Nadifloxacin | CAS#124858-35-1 | DNA gyrase inhibitor

MedKoo Cat#: 540307 | Name: Nadifloxacin

Description:

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

Nadifloxacin is a bacterial DNA gyrase inhibitor used to treat acne vulgaris. It inhibits Proponibacterium-stimulated cytokine expression and decreases production of oxidative radicals by neutrophils.

Chemical Structure

Nadifloxacin

CAS#124858-35-1

Theoretical Analysis

MedKoo Cat#: 540307

Name: Nadifloxacin

CAS#: 124858-35-1

Chemical Formula: C19H21FN2O4

Exact Mass: 360.1485

Molecular Weight: 360.38

Elemental Analysis: C, 63.32; H, 5.87; F, 5.27; N, 7.77; O, 17.76

Price and Availability

Size	Price	Availability
1g	USD 250.00	Ready to ship
2g	USD 450.00	Ready to ship
5g	USD 950.00	2 Weeks

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Related CAS #

No Data

Synonym

Nadifloxacine; Nadixa; OPC-7251; OPC7251; OPC 7251

IUPAC/Chemical Name

9-fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

InChi Key

JYJTVFIEFKZWCJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H21FN2O4/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21/h8-11,23H,2-7H2,1H3,(H,25,26)

SMILES Code

O=C(C1=CN2C(C)CCC3=C2C(C1=O)=CC(F)=C3N4CCC(O)CC4)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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C20B07B07

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Nadifloxacin(OPC7251) is a topical fluoroquinolone antibiotic for the treatment of acne vulgaris that inhibits the enzyme DNA gyrase.

In vitro activity:

