Norfloxacin | CAS# 70458-96-7 (free base) | chemotherapeutic antibacterial agent

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

MedKoo CAT#: 318379

CAS#: 70458-96-7 (free base)

Description: Norfloxacin is a synthetic chemotherapeutic antibacterial agent occasionally used to treat common as well as complicated urinary tract infections. It is a first generation synthetic fluoroquinolone (quinolone) and is approved for the treatment of urinary tract infections, prostatitis, and sexually transmitted diseases, although it is no longer used for the latter due to bacterial resistance.

Chemical Structure

Norfloxacin

CAS# 70458-96-7 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318379
Name: Norfloxacin
CAS#: 70458-96-7 (free base)
Chemical Formula: C16H18FN3O3
Exact Mass: 319.13
Molecular Weight: 319.331
Elemental Analysis: C, 60.18; H, 5.68; F, 5.95; N, 13.16; O, 15.03

Price and Availability

Size	Price	Availability	Quantity
100g	USD -1
200g	USD -1
100mg	USD 150
200mg	USD 200
500mg	USD 250
1g	USD 300
2g	USD 350
5g	USD 400
10g	USD 450
20g	USD 550
50g	USD 650
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 70458-96-7 (free base); 68077-27-0 (HCl); 85181-48-2 (glutamate); 100587-52-8 (succinil)

Synonym: Norfloxacin, AM-715, MK-366, Noroxin, Chibroxin

IUPAC/Chemical Name: 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

InChi Key: OGJPXUAPXNRGGI-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)

SMILES Code: O=C(C1=CN(CC)C2=C(C=C(F)C(N3CCNCC3)=C2)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, 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:

Product Data:

Product Data

Instruction:

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Biological target:	Norfloxacin (MK-0366) is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.
In vitro activity:	Treatment with norfloxacin down-regulated Leptospira-induced IL-1β and TNF-α both in vivo and vitro models. Further study showed that norfloxacin inhibited Leptospira-induced phosphorylation of p65 and ERK. Norfloxacin also inhibited the Leptospira-induced NLRP3 inflammasome activation with the increased level of Na/K-ATPase Pump β1 subunit and decreased level of Kcnk6. These results indicated that norfloxacin suppressed Leptospira-induced inflammation through inhibiting p65 and ERK phosphorylation and NLRP3 inflammasome activation. Reference: Microb Pathog. 2022 Jan;162:105315. https://pubmed.ncbi.nlm.nih.gov/34826552/
In vivo activity:	Topical treatment with norfloxacin significantly suppressed the increase in the skin severity score in NC/Nga mice with AD-like skin lesions. This suppressive effect was associated with a decrease in the production of IFN-g and IL-4 in auricular lymph node cells. The present results show that topical application of norfloxacin inhibits the development of AD-like skin lesions in NC/Nga mice. This suggests that topical application of norfloxacin to AD lesions colonized with S. aureus would act on both superficial S. aureus and epidermal LCs, thus possibly inhibiting the development of Th1 and Th2 cells in vivo, and controlling the severity of AD. Reference: J Pharm Pharm Sci. 2019 Apr 11;22(1):122-130. https://pubmed.ncbi.nlm.nih.gov/30974054/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	5.0	15.66
	DMSO	3.5	10.96
	PBS (pH 7.2)	0.5	1.57
	Water	1.0	3.13

Preparing Stock Solutions

The following data is based on the product molecular weight 319.33 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. Xie X, Zhang W, Chen X, Wu D, Cao Y. Norfloxacin suppresses Leptospira-induced inflammation through inhibiting p65 and ERK phosphorylation and NLRP3 inflammasome activation. Microb Pathog. 2022 Jan;162:105315. doi: 10.1016/j.micpath.2021.105315. Epub 2021 Nov 24. PMID: 34826552. 2. Yang T, Fan TJ, Xu B. Norfloxacin induces apoptosis and necroptosis in human corneal epithelial cells. Toxicol In Vitro. 2020 Aug;66:104868. doi: 10.1016/j.tiv.2020.104868. Epub 2020 Apr 19. PMID: 32320760. 3. Matsui K, Kashima A, Motegi A. Norfloxacin, a Fluoroquinolone Antibiotic, Inhibits Langerhans Cell-Mediated Th1 and Th2 Cell Development. J Pharm Pharm Sci. 2019 Apr 11;22(1):122-130. doi: 10.18433/jpps30335. PMID: 30974054. 4. Tazi KA, Moreau R, Hervé P, Dauvergne A, Cazals-Hatem D, Bert F, Poirel O, Rabiller A, Lebrec D. Norfloxacin reduces aortic NO synthases and proinflammatory cytokine up-regulation in cirrhotic rats: role of Akt signaling. Gastroenterology. 2005 Jul;129(1):303-14. doi: 10.1053/j.gastro.2005.04.016. PMID: 16012955.
In vitro protocol:	1. Xie X, Zhang W, Chen X, Wu D, Cao Y. Norfloxacin suppresses Leptospira-induced inflammation through inhibiting p65 and ERK phosphorylation and NLRP3 inflammasome activation. Microb Pathog. 2022 Jan;162:105315. doi: 10.1016/j.micpath.2021.105315. Epub 2021 Nov 24. PMID: 34826552. 2. Yang T, Fan TJ, Xu B. Norfloxacin induces apoptosis and necroptosis in human corneal epithelial cells. Toxicol In Vitro. 2020 Aug;66:104868. doi: 10.1016/j.tiv.2020.104868. Epub 2020 Apr 19. PMID: 32320760.
In vivo protocol:	1. Matsui K, Kashima A, Motegi A. Norfloxacin, a Fluoroquinolone Antibiotic, Inhibits Langerhans Cell-Mediated Th1 and Th2 Cell Development. J Pharm Pharm Sci. 2019 Apr 11;22(1):122-130. doi: 10.18433/jpps30335. PMID: 30974054. 2. Tazi KA, Moreau R, Hervé P, Dauvergne A, Cazals-Hatem D, Bert F, Poirel O, Rabiller A, Lebrec D. Norfloxacin reduces aortic NO synthases and proinflammatory cytokine up-regulation in cirrhotic rats: role of Akt signaling. Gastroenterology. 2005 Jul;129(1):303-14. doi: 10.1053/j.gastro.2005.04.016. PMID: 16012955.

