Gepotidacin | CAS#1075236-89-3 | topoisomerase inhibitor

MedKoo Cat#: 319546 | Name: Gepotidacin

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Description:

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

Gepotidacin, also known as GSK-2140944, is a potent Type II DNA topoisomerase inhibitor. Gepotidacin is a novel antibacterial drug candidate. Gepotidacin Demonstrates Absence of Fluoroquinolone-Like Arthropathy in Juvenile Rats. Gepotidacin is efficacious in a nonhuman primate model of pneumonic plague. When tested against Gram-negative (n = 333) and Gram-positive (n = 225) anaerobes by agar dilution, gepotidacin inhibited 90% of isolates at concentrations of 4 and 2 μg/mL, respectively.

Chemical Structure

Gepotidacin

CAS#1075236-89-3 (free base)

Theoretical Analysis

MedKoo Cat#: 319546

Name: Gepotidacin

CAS#: 1075236-89-3 (free base)

Chemical Formula: C24H28N6O3

Exact Mass: 448.2223

Molecular Weight: 448.53

Elemental Analysis: C, 64.27; H, 6.29; N, 18.74; O, 10.70

Price and Availability

Size	Price	Availability
10mg	USD 450.00	2 Weeks
25mg	USD 850.00	2 Weeks
50mg	USD 1,350.00	2 Weeks

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Related CAS #

1075236-89-3 (free base) 1075235-46-9 (HCl) 1624306-20-2 (mesylate hydrate)

Synonym

Gepotidacin; Gepotidacina; Gepotidacine; gepotidacinum; GSK-2140944; GSK2140944; GSK 2140944; GSK-2140944E; GSK2140944E; GSK 2140944E;

IUPAC/Chemical Name

(2R)-2-[(4-{[(3,4-dihydro-2H-pyrano[2,3-c]pyridin- 6-yl)methyl]amino}piperidin-1-yl)methyl]-1,2-dihydro- 3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

InChi Key

PZFAZQUREQIODZ-LJQANCHMSA-N

InChi Code

InChI=1S/C24H28N6O3/c31-22-4-3-20-24-29(22)15-19(30(24)23(32)13-27-20)14-28-7-5-17(6-8-28)25-11-18-10-16-2-1-9-33-21(16)12-26-18/h3-4,10,12-13,17,19,25H,1-2,5-9,11,14-15H2/t19-/m1/s1

