Lanopepden

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MedKoo CAT#: 319548

CAS#: 1152107-25-9 (free base)

Description: Lanopepden, also known as GSK-1322322 or GSK-322, is a potent and selective peptide deformylase inhibitor with good in vitro activity against bacteria associated with community-acquired pneumonia and skin infections. GSK1322322 had bactericidal activity against S. pneumoniae, H. influenzae, S. pyogenes, and S. aureus, demonstrating a ≥ 3-log(10) decrease in the number of CFU/ml at 4× MIC within 24 h in 29 of the 33 strains tested. GSK1322322 represents a valuable alternative therapy for the treatment of infectious diseases caused by drug-resistant pathogens.


Price and Availability

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Pricing updated 2020-08-15. Prices are subject to change without notice.

Lanopepden is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319548
Name: Lanopepden
CAS#: 1152107-25-9 (free base)
Chemical Formula: C22H34FN7O4
Exact Mass: 479.2656
Molecular Weight: 479.56
Elemental Analysis: C, 55.10; H, 7.15; F, 3.96; N, 20.45; O, 13.34


Related CAS #: 1441390-17-5 (mesylate)   1152107-25-9 (free base)   1441390-22-2 (2 mesylate)   1441390-28-8 (camsylate)    

Synonym: GSK-1322322; GSK1322322; GSK 1322322; GSK-1322322B; GSK-322; GSK322; GSK 322; GSK-1322322J; Lanopepden; GSK 1322322B

IUPAC/Chemical Name: N-[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro- 6-[(9aS)-hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]- 2-methylpyrimidin-4-yl}hydrazin-1-yl)-3-oxopropyl]- N-hydroxyformamide

InChi Key: SWHNZGMQMGFQGW-MSOLQXFVSA-N

InChi Code: InChI=1S/C22H34FN7O4/c1-15-24-20(19(23)21(25-15)29-7-6-28-8-9-34-13-18(28)12-29)26-27-22(32)17(11-30(33)14-31)10-16-4-2-3-5-16/h14,16-18,33H,2-13H2,1H3,(H,27,32)(H,24,25,26)/t17-,18+/m1/s1

SMILES Code: O=CN(C[C@@H](CC1CCCC1)C(NNC2=NC(C)=NC(N3C[C@@]4([H])COCCN4CC3)=C2F)=O)O


Technical Data

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


References

1: Merzoug A, Chikhi A, Bensegueni A, Boucherit H, Okay S. Virtual Screening Approach of Bacterial Peptide Deformylase Inhibitors Results in New Antibiotics. Mol Inform. 2018 Mar;37(3). doi: 10.1002/minf.201700087. Epub 2017 Oct 9. PMID: 28991412.

2: Hoover JL, Singley CM, Elefante P, DeMarsh P, Zalacain M, Rittenhouse S. Reducing Antibacterial Development Risk for GSK1322322 by Exploring Potential Human Dose Regimens in Nonclinical Efficacy Studies Using Immunocompetent Rats. Antimicrob Agents Chemother. 2017 Oct 24;61(11):e00959-17. doi: 10.1128/AAC.00959-17. PMID: 28807913; PMCID: PMC5655044.

3: Hoover J, Lewandowski T, Straub RJ, Novick SJ, DeMarsh P, Aubart K, Rittenhouse S, Zalacain M. Pharmacokinetics/Pharmacodynamics of Peptide Deformylase Inhibitor GSK1322322 against Streptococcus pneumoniae, Haemophilus influenzae, and Staphylococcus aureus in Rodent Models of Infection. Antimicrob Agents Chemother. 2015 Oct 19;60(1):180-9. doi: 10.1128/AAC.01842-15. PMID: 26482300; PMCID: PMC4704172.

4: Parr A, Badman G, Bowen CL, Coffin M, Gupta M, Jones L, Kurtinecz M, Naderer O, Travis E, Zhu J, Patel P. Application of a Stable Isotope Approach to Evaluate Impact of Changes in Manufacturing Parameters for an Immediate-Release Tablet. J Clin Pharmacol. 2016 Jul;56(7):801-5. doi: 10.1002/jcph.664. Epub 2016 Jan 8. PMID: 26479497.

5: Peyrusson F, Butler D, Tulkens PM, Van Bambeke F. Cellular pharmacokinetics and intracellular activity of the novel peptide deformylase inhibitor GSK1322322 against Staphylococcus aureus laboratory and clinical strains with various resistance phenotypes: studies with human THP-1 monocytes and J774 murine macrophages. Antimicrob Agents Chemother. 2015 Sep;59(9):5747-60. doi: 10.1128/AAC.00827-15. Epub 2015 Jul 13. PMID: 26169402; PMCID: PMC4538490.

6: Naderer O, Jones LS, Zhu J, Coffin MD, Kurtinecz M, Dumont E. The Effect of Food and Formulation on the Pharmacokinetics, Safety, and Tolerability of GSK1322322 in Healthy Volunteers. Clin Pharmacol Drug Dev. 2015 Jan;4(1):49-55. doi: 10.1002/cpdd.165. Epub 2014 Oct 27. PMID: 26097792; PMCID: PMC4467258.

7: Min S, Ingraham K, Huang J, McCloskey L, Rilling S, Windau A, Pizzollo J, Butler D, Aubart K, Miller LA, Zalacain M, Holmes DJ, O'Dwyer K. Frequency of Spontaneous Resistance to Peptide Deformylase Inhibitor GSK1322322 in Haemophilus influenzae, Staphylococcus aureus, Streptococcus pyogenes, and Streptococcus pneumoniae. Antimicrob Agents Chemother. 2015 Aug;59(8):4644-52. doi: 10.1128/AAC.00484-15. Epub 2015 May 26. PMID: 26014938; PMCID: PMC4505285.

