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MedKoo Cat#: 597312 | Name: Grepafloxacin, (S)-

Description:

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

Grepafloxacin, (S)- is an oral broad-spectrum fluoroquinolone antibacterial agent used to treat bacterial infections.

Chemical Structure

Grepafloxacin, (S)-
Grepafloxacin, (S)-
CAS#146761-69-5

Theoretical Analysis

MedKoo Cat#: 597312

Name: Grepafloxacin, (S)-

CAS#: 146761-69-5

Chemical Formula: C19H22FN3O3

Exact Mass: 359.1645

Molecular Weight: 359.40

Elemental Analysis: C, 63.50; H, 6.17; F, 5.29; N, 11.69; O, 13.35

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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Synonym
Grepafloxacin, (S)-; Grepafloxacin, (-)-; L-Grepafloxacin;
IUPAC/Chemical Name
(S)-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
InChi Key
AIJTTZAVMXIJGM-JTQLQIEISA-N
InChi Code
InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)/t10-/m0/s1
SMILES Code
O=C(C1=CN(C2CC2)C3=C(C(C)=C(F)C(N4C[C@H](C)NCC4)=C3)C1=O)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
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 359.40 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: Gontijo AV, Brillault J, Grégoire N, Lamarche I, Gobin P, Couet W, Marchand S. Biopharmaceutical characterization of nebulized antimicrobial agents in rats: 1. Ciprofloxacin, moxifloxacin, and grepafloxacin. Antimicrob Agents Chemother. 2014 Jul;58(7):3942-9. doi: 10.1128/AAC.02818-14. Epub 2014 May 5. PubMed PMID: 24798283; PubMed Central PMCID: PMC4068515. 2: Ramos-Payán M, Villar-Navarro M, Fernández-Torres R, Callejón-Mochón M, Bello-López MA. Electromembrane extraction (EME)--an easy, novel and rapid extraction procedure for the HPLC determination of fluoroquinolones in wastewater samples. Anal Bioanal Chem. 2013 Mar;405(8):2575-84. doi: 10.1007/s00216-012-6664-5. Epub 2013 Jan 11. PubMed PMID: 23307130. 3: Hishigaki H, Kuhara S. hERGAPDbase: a database documenting hERG channel inhibitory potentials and APD-prolongation activities of chemical compounds. Database (Oxford). 2011 May 17;2011:bar017. doi: 10.1093/database/bar017. Print 2011. PubMed PMID: 21586548; PubMed Central PMCID: PMC3096323. 4: Green JR, Diaz GJ, Limberis JT, Houseman KA, Su Z, Martin RL, Cox BF, Kantor S, Gintant GA. Ventricular rate adaptation: a novel, rapid, cellular-based in-vitro assay to identify proarrhythmic and torsadogenic compounds. J Pharmacol Toxicol Methods. 2011 Jul-Aug;64(1):68-73. doi: 10.1016/j.vascn.2011.03.005. Epub 2011 Apr 2. PubMed PMID: 21440075. 5: Ramos Payán M, Bello López MÁ, Fernández-Torres R, González JA, Callejón Mochón M. Hollow fiber-based liquid phase microextraction (HF-LPME) as a new approach for the HPLC determination of fluoroquinolones in biological and environmental matrices. J Pharm Biomed Anal. 2011 May 15;55(2):332-41. doi: 10.1016/j.jpba.2011.01.037. Epub 2011 Feb 24. PubMed PMID: 21353435. 6: Kenny DJ, Sefton AM, Brooks TJ, Laws TR, Simpson AJ, Atkins HS. Evaluation of azithromycin, trovafloxacin and grepafloxacin as prophylaxis for experimental murine melioidosis. Int J Antimicrob Agents. 2010 Jul;36(1):87-9. doi: 10.1016/j.ijantimicag.2010.03.019. Epub 2010 May 11. PubMed PMID: 20462743. 7: Atkins HS, Spencer S, Brew SD, Jenner DC, Sefton AM, MacMillan AP, Brooks TJ, Simpson AJ. Evaluation of azithromycin, trovafloxacin and grepafloxacin as prophylaxis against experimental murine Brucella melitensis infection. Int J Antimicrob Agents. 