SMILES Code

O=C(C=NC(C=C1)=C23)N3[C@H](CN4CCC(NCC(N=C5)=CC6=C5OCCC6)CC4)CN2C1=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 448.53 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: Perry C, Hossain M, Powell M, Raychaudhuri A, Scangarella-Oman N, Tiffany C, Xu S, Dumont E, Janmohamed S. Design of Two Phase III, Randomized, Multicenter Studies Comparing Gepotidacin with Nitrofurantoin for the Treatment of Uncomplicated Urinary Tract Infection in Female Participants. Infect Dis Ther. 2022 Oct 21:1–14. doi: 10.1007/s40121-022-00706-9. Epub ahead of print. PMID: 36271314; PMCID: PMC9589544. 2: Fishman C, Caverly Rae JM, Posobiec LM, Laffan SB, Lerman SA, Pearson N, Janmohamed S, Dumont E, Nunn-Floyd D, Stanislaus DJ. Novel Bacterial Topoisomerase Inhibitor Gepotidacin Demonstrates Absence of Fluoroquinolone-Like Arthropathy in Juvenile Rats. Antimicrob Agents Chemother. 2022 Oct 18:e0048322. doi: 10.1128/aac.00483-22. Epub ahead of print. PMID: 36255258. 3: Tiffany C, Dumont EF, Hossain M, Srinivasan M, Swift B. Pharmacokinetics, safety, and tolerability of gepotidacin administered as single or repeat ascending doses, in healthy adults and elderly subjects. Clin Transl Sci. 2022 Sep;15(9):2251-2264. doi: 10.1111/cts.13359. Epub 2022 Jul 13. PMID: 35769034; PMCID: PMC9468557. 4: Sánchez-Busó L, Cole MJ, Spiteri G, Day M, Jacobsson S, Golparian D, Sajedi N, Yeats CA, Abudahab K, Underwood A, Bluemel B, Aanensen DM, Unemo M; Centre for Genomic Pathogen Surveillance and the Euro-GASP study group. Europe-wide expansion and eradication of multidrug-resistant Neisseria gonorrhoeae lineages: a genomic surveillance study. Lancet Microbe. 2022 Jun;3(6):e452-e463. doi: 10.1016/S2666-5247(22)00044-1. Epub 2022 May 10. PMID: 35659907. 5: Jakielaszek C, Hossain M, Qian L, Fishman C, Widdowson K, Hilliard JJ, Mannino F, Raychaudhuri A, Carniel E, Demons S, Heine HS, Hershfield J, Russo R, Mega WM, Revelli D, O'Dwyer K. Gepotidacin is efficacious in a nonhuman primate model of pneumonic plague. Sci Transl Med. 2022 Jun;14(647):eabg1787. doi: 10.1126/scitranslmed.abg1787. Epub 2022 Jun 1. PMID: 35648812. 6: Singh SB, Tan CM, Kaelin D, Meinke PT, Miesel L, Olsen DB, Fukuda H, Kishii R, Takei M, Ohata K, Takeuchi T, Shibue T, Takano H, Nishimura A, Fukuda Y. Structure activity relationship of N-1 substituted 1,5-naphthyrid-2-one analogs of oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad- spectrum antibacterial agents (Part-9). Bioorg Med Chem Lett. 2022 Nov 1;75:128808. doi: 10.1016/j.bmcl.2022.128808. Epub 2022 May 21. PMID: 35609741. 7: Beuchel A, Robaa D, Negatu DA, Madani A, Alvarez N, Zimmerman MD, Richter A, Mann L, Hoenke S, Csuk R, Dick T, Imming P. Structure-Activity Relationship of Anti-Mycobacterium abscessus Piperidine-4-carboxamides, a New Class of NBTI DNA Gyrase Inhibitors. ACS Med Chem Lett. 2022 Feb 28;13(3):417-427. doi: 10.1021/acsmedchemlett.1c00549. PMID: 35300094; PMCID: PMC8919391. 8: Sanders MI, Ali E, Buer J, Steinmann J, Rath PM, Verhasselt HL, Kirchhoff L. Antibacterial Activity of the Novel Drug Gepotidacin against Stenotrophomonas maltophilia-An In Vitro and In Vivo Study. Antibiotics (Basel). 2022 Feb 1;11(2):192. doi: 10.3390/antibiotics11020192. PMID: 35203795; PMCID: PMC8868531. 9: Scangarella-Oman NE, Hossain M, Hoover JL, Perry CR, Tiffany C, Barth A, Dumont EF. Dose Selection for Phase III Clinical Evaluation of Gepotidacin (GSK2140944) in the Treatment of Uncomplicated Urinary Tract Infections. Antimicrob Agents Chemother. 2022 Mar 15;66(3):e0149221. doi: 10.1128/AAC.01492-21. Epub 2022 Jan 3. PMID: 34978887; PMCID: PMC8923173. 