TBD

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	55.50

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 360.38 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:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: Narayanan V, Motlekar S, Kadhe G, Bhagat S. Efficacy and safety of nadifloxacin for bacterial skin infections: results from clinical and post-marketing studies. Dermatol Ther (Heidelb). 2014 Dec;4(2):233-48. doi: 10.1007/s13555-014-0062-1. Epub 2014 Sep 12. PubMed PMID: 25212256; PubMed Central PMCID: PMC4257952. 2: Jung JY, Kwon HH, Yeom KB, Yoon MY, Suh DH. Clinical and histological evaluation of 1% nadifloxacin cream in the treatment of acne vulgaris in Korean patients. Int J Dermatol. 2011 Mar;50(3):350-7. doi: 10.1111/j.1365-4632.2010.04701.x. PubMed PMID: 21342170. 3: Shinde U, Pokharkar S, Modani S. Design and evaluation of microemulsion gel system of nadifloxacin. Indian J Pharm Sci. 2012 May;74(3):237-47. doi: 10.4103/0250-474X.106066. PubMed PMID: 23439454; PubMed Central PMCID: PMC3574534. 4: Takigawa M, Tokura Y, Shimada S, Furukawa F, Noguchi N, Ito T; Acne Study Group. Clinical and bacteriological evaluation of adapalene 0.1% gel plus nadifloxacin 1% cream versus adapalene 0.1% gel in patients with acne vulgaris. J Dermatol. 2013 Aug;40(8):620-5. doi: 10.1111/1346-8138.12189. Epub 2013 Jun 3. PubMed PMID: 23724808. 5: Kobayashi M, Nakagawa T, Fukamachi K, Nakamura M, Tokura Y. Efficacy of combined topical treatment of acne vulgaris with adapalene and nadifloxacin: a randomized study. J Dermatol. 2011 Dec;38(12):1163-6. doi: 10.1111/j.1346-8138.2011.01280.x. Epub 2011 Oct 18. PubMed PMID: 22007904. 6: Inoue Y, Matsumoto M, Kimura M, Tanaka T, Kanamoto I. Comparison of the properties of brand-name and generic nadifloxacin creams. Medicina (Kaunas). 2011;47(11):616-22. PubMed PMID: 22286577. 7: Wilhelm KP, Wilhelm D, Neumeister C, Zsolt I, Schwantes U. Lack of irritative potential of nadifloxacin 1% when combined with other topical anti-acne agents. Clin Exp Dermatol. 2012 Mar;37(2):112-7. doi: 10.1111/j.1365-2230.2011.04214.x. Epub 2011 Nov 21. PubMed PMID: 22103435. 8: Shah BJ, Sumathy TK, Dhurat RS, Torsekar RG, Viswanath V, Mukhi JI, Kadhe G, Ahirrao P. Efficacy and tolerability of topical fixed combination of nadifloxacin 1% and adapalene 0.1% in the treatment of mild to moderate acne vulgaris in Indian patients: a multicenter, open-labelled, prospective study. Indian J Dermatol. 2014 Jul;59(4):385-9. doi: 10.4103/0019-5154.135492. PubMed PMID: 25071260; PubMed Central PMCID: PMC4103277. 9: Kumar A, Agarwal SP, Ahuja A, Ali J, Choudhry R, Baboota S. Preparation, characterization, and in vitro antimicrobial assessment of nanocarrier based formulation of nadifloxacin for acne treatment. Pharmazie. 2011 Feb;66(2):111-4. PubMed PMID: 21434572. 10: Müller S, Ebnöther M, Itin P. Green Nail Syndrome (Pseudomonas aeruginosa Nail Infection): Two Cases Successfully Treated with Topical Nadifloxacin, an Acne Medication. Case Rep Dermatol. 2014 Jul 19;6(2):180-4. doi: 10.1159/000365863. eCollection 2014 May. PubMed PMID: 25202260; PubMed Central PMCID: PMC4152926. 11: Kawamoto T, Tayama Y, Sawa A, Monde T, Sashima S, Yoshioka M, Miyake K, Morita S, Kihira K. [Effect of the admixture of tetracycline and nadifloxacin ointments on their stability and their antibacterial activity]. Yakugaku Zasshi. 2008 Aug;128(8):1221-6. Japanese. PubMed PMID: 18670189. 12: Choudhury S, Chatterjee S, Sarkar DK, Dutta RN. Efficacy and safety of topical nadifloxacin and benzoyl peroxide versus clindamycin and benzoyl peroxide in acne vulgaris: A randomized controlled trial. Indian J Pharmacol. 2011 Nov;43(6):628-31. doi: 10.4103/0253-7613.89815. PubMed PMID: 22144763; PubMed Central PMCID: PMC3229774. 13: Murata K, Sugita K, Kobayashi M, Kabashima K, Tokura Y. Nadifloxacin downmodulates antigen-presenting functions of epidermal Langerhans cells and keratinocytes. J Dermatol Sci. 2006 May;42(2):91-9. Epub 2006 Jan 23. PubMed PMID: 16431082. 14: Alba V, Urban E, Angeles Dominguez M, Nagy E, Nord CE, Palacín C, Vila J. In vitro activity of nadifloxacin against several Gram-positive bacteria and analysis of the possible evolution of resistance after 2 years of use in Germany. Int J Antimicrob Agents. 2009 Mar;33(3):272-5. doi: 10.1016/j.ijantimicag.2008.08.024. Epub 2008 Dec 17. PubMed PMID: 19095414. 15: Plewig G, Holland KT, Nenoff P. Clinical and bacteriological evaluation of nadifloxacin 1% cream in patients with acne vulgaris: a double-blind, phase III comparison study versus erythromycin 2% cream. Eur J Dermatol. 2006 Jan-Feb;16(1):48-55. PubMed PMID: 16436342. 16: Hosoda S, Komine M, Karakawa M, Tsuda H, Ohtsuki M. Nadifloxacin downregulates the production of matrix metalloproteinases in the human epidermal keratinocyte cell line HaCaT. J Dermatol. 2012 Oct;39(10):855-7. doi: 10.1111/j.1346-8138.2011.01466.x. Epub 2012 Jan 4. PubMed PMID: 22220987. 17: Akamatsu H, Sasaki H, Kurokawa I, Nishijima S, Asada Y, Niwa Y. Effect of nadifloxacin on neutrophil functions. J Int Med Res. 1995 Jan-Feb;23(1):19-26. PubMed PMID: 7774755. 18: Tunca M, Akar A, Ozmen I, Erbil H. Topical nadifloxacin 1% cream vs. topical erythromycin 4% gel in the treatment of mild to moderate acne. Int J Dermatol. 2010 Dec;49(12):1440-4. doi: 10.1111/j.1365-4632.2010.04601.x. PubMed PMID: 21091683. 19: Jacobs MR, Appelbaum PC. Nadifloxacin: a quinolone for topical treatment of skin infections and potential for systemic use of its active isomer, WCK 771. Expert Opin Pharmacother. 2006 Oct;7(14):1957-66. Review. PubMed PMID: 17020421. 20: Oizumi N, Kawabata S, Hirao M, Watanabe K, Okuno S, Fujiwara T, Kikuchi M. Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus. J Infect Chemother. 2001 Sep;7(3):191-4. PubMed PMID: 11810583.