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MedKoo Cat#: 319631 | Name: Posizolid

Description:

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

Posizolid, also known as AZD-5847 and AZD-2563, is an oxazolidinone antibiotic under investigation by AstraZeneca for the treatment of bacterial infections. At a concentration of 2 mg/L it inhibited 98% of all Gram-positive bacteria tested in vitro. The overall MIC90 was 1.0 mg/liter (range, 0.125 to 4 mg/liter). The MICs of AZD5847 for isolates of Mycobacterium tuberculosis were similar among drug-sensitive strains, multidrug-resistant (MDR) strains, and extensively drug resistant (XDR) strains. The good in vitro activity of AZD5847 against M. tuberculosis and the lack of cross-resistance make this agent a promising anti-TB drug candidate.

Chemical Structure

Posizolid
Posizolid
CAS#252260-02-9

Theoretical Analysis

MedKoo Cat#: 319631

Name: Posizolid

CAS#: 252260-02-9

Chemical Formula: C21H21F2N3O7

Exact Mass: 465.1348

Molecular Weight: 465.41

Elemental Analysis: C, 54.20; H, 4.55; F, 8.16; N, 9.03; O, 24.06

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 #
417702-79-5 252260-02-9
Synonym
AZD-5847; AZD5847; AZD 5847; AZD2563; AZD 2563; AZD-2563, Posizolid.
IUPAC/Chemical Name
(5R)-3-[4-[1-[(2S)-2,3-Dihydroxypropanoyl]-3,6-dihydro-2H-pyridin-4-yl]-3,5-difluorophenyl]-5-(1,2-oxazol-3-yloxymethyl)-1,3-oxazolidin-2-one
InChi Key
HBUJYEUPIIJJOS-PBHICJAKSA-N
InChi Code
InChI=1S/C21H21F2N3O7/c22-15-7-13(26-9-14(33-21(26)30)11-31-18-3-6-32-24-18)8-16(23)19(15)12-1-4-25(5-2-12)20(29)17(28)10-27/h1,3,6-8,14,17,27-28H,2,4-5,9-11H2/t14-,17+/m1/s1
SMILES Code
O=C1O[C@@H](COC2=NOC=C2)CN1C3=CC(F)=C(C4=CCN(C([C@@H](O)CO)=O)CC4)C(F)=C3
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, not in water
Shelf Life
>2 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 465.41 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: Jadhavar PS, Vaja MD, Dhameliya TM, Chakraborti AK. Oxazolidinones as Anti-tubercular Agents: Discovery, Development and Future Perspectives. Curr Med Chem. 2015;22(38):4379-97. PubMed PMID: 26549430. 2: Kumar D, Negi B, Rawat DS. The anti-tuberculosis agents under development and the challenges ahead. Future Med Chem. 2015 Oct;7(15):1981-2003. doi: 10.4155/fmc.15.128. Epub 2015 Oct 27. PubMed PMID: 26505682. 3: Tasneen R, Betoudji F, Tyagi S, Li SY, Williams K, Converse PJ, Dartois V, Yang T, Mendel CM, Mdluli KE, Nuermberger EL. Contribution of Oxazolidinones to the Efficacy of Novel Regimens Containing Bedaquiline and Pretomanid in a Mouse Model of Tuberculosis. Antimicrob Agents Chemother. 2015 Oct 26;60(1):270-7. doi: 10.1128/AAC.01691-15. PubMed PMID: 26503656. 4: Coleman MT, Chen RY, Lee M, Lin PL, Dodd LE, Maiello P, Via LE, Kim Y, Marriner G, Dartois V, Scanga C, Janssen C, Wang J, Klein E, Cho SN, Barry CE 3rd, Flynn JL. PET/CT imaging reveals a therapeutic response to oxazolidinones in macaques and humans with tuberculosis. Sci Transl Med. 2014 Dec 3;6(265):265ra167. doi: 10.1126/scitranslmed.3009500. PubMed PMID: 25473035. 5: Olaru ID, von Groote-Bidlingmaier F, Heyckendorf J, Yew WW, Lange C, Chang KC. Novel drugs against tuberculosis: a clinician's perspective. Eur Respir J. 2015 Apr;45(4):1119-31. doi: 10.1183/09031936.00162314. Epub 2014 Nov 27. Review. PubMed PMID: 25431273. 6: Balasubramanian V, Solapure S, Shandil R, Gaonkar S, Mahesh KN, Reddy J, Deshpande A, Bharath S, Kumar N, Wright L, Melnick D, Butler SL. Pharmacokinetic and pharmacodynamic evaluation of AZD5847 in a mouse model of tuberculosis. Antimicrob Agents Chemother. 