10: Kaur R, Rani P, Atanasov AG, Alzahrani Q, Gupta R, Kapoor B, Gulati M, Chawla P. Discovery and Development of Antibacterial Agents: Fortuitous and Designed. Mini Rev Med Chem. 2022;22(7):984-1029. doi: 10.2174/1570193X19666211221150119. PMID: 34939541. 11: Hackel MA, Karlowsky JA, Canino MA, Sahm DF, Scangarella-Oman NE. In Vitro Activity of Gepotidacin against Gram-Negative and Gram-Positive Anaerobes. Antimicrob Agents Chemother. 2022 Feb 15;66(2):e0216521. doi: 10.1128/aac.02165-21. Epub 2021 Dec 20. PMID: 34930028; PMCID: PMC8846401. 12: Nuzzo A, Van Horn S, Traini C, Perry CR, Dumont EF, Scangarella-Oman NE, Gardiner DF, Brown JR. Correction to: Microbiome recovery in adult females with uncomplicated urinary tract infections in a randomised phase 2A trial of the novel antibiotic gepotidacin (GSK2140944). BMC Microbiol. 2021 Oct 26;21(1):293. doi: 10.1186/s12866-021-02356-2. Erratum for: BMC Microbiol. 2021 Jun 15;21(1):181. PMID: 34702186; PMCID: PMC8549316. 13: Barth A, Hossain M, Brimhall DB, Perry CR, Tiffany CA, Xu S, Dumont EF. Pharmacokinetics of Oral Formulations of Gepotidacin (GSK2140944), a Triazaacenaphthylene Bacterial Type II Topoisomerase Inhibitor, in Healthy Adult and Adolescent Participants. Antimicrob Agents Chemother. 2022 Jan 18;66(1):e0126321. doi: 10.1128/AAC.01263-21. Epub 2021 Oct 11. PMID: 34633853; PMCID: PMC8765319. 14: VanScoy BD, Lakota EA, Conde H, Fikes S, Bhavnani SM, Elefante PB, Scangarella-Oman NE, Ambrose PG. Gepotidacin Pharmacokinetics-Pharmacodynamics against Escherichia coli in the One-Compartment and Hollow-Fiber In Vitro Infection Model Systems. Antimicrob Agents Chemother. 2021 Nov 17;65(12):e0012221. doi: 10.1128/AAC.00122-21. Epub 2021 Sep 20. PMID: 34543096; PMCID: PMC8597728. 15: Scangarella-Oman NE, Dixon P, Koeth LM, DiFranco-Fisher J, Miller LA. Analysis of antimicrobial susceptibility testing methods and variables and in vitro activity of gepotidacin against urogenital Neisseria gonorrhoeae in men. Diagn Microbiol Infect Dis. 2021 Dec;101(4):115484. doi: 10.1016/j.diagmicrobio.2021.115484. Epub 2021 Jul 10. PMID: 34419740. 16: Nguyen D, Shaik JS, Tai G, Tiffany C, Perry C, Dumont E, Gardiner D, Barth A, Singh R, Hossain M. Comparison between physiologically based pharmacokinetic and population pharmacokinetic modelling to select paediatric doses of gepotidacin in plague. Br J Clin Pharmacol. 2022 Feb;88(2):416-428. doi: 10.1111/bcp.14996. Epub 2021 Sep 2. PMID: 34289143; PMCID: PMC9293063. 17: Nuzzo A, Van Horn S, Traini C, Perry CR, Dumont EF, Scangarella-Oman NE, Gardiner DF, Brown JR. Microbiome recovery in adult females with uncomplicated urinary tract infections in a randomised phase 2A trial of the novel antibiotic gepotidacin (GSK140944). BMC Microbiol. 2021 Jun 15;21(1):181. doi: 10.1186/s12866-021-02245-8. Erratum in: BMC Microbiol. 2021 Oct 26;21(1):293. PMID: 34130619; PMCID: PMC8207760. 18: Aitolo GL, Adeyemi OS, Afolabi BL, Owolabi AO. Neisseria gonorrhoeae Antimicrobial Resistance: Past to Present to Future. Curr Microbiol. 2021 Mar;78(3):867-878. doi: 10.1007/s00284-021-02353-8. Epub 2021 Feb 2. PMID: 33528603. 19: Hossain M, Tiffany C, Tao Y, Barth A, Marbury TC, Preston RA, Dumont E. Pharmacokinetics of Gepotidacin in Subjects With Normal Hepatic Function and Hepatic Impairment. Clin Pharmacol Drug Dev. 2021 Jun;10(6):588-597. doi: 10.1002/cpdd.913. Epub 2021 Jan 15. PMID: 33450142; PMCID: PMC8248074. 20: Sellarès-Nadal J, Burgos J, Falcó V, Almirante B. Investigational and Experimental Drugs for Community-Acquired Pneumonia: the Current Evidence. J Exp Pharmacol. 2020 Nov 19;12:529-538. doi: 10.2147/JEP.S259286. PMID: 33239925; PMCID: PMC7682597.