2010 Jul;36(1):66-8. doi: 10.1016/j.ijantimicag.2009.10.003. Epub 2009 Dec 21. PubMed PMID: 20022474. 8: Kenny DJ, Sefton AM, Steward J, Brooks TJ, Simpson AJ, Atkins HS. Efficacy of the quinolones trovafloxacin and grepafloxacin for therapy of experimental tularaemia and plague. Int J Antimicrob Agents. 2009 Nov;34(5):502-3. doi: 10.1016/j.ijantimicag.2009.06.023. Epub 2009 Aug 21. PubMed PMID: 19699615. 9: Alvarez AI, Pérez M, Prieto JG, Molina AJ, Real R, Merino G. Fluoroquinolone efflux mediated by ABC transporters. J Pharm Sci. 2008 Sep;97(9):3483-93. doi: 10.1002/jps.21233. Review. PubMed PMID: 18200507. 10: Ando T, Kusuhara H, Merino G, Alvarez AI, Schinkel AH, Sugiyama Y. Involvement of breast cancer resistance protein (ABCG2) in the biliary excretion mechanism of fluoroquinolones. Drug Metab Dispos. 2007 Oct;35(10):1873-9. Epub 2007 Jul 16. PubMed PMID: 17639028. 11: Balkhy HH, Memish ZA, Shibl A, Elbashier A, Osoba A. In vitro activity of quinolones against S. pneumoniae, H. influenzae and M. catarrhalis in Saudi Arabia. East Mediterr Health J. 2005 Jan-Mar;11(1-2):36-44. PubMed PMID: 16532669. 12: Sasabe H, Kato Y, Suzuki T, Itose M, Miyamoto G, Sugiyama Y. Carrier-mediated uptake of grepafloxacin, a fluoroquinolone antibiotic, by the isolated rat lung cells. Drug Metab Pharmacokinet. 2005 Dec;20(6):491-5. PubMed PMID: 16415534. 13: Rodríguez-Ibáñez M, Sánchez-Castaño G, Montalar-Montero M, Garrigues TM, Bermejo M, Merino V. Mathematical modelling of in situ and in vitro efflux of ciprofloxacin and grepafloxacin. Int J Pharm. 2006 Jan 3;307(1):33-41. Epub 2005 Oct 27. PubMed PMID: 16257153. 14: Firsov AA, Lubenko IY, Vostrov SN, Portnoy YA, Zinner SH. Antistaphylococcal effect related to the area under the curve/MIC ratio in an in vitro dynamic model: predicted breakpoints versus clinically achievable values for seven fluoroquinolones. Antimicrob Agents Chemother. 2005 Jul;49(7):2642-7. PubMed PMID: 15980331; PubMed Central PMCID: PMC1168651. 15: Owens RC Jr, Ambrose PG. Antimicrobial safety: focus on fluoroquinolones. Clin Infect Dis. 2005 Jul 15;41 Suppl 2:S144-57. Review. PubMed PMID: 15942881. 16: Kawamura-Sato K, Hasegawa T, Torii K, Ito H, Ohta M. Prevalence of Ile-460-Val/ParE substitution in clinical Streptococcus pneumoniae isolates that were less susceptible to fluoroquinolones. Curr Microbiol. 2005 Jul;51(1):27-30. Epub 2005 May 31. PubMed PMID: 15942701. 17: Stout JE, Sens K, Mietzner S, Obman A, Yu VL. Comparative activity of quinolones, macrolides and ketolides against Legionella species using in vitro broth dilution and intracellular susceptibility testing. Int J Antimicrob Agents. 2005 Apr;25(4):302-7. PubMed PMID: 15784309. 18: Dupont P, Hocquet D, Jeannot K, Chavanet P, Plésiat P. Bacteriostatic and bactericidal activities of eight fluoroquinolones against MexAB-OprM-overproducing clinical strains of Pseudomonas aeruginosa. J Antimicrob Chemother. 2005 Apr;55(4):518-22. Epub 2005 Feb 18. PubMed PMID: 15722391. 19: Itoh T, Itagaki S, Sumi Y, Hirano T, Takemoto I, Iseki K. Uptake of irinotecan metabolite SN-38 by the human intestinal cell line Caco-2. Cancer Chemother Pharmacol. 2005 May;55(5):420-4. Epub 2004 Nov 23. PubMed PMID: 15565324. 20: Sikri V, Pal D, Jain R, Kalyani D, Mitra AK. Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux. Am J Ther. 2004 Nov-Dec;11(6):433-42. PubMed PMID: 15543082.

View History

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