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1: Hubicka U, Krzek J, Walczak M. Stability of ciprofloxacin and norfloxacin in the presence and absence of metal ions in acidic solution. Pharm Dev Technol. 2010 Sep-Oct;15(5):532-44. doi: 10.3109/10837450903338379. Review. PubMed PMID: 19842796.

2: Chou CJ, Membrez M, Blancher F. Gut decontamination with norfloxacin and ampicillin enhances insulin sensitivity in mice. Nestle Nutr Workshop Ser Pediatr Program. 2008;62:127-37; discussion 137-40. doi: 10.1159/000146256. Review. PubMed PMID: 18626197.

3: Padeĭskaia EN. [Norfloxacin: more than 20 years of clinical use, the results and place among fluoroquinolones in modern chemotherapy for infections]. Antibiot Khimioter. 2003;48(9):28-36. Review. Russian. PubMed PMID: 15002177.

4: Miano L, Goldoni S, Tubaro A, Paradiso Galatioto G, Gandolfi P. Review of norfloxacin in lower urinary tract infections. Eur Urol. 1990;17 Suppl 1:13-8. Review. PubMed PMID: 2191864.

5: Wolfson JS, Hooper DC. Norfloxacin: a new targeted fluoroquinolone antimicrobial agent. Ann Intern Med. 1988 Feb;108(2):238-51. Review. PubMed PMID: 3277508.

6: Nalin DR. Bacterial resistance to norfloxacin and other newer quinolones: pattern and prospects. Eur J Cancer Clin Oncol. 1988;24 Suppl 1:S55-61. Review. PubMed PMID: 3280327.

7: Edlund C, Nord CE. Manipulation of the oropharyngeal and intestinal microflora by norfloxacin: microbiological and clinical aspects. Scand J Infect Dis Suppl. 1988;56:14-21. Review. PubMed PMID: 3074461.

8: Stein GE. Review of the bioavailability and pharmacokinetics of oral norfloxacin. Am J Med. 1987 Jun 26;82(6B):18-21. Review. PubMed PMID: 3300308.

9: Goldstein EJ. Norfloxacin, a fluoroquinolone antibacterial agent. Classification, mechanism of action, and in vitro activity. Am J Med. 1987 Jun 26;82(6B):3-17. Review. PubMed PMID: 3111257.

10: Norrby SR. Principles for targeted antibiotic use in urinary tract and enteric infections: a review with special emphasis on norfloxacin. Scand J Infect Dis Suppl. 1986;48:7-19. Review. PubMed PMID: 3535056.

11: Ruiz-Palacios GM. Norfloxacin in the treatment of bacterial enteric infections. Scand J Infect Dis Suppl. 1986;48:55-63. Review. PubMed PMID: 3535054.

12: Holmes B, Brogden RN, Richards DM. Norfloxacin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1985 Dec;30(6):482-513. Review. PubMed PMID: 3908074.

13: Wise R. Norfloxacin--a review of pharmacology and tissue penetration. J Antimicrob Chemother. 1984 May;13 Suppl B:59-64. Review. PubMed PMID: 6234277.

14: Lucena MI, Andrade RJ, Sanchez-Martinez H, Perez-Serrano JM, Gomez-Outes A. Norfloxacin-induced cholestatic jaundice. Am J Gastroenterol. 1998 Nov;93(11):2309-11. Review. PubMed PMID: 9820434.

15: Stojiljković MP, Jovanović D. [Norfloxacin--its current role in pharmacotherapy]. Vojnosanit Pregl. 1998 May-Jun;55(3):291-304. Review. Serbian. PubMed PMID: 9720445.

16: Hadimeri H, Almroth G, Cederbrant K, Eneström S, Hultman P, Lindell A. Allergic nephropathy associated with norfloxacin and ciprofloxacin therapy. Report of two cases and review of the literature. Scand J Urol Nephrol. 1997 Oct;31(5):481-5. Review. PubMed PMID: 9406312.

17: Schaeffer AJ. Review of norfloxacin in complicated and recurrent urinary tract infections. Eur Urol. 1990;17 Suppl 1:19-23. Review. PubMed PMID: 2191865.

18: Hooper DC, Wolfson JS. Norfloxacin, ciprofloxacin, and ofloxacin: current clinical roles. Curr Clin Top Infect Dis. 1989;10:194-240. Review. PubMed PMID: 2679694.

19: Karb VB. Two new fluoroquinolones: ciprofloxacin and norfloxacin. J Neurosci Nurs. 1988 Oct;20(5):327-28. Review. PubMed PMID: 2976793.

20: Ueda Y, Matsumoto F. [Current antimicrobial agent series III: Norfloxacin]. Jpn J Antibiot. 1988 Jul;41(7):782-96. Review. Japanese. PubMed PMID: 3050183.

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