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MedKoo Cat#: 571159 | Name: Tosufloxacin

Description:

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

Tosufloxacin, also known as T-3262, is a fluoroquinolone antibiotic used to treat susceptible infections. It has a controversial safety profile in relation to other fluoroquinolones. It is associated with severe thrombocytopenia and nephritis, and hepatotoxicity. It is sold in Japan under the brand name Ozex.

Chemical Structure

Tosufloxacin
Tosufloxacin
CAS#100490-36-6 (free base)

Theoretical Analysis

MedKoo Cat#: 571159

Name: Tosufloxacin

CAS#: 100490-36-6 (free base)

Chemical Formula: C19H15F3N4O3

Exact Mass: 404.1096

Molecular Weight: 404.35

Elemental Analysis: C, 56.44; H, 3.74; F, 14.10; N, 13.86; O, 11.87

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 #
100490-36-6 (free base) 115964-29-9 (tosylate) 104051-69-6 (HCl)
Synonym
Tosufloxacin; A 61827; A-61827; A61827
IUPAC/Chemical Name
1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-7-(3-amino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-
InChi Key
WUWFMDMBOJLQIV-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H15F3N4O3/c20-9-1-2-15(13(21)5-9)26-8-12(19(28)29)16(27)11-6-14(22)18(24-17(11)26)25-4-3-10(23)7-25/h1-2,5-6,8,10H,3-4,7,23H2,(H,28,29)
SMILES Code
O=C(C1=CN(C2=CC=C(F)C=C2F)C3=NC(N4CC(N)CC4)=C(F)C=C3C1=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
>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 404.35 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: Kim YD, Kim MK, Wee WR, Choi HJ. Tosufloxacin deposits in compromised corneas. Optom Vis Sci. 2014 Sep;91(9):e241-4. doi: 10.1097/OPX.0000000000000348. PubMed PMID: 25036547. 2: Kawai Y, Miyashita N, Kubo M, Akaike H, Kato A, Nishizawa Y, Saito A, Kondo E, Teranishi H, Ogita S, Tanaka T, Kawasaki K, Nakano T, Terada K, Ouchi K. Therapeutic efficacy of macrolides, minocycline, and tosufloxacin against macrolide-resistant Mycoplasma pneumoniae pneumonia in pediatric patients. Antimicrob Agents Chemother. 2013 May;57(5):2252-8. doi: 10.1128/AAC.00048-13. Epub 2013 Mar 4. PubMed PMID: 23459497; PubMed Central PMCID: PMC3632908. 3: Niu H, Cui P, Yee R, Shi W, Zhang S, Feng J, Sullivan D, Zhang W, Zhu B, Zhang Y. A Clinical Drug Library Screen Identifies Tosufloxacin as Being Highly Active against Staphylococcus aureus Persisters. Antibiotics (Basel). 2015 Jul 31;4(3):329-36. doi: 10.3390/antibiotics4030329. PubMed PMID: 27025627; PubMed Central PMCID: PMC4790289. 4: Matsubara R, Kibe T, Nomura T. Crystalline nephropathy caused by tosufloxacin. Pediatr Int. 2016 Nov;58(11):1219-1221. doi: 10.1111/ped.13116. PubMed PMID: 27882736. 5: Ishiguro N, Koseki N, Kaiho M, Ariga T, Kikuta H, Togashi T, Oba K, Morita K, Nagano N, Nakanishi M, Hara K, Hazama K, Watanabe T, Yamanaka T, Sasaki S, Furuyama H, Shibata M, Shida S, Ishizaka A, Tabata Y, Aoyagi H, Naito H, Yoshioka M, Horino A, Kenri T; Hokkaido Pediatric Respiratory Infection Study Group. Therapeutic efficacy of azithromycin, clarithromycin, minocycline and tosufloxacin against macrolide-resistant and macrolide-sensitive Mycoplasma pneumoniae pneumonia in pediatric patients. PLoS One. 2017 Mar 13;12(3):e0173635. doi: 10.1371/journal.pone.0173635. eCollection 2017. PubMed PMID: 28288170; PubMed Central PMCID: PMC5348022. 