Synonym
CI 978; CI-978; CI978; Sparfloxacin; Esparfloxacino; Zagam
IUPAC/Chemical Name
5-amino-1-cyclopropyl-7-((3S,5R)-3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
InChi Key
DZZWHBIBMUVIIW-DTORHVGOSA-N
InChi Code
InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+
SMILES Code
O=C(C1=CN(C2CC2)C3=C(C(N)=C(F)C(N4C[C@H](C)N[C@H](C)C4)=C3F)C1=O)O
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
Biological target:
Sparfloxacin shows broad and potent antibacterial activity.
In vitro activity:
Sparfloxacin led to concentration-dependent loss in in human epidermal melanocytes (HEMa-LP) cell viability (EC50 ∼0.25 mM), inhibited tyrosinase activity, and reduced melanin content. Additionally, sparfloxacin depleted antioxidant enzyme activities (SOD, CAT, GPx) in melanocytes. These findings shed light on fluoroquinolones' toxicity mechanisms in pigmented tissues.
Reference: Pharmacol Rep. 2015 Feb;67(1):38-43. https://pubmed.ncbi.nlm.nih.gov/25560573/
In vivo activity:
Sparfloxacin could be a biochemical modulator in treatment of colon cancer with chemotherapeutic drugs. In a model of colon carcinoma C26 in BALB/c mice and human colon carcinoma HCT116 xenografts in nude mice, high expression of HERG protein was detected in colon cancer C26, HCT116 and HT-29 cells. Sparfloxacin inhibited the cell viability of colon cancer cells in a dose-dependent manner. Sparfloxacin induced apoptosis and inhibited migration and invasion of colon cancer HCT116 cells.
Reference: Oncol Rep. 2010 Jun;23(6):1747-56. https://pubmed.ncbi.nlm.nih.gov/20428834/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
3.3 |
8.49 |
|
| Water |
0.7 |
1.71 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
392.41
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.
| 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 |
Formulation protocol:
1. Beberok A, Wrześniok D, Otręba M, Buszman E. Impact of sparfloxacin on melanogenesis and antioxidant defense system in normal human melanocytes HEMa-LP - An in vitro study. Pharmacol Rep. 2015 Feb;67(1):38-43. doi: 10.1016/j.pharep.2014.07.015. Epub 2014 Aug 10. PMID: 25560573.
2. Lourenço MC, Junior IN, De Souza MV. In vitro activity of ciprofloxacin, ofloxacin, levofloxacin, sparfloxacin and gatifloxacin against multidrug-resistant Mycobacterium tuberculosis in Rio de Janeiro Brazil. Med Mal Infect. 2007 May;37(5):295-6. doi: 10.1016/j.medmal.2007.03.011. Epub 2007 Apr 24. PMID: 17459633.
3. Gong JH, Liu XJ, Shang BY, Chen SZ, Zhen YS. HERG K+ channel related chemosensitivity to sparfloxacin in colon cancer cells. Oncol Rep. 2010 Jun;23(6):1747-56. doi: 10.3892/or_00000820. PMID: 20428834.
4. Bharal N, Pillai KK, Vohora D. Effects of sparfloxacin on CNS functions and urinary hydroxyproline in mice. Pharmacol Res. 2006 Aug;54(2):111-7. doi: 10.1016/j.phrs.2006.03.004. Epub 2006 Mar 22. PMID: 16701999.
In vitro protocol:
1. Beberok A, Wrześniok D, Otręba M, Buszman E. Impact of sparfloxacin on melanogenesis and antioxidant defense system in normal human melanocytes HEMa-LP - An in vitro study. Pharmacol Rep. 2015 Feb;67(1):38-43. doi: 10.1016/j.pharep.2014.07.015. Epub 2014 Aug 10. PMID: 25560573.
2. Lourenço MC, Junior IN, De Souza MV. In vitro activity of ciprofloxacin, ofloxacin, levofloxacin, sparfloxacin and gatifloxacin against multidrug-resistant Mycobacterium tuberculosis in Rio de Janeiro Brazil. Med Mal Infect. 2007 May;37(5):295-6. doi: 10.1016/j.medmal.2007.03.011. Epub 2007 Apr 24. PMID: 17459633.