2014 Jul;58(7):4185-90. doi: 10.1128/AAC.00137-14. Epub 2014 May 12. PubMed PMID: 24820085; PubMed Central PMCID: PMC4068583. 7: Werngren J, Wijkander M, Perskvist N, Balasubramanian V, Sambandamurthy VK, Rodrigues C, Hoffner S. In vitro activity of AZD5847 against geographically diverse clinical isolates of Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2014 Jul;58(7):4222-3. doi: 10.1128/AAC.02718-14. Epub 2014 Apr 28. PubMed PMID: 24777103; PubMed Central PMCID: PMC4068592. 8: Zhang M, Sala C, Dhar N, Vocat A, Sambandamurthy VK, Sharma S, Marriner G, Balasubramanian V, Cole ST. In vitro and in vivo activities of three oxazolidinones against nonreplicating Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2014 Jun;58(6):3217-23. doi: 10.1128/AAC.02410-14. Epub 2014 Mar 24. PubMed PMID: 24663022; PubMed Central PMCID: PMC4068502. 9: Kwon YS, Jeong BH, Koh WJ. Tuberculosis: clinical trials and new drug regimens. Curr Opin Pulm Med. 2014 May;20(3):280-6. doi: 10.1097/MCP.0000000000000045. Review. PubMed PMID: 24614239. 10: Balasubramanian V, Solapure S, Iyer H, Ghosh A, Sharma S, Kaur P, Deepthi R, Subbulakshmi V, Ramya V, Ramachandran V, Balganesh M, Wright L, Melnick D, Butler SL, Sambandamurthy VK. Bactericidal activity and mechanism of action of AZD5847, a novel oxazolidinone for treatment of tuberculosis. Antimicrob Agents Chemother. 2014;58(1):495-502. doi: 10.1128/AAC.01903-13. Epub 2013 Nov 4. PubMed PMID: 24189255; PubMed Central PMCID: PMC3910779. 11: Cheepsattayakorn A, Cheepsattayakorn R. Novel compounds and drugs and recent patents in treating multidrug-resistant and extensively drug-resistant tuberculosis. Recent Pat Antiinfect Drug Discov. 2012 Aug;7(2):141-56. Review. PubMed PMID: 22670838. 12: Villemagne B, Crauste C, Flipo M, Baulard AR, Déprez B, Willand N. Tuberculosis: the drug development pipeline at a glance. Eur J Med Chem. 2012 May;51:1-16. doi: 10.1016/j.ejmech.2012.02.033. Epub 2012 Feb 25. Review. PubMed PMID: 22421275. 13: Sutcliffe JA. Antibiotics in development targeting protein synthesis. Ann N Y Acad Sci. 2011 Dec;1241:122-52. doi: 10.1111/j.1749-6632.2011.06323.x. Review. PubMed PMID: 22191530. 14: Shaw KJ, Barbachyn MR. The oxazolidinones: past, present, and future. Ann N Y Acad Sci. 2011 Dec;1241:48-70. doi: 10.1111/j.1749-6632.2011.06330.x. Review. PubMed PMID: 22191526. 15: Ginsberg AM. Drugs in development for tuberculosis. Drugs. 2010 Dec 3;70(17):2201-14. doi: 10.2165/11538170-000000000-00000. Review. PubMed PMID: 21080738. 16: Lalloo UG, Ambaram A. New antituberculous drugs in development. Curr HIV/AIDS Rep. 2010 Aug;7(3):143-51. doi: 10.1007/s11904-010-0054-4. Review. PubMed PMID: 20559756. 17: Wookey A, Turner PJ, Greenhalgh JM, Eastwood M, Clarke J, Sefton C. AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro. Clin Microbiol Infect. 2004 Mar;10(3):247-54. PubMed PMID: 15008947. 18: Stockdale MW, Tysall L, Johnson AP, Livermore DM, Woodford N. Low in vitro selection frequencies of enterococcal and staphylococcal mutants resistant to the oxazolidinone AZD2563. Int J Antimicrob Agents. 2004 Jan;23(1):88-91. PubMed PMID: 14732320. 19: Anderegg TR, Jones RN. Preliminary susceptibility testing guidelines for AZD2563, a long-acting oxazolidinone. Int J Antimicrob Agents. 2004 Jan;23(1):6-10. PubMed PMID: 14732307. 20: Gravestock MB, Acton DG, Betts MJ, Dennis M, Hatter G, McGregor A, Swain ML, Wilson RG, Woods L, Wookey A. New classes of antibacterial oxazolidinones with C-5, methylene O-linked heterocyclic side chains. Bioorg Med Chem Lett. 2003 Dec 1;13(23):4179-86. PubMed PMID: 14622997.