8: Arat S, Spivak A, Van Horn S, Thomas E, Traini C, Sathe G, Livi GP, Ingraham K, Jones L, Aubart K, Holmes DJ, Naderer O, Brown JR. Microbiome changes in healthy volunteers treated with GSK1322322, a novel antibiotic targeting bacterial peptide deformylase. Antimicrob Agents Chemother. 2015 Feb;59(2):1182-92. doi: 10.1128/AAC.04506-14. Epub 2014 Dec 8. PMID: 25487798; PMCID: PMC4335841.

9: Dubois J, Dubois M, Martel JF, Aubart K, Butler D. In vitro and intracellular activities of peptide deformylase inhibitor GSK1322322 against Legionella pneumophila isolates. Antimicrob Agents Chemother. 2015 Jan;59(1):707-10. doi: 10.1128/AAC.04006-14. Epub 2014 Oct 27. PMID: 25348534; PMCID: PMC4291349.

10: Sangshetti JN, Khan FA, Shinde DB. Peptide deformylase: a new target in antibacterial, antimalarial and anticancer drug discovery. Curr Med Chem. 2015;22(2):214-36. doi: 10.2174/0929867321666140826115734. PMID: 25174923.

11: Corey R, Naderer OJ, O'Riordan WD, Dumont E, Jones LS, Kurtinecz M, Zhu JZ. Safety, tolerability, and efficacy of GSK1322322 in the treatment of acute bacterial skin and skin structure infections. Antimicrob Agents Chemother. 2014 Nov;58(11):6518-27. doi: 10.1128/AAC.03360-14. Epub 2014 Aug 18. PMID: 25136015; PMCID: PMC4249383.

12: Mamaril-Fishman D, Zhu J, Lin M, Felgate C, Jones L, Stump P, Pierre E, Bowen C, Naderer O, Dumont E, Patel P, Gorycki PD, Wen B, Chen L, Deng Y. Investigation of metabolism and disposition of GSK1322322, a peptidase deformylase inhibitor, in healthy humans using the entero-test for biliary sampling. Drug Metab Dispos. 2014 Aug;42(8):1314-25. doi: 10.1124/dmd.114.058420. Epub 2014 May 28. PMID: 24872378.

13: Naderer OJ, Rodvold KA, Jones LS, Zhu JZ, Bowen CL, Chen L, Dumont E. Penetration of GSK1322322 into epithelial lining fluid and alveolar macrophages as determined by bronchoalveolar lavage. Antimicrob Agents Chemother. 2014;58(1):419-23. doi: 10.1128/AAC.01836-13. Epub 2013 Nov 4. PMID: 24189245; PMCID: PMC3910803.

14: Butler D, Chen D, O'Dwyer K, Lewandowski T, Aubart K, Zalacain M. Potent sub-MIC effect of GSK1322322 and other peptide deformylase inhibitors on in vitro growth of Staphylococcus aureus. Antimicrob Agents Chemother. 2014;58(1):290-6. doi: 10.1128/AAC.01292-13. Epub 2013 Oct 28. PMID: 24165188; PMCID: PMC3910740.

15: Naderer OJ, Jones LS, Zhu J, Kurtinecz M, Dumont E. Safety, tolerability, and pharmacokinetics of oral and intravenous administration of GSK1322322, a peptide deformylase inhibitor. J Clin Pharmacol. 2013 Nov;53(11):1168-76. doi: 10.1002/jcph.150. Epub 2013 Aug 13. PMID: 23907665.

16: Naderer OJ, Dumont E, Zhu J, Kurtinecz M, Jones LS. Safety, tolerability and pharmacokinetics of repeat dosing of the antibiotic GSK1322322, a peptide deformylase inhibitor: a randomized placebo-controlled study. J Antimicrob Chemother. 2013 Aug;68(8):1901-9. doi: 10.1093/jac/dkt097. Epub 2013 Apr 3. PMID: 23557930.

17: Naderer OJ, Dumont E, Zhu J, Kurtinecz M, Jones LS. Effect of H2 blockade and food on single-dose pharmacokinetics of GSK1322322, a peptide deformylase inhibitor antibacterial. Antimicrob Agents Chemother. 2013 Jun;57(6):2556-61. doi: 10.1128/AAC.02505-12. Epub 2013 Mar 25. PMID: 23529727; PMCID: PMC3716165.

18: O'Dwyer K, Hackel M, Hightower S, Hoban D, Bouchillon S, Qin D, Aubart K, Zalacain M, Butler D. Comparative analysis of the antibacterial activity of a novel peptide deformylase inhibitor, GSK1322322. Antimicrob Agents Chemother. 2013 May;57(5):2333-42. doi: 10.1128/AAC.02566-12. Epub 2013 Mar 11. PMID: 23478958; PMCID: PMC3632952.

19: Naderer OJ, Dumont E, Zhu J, Kurtinecz M, Jones LS. Single-dose safety, tolerability, and pharmacokinetics of the antibiotic GSK1322322, a novel peptide deformylase inhibitor. Antimicrob Agents Chemother. 2013 May;57(5):2005-9. doi: 10.1128/AAC.01779-12. Epub 2013 Feb 12. PMID: 23403431; PMCID: PMC3632897.

20: 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. PMID: 22191530.