zhang Y, Parhi AK, Lavoie EJ, Pilch DS. Inhibition of RND-type efflux pumps confers the FtsZ-directed prodrug TXY436 with activity against Gram-negative bacteria. Biochem Pharmacol. 2014 Jun 1;89(3):321-8. doi: 10.1016/j.bcp.2014.03.002. Epub 2014 Mar 14. PubMed PMID: 24637241. 19: Matsui T, Lallo S, Nisa K, Morita H. Filamenting temperature-sensitive mutant Z inhibitors from Glycyrrhiza glabra and their inhibitory mode of action. Bioorg Med Chem Lett. 2017 Mar 15;27(6):1420-1424. doi: 10.1016/j.bmcl.2017.01.095. Epub 2017 Feb 3. PubMed PMID: 28196701. 20: Stokes NR, Baker N, Bennett JM, Berry J, Collins I, Czaplewski LG, Logan A, Macdonald R, Macleod L, Peasley H, Mitchell JP, Nayal N, Yadav A, Srivastava A, Haydon DJ. An improved small-molecule inhibitor of FtsZ with superior in vitro potency, drug-like properties, and in vivo efficacy. Antimicrob Agents Chemother. 2013 Jan;57(1):317-25. doi: 10.1128/AAC.01580-12. Epub 2012 Oct 31. PubMed PMID: 23114779; PubMed Central PMCID: PMC3535900.