In vivo protocol:
1. Gong JH, Liu XJ, Shang BY, Chen SZ, Zhen YS. HERG K+ channel related chemosensitivity to sparfloxacin in colon cancer cells. Oncol Rep. 2010 Jun;23(6):1747-56. doi: 10.3892/or_00000820. PMID: 20428834.
2. Bharal N, Pillai KK, Vohora D. Effects of sparfloxacin on CNS functions and urinary hydroxyproline in mice. Pharmacol Res. 2006 Aug;54(2):111-7. doi: 10.1016/j.phrs.2006.03.004. Epub 2006 Mar 22. PMID: 16701999.
1: Schentag JJ. Sparfloxacin: a review. Clin Ther. 2000 Apr;22(4):372-87; discussion 371. Review. PubMed PMID: 10823360.
2: Finch RG. A review of worldwide experience with sparfloxacin in the treatment of community-acquired pneumonia and acute bacterial exacerbations of chronic bronchitis. Int J Antimicrob Agents. 1999 Jun;12(1):5-17. Review. PubMed PMID: 10389642.
3: Martin SJ, Meyer JM, Chuck SK, Jung R, Messick CR, Pendland SL. Levofloxacin and sparfloxacin: new quinolone antibiotics. Ann Pharmacother. 1998 Mar;32(3):320-36. Review. PubMed PMID: 9533064.
4: Stein GE, Havlichek DH. Sparfloxacin: potential clinical and economic impact in the treatment of respiratory infections. Pharmacotherapy. 1997 Nov-Dec;17(6):1139-47. Review. PubMed PMID: 9399598.
5: Goa KL, Bryson HM, Markham A. Sparfloxacin. A review of its antibacterial activity, pharmacokinetic properties, clinical efficacy and tolerability in lower respiratory tract infections. Drugs. 1997 Apr;53(4):700-25. Review. PubMed PMID: 9098667.
6: Goldstein EJ. Possible role for the new fluoroquinolones (levofloxacin, grepafloxacin, trovafloxacin, clinafloxacin, sparfloxacin, and DU-6859a) in the treatment of anaerobic infections: review of current information on efficacy and safety. Clin Infect Dis. 1996 Dec;23 Suppl 1:S25-30. Review. PubMed PMID: 8953103.
7: Cohen MA, Yoder SL, Talbot GH. Sparfloxacin worldwide in vitro literature: isolate data available through 1994. Diagn Microbiol Infect Dis. 1996 Jun;25(2):53-64. Review. PubMed PMID: 8882890.
8: Jaillon P, Morganroth J, Brumpt I, Talbot G. Overview of electrocardiographic and cardiovascular safety data for sparfloxacin. Sparfloxacin Safety Group. J Antimicrob Chemother. 1996 May;37 Suppl A:161-7. Review. PubMed PMID: 8737135.
9: Wise R, Honeybourne D. A review of the penetration of sparfloxacin into the lower respiratory tract and sinuses. J Antimicrob Chemother. 1996 May;37 Suppl A:57-63. Review. PubMed PMID: 8737125.
10: Montay G. Pharmacokinetics of sparfloxacin in healthy volunteers and patients: a review. J Antimicrob Chemother. 1996 May;37 Suppl A:27-39. Review. PubMed PMID: 8737123.
11: Baquero F, Cantón R. In-vitro activity of sparfloxacin in comparison with currently available antimicrobials against respiratory tract pathogens. J Antimicrob Chemother. 1996 May;37 Suppl A:1-18. Review. PubMed PMID: 8737121.
12: [Significant role of newer quinolone antimicrobials in respiratory tract infection: focused on sparfloxacin]. Jpn J Antibiot. 1994 Oct;47(10):1241-58. Review. Japanese. PubMed PMID: 7807686.
13: Shimada J, Nogita T, Ishibashi Y. Clinical pharmacokinetics of sparfloxacin. Clin Pharmacokinet. 1993 Nov;25(5):358-69. Review. PubMed PMID: 8287631.
14: Richard P, Gutmann L. Sparfloxacin and other new fluoroquinolones. J Antimicrob Chemother. 1992 Dec;30(6):739-44. Review. PubMed PMID: 1337749.