6: Deng FY, Huang CX, Liu Y. [Mn2+-cTMAB-sensitized fluorescent microscopic determination of tosufloxacin tosylate based on a self-ordered ring]. Guang Pu Xue Yu Guang Pu Fen Xi. 2014 Feb;34(2):445-9. Chinese. PubMed PMID: 24822418. 7: Shinohara A, Yoshiki Y, Masamoto Y, Hangaishi A, Nannya Y, Kurokawa M. Moxifloxacin is more effective than tosufloxacin in reducing chemotherapy-induced febrile neutropenia in patients with hematological malignancies. Leuk Lymphoma. 2013 Apr;54(4):794-8. doi: 10.3109/10428194.2012.725848. Epub 2013 Jan 2. PubMed PMID: 22978686. 8: Cooper MA, Andrews JM, Wise R. In-vitro activity of tosufloxacin, a new quinolone antibacterial agent. J Antimicrob Chemother. 1992 Jun;29(6):639-47. PubMed PMID: 1506348. 9: Mitsuyama J, Itoh Y, Takahata M, Okamoto S, Yasuda T. In vitro antibacterial activities of tosufloxacin against and uptake of tosufloxacin by outer membrane mutants of Escherichia coli, Proteus mirabilis, and Salmonella typhimurium. Antimicrob Agents Chemother. 1992 Sep;36(9):2030-6. PubMed PMID: 1329639; PubMed Central PMCID: PMC192431. 10: Arguedas AG, Akaniro JC, Stutman HR, Marks MI. In vitro activity of tosufloxacin, a new quinolone, against respiratory pathogens derived from cystic fibrosis sputum. Antimicrob Agents Chemother. 1990 Nov;34(11):2223-7. PubMed PMID: 2073112; PubMed Central PMCID: PMC172026. 11: Sakata H. [Clinical efficacy of tosufloxacin in children with pneumonia due to Mycoplasma pneumoniae]. Jpn J Antibiot. 2012 Jun;65(3):173-9. Japanese. PubMed PMID: 23173293. 12: Fukuda Y, Takahata M, Mitsuyama J. Pharmacodynamic evaluation of tosufloxacin against Streptococcus pneumoniae in an in vitro model simulating serum concentration. J Infect Chemother. 2006 Feb;12(1):1-8. PubMed PMID: 16506083. 13: Chu DT, Lico IM, Swanson RN, Marsh KC, Plattner JJ, Pernet AG. Synthesis and biological properties of A-71497: a prodrug of tosufloxacin. Drugs Exp Clin Res. 1990;16(9):435-43. PubMed PMID: 2100244. 14: Takahata M, Nishino T. Antibacterial activities of tosufloxacin against anaerobic bacteria and the electron micrograph of its bactericidal effects. Chemotherapy. 1997 May-Jun;43(3):153-8. PubMed PMID: 9142454. 15: Higa F, Akamine M, Haranaga S, Tohyama M, Shinzato T, Tateyama M, Koide M, Saito A, Fujita J. In vitro activity of pazufloxacin, tosufloxacin and other quinolones against Legionella species. J Antimicrob Chemother. 2005 Dec;56(6):1053-7. Epub 2005 Oct 31. PubMed PMID: 16260445. 16: Nord CE, Edlund C. Efficacy of tosufloxacin in the treatment of experimentally induced intra-abdominal infections in rats. Drugs Exp Clin Res. 1992;18(3):89-92. PubMed PMID: 1425208. 17: Xia PY, Feng P, Zhong L, Lv XJ, Lei BJ. Accumulation of ofloxacin and tosufloxacin in fluoroquinolone-resistant E coli. Acta Pharmacol Sin. 2001 Mar;22(3):210-4. PubMed PMID: 11742566. 18: Kiyota H, Machida T, Masuda F, Ohishi Y, Onodera S, Suzuki H, Goto H, Kawahara M, Igarashi H, Endou K, et al. [Single-dose treatment of tosufloxacin (TFLX) for acute uncomplicated cystitis]. Kansenshogaku Zasshi. 1992 Apr;66(4):529-35. Japanese. PubMed PMID: 1624848. 19: Barry AL, Jones RN. In-vitro activities of temafloxacin, tosufloxacin (A-61827) and five other fluoroquinolone agents. J Antimicrob Chemother. 1989 Apr;23(4):527-35. PubMed PMID: 2745259. 20: Kimura N, Miyazaki E, Matsuno O, Abe Y, Tsuda T. [Drug-induced pneumonitis with eosinophilic infiltration due to tosufloxacin tosilate]. Nihon Kokyuki Gakkai Zasshi. 1998 Jul;36(7):618-22. Japanese. PubMed PMID: 9805914.