Irloxacin | CAS# 91524-15-1 | Biochemical

MedKoo Cat#: 576764 | Name: Irloxacin

Description:

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

Irloxacin is a new quinolone derivative, and shows greater activity with an acid pH. It has a good in vitro antimicrobial spectrum against both gram-positive and gram-negative bacteria. In vitro activity of irloxacin against mycobacteria (20 M. tuberculosis, 17 M. avium, 5 Mycobacterium bovis, 5 Mycobacterium chelonae, 5 Mycobacterium fortuitum and 1 Mycobacterium gadium) using the Bactec at pH 6.8 and 5.0, with other quinolones (ofloxacin, ciprofloxacin, pefloxacin and 27753 RP) were compared. All quinolones tested showed good activity against mycobacteria at pH 6.8 and 5.0. Irloxacin at pH 5.0 had a greater activity against M. avium.

Chemical Structure

Irloxacin

CAS#91524-15-1 (free acid)

Theoretical Analysis

MedKoo Cat#: 576764

Name: Irloxacin

CAS#: 91524-15-1 (free acid)

Chemical Formula: C16H13FN2O3

Exact Mass: 300.0910

Molecular Weight: 300.29

Elemental Analysis: C, 64.00; H, 4.36; F, 6.33; N, 9.33; O, 15.98

Price and Availability

Size	Price	Availability
1mg	USD 90.00	Ready to ship
5mg	USD 350.00	Ready to ship
10mg	USD 550.00	Ready to ship
25mg	USD 950.00	Ready to ship
50mg	USD 1,650.00	Ready to ship
100mg	USD 2,950.00	Ready to ship

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Related CAS #

122949-49-9 (sodium) 91524-15-1 (free acid)

Synonym

E 3432; E3432; E-3432; Irloxacin; Pirfloxacin

IUPAC/Chemical Name

3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)-

InChi Key

RZLHGQLYNZQZQQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H13FN2O3/c1-2-18-9-11(16(21)22)15(20)10-7-12(17)14(8-13(10)18)19-5-3-4-6-19/h3-9H,2H2,1H3,(H,21,22)

SMILES Code

O=C(C1=CN(CC)C2=C(C=C(F)C(N3C=CC=C3)=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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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#YXM220304

QC Data

View QC data: current batch, Lot#YXM220304

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Irloxacin (Pirfloxacin) is a quinolone antibacterial agent that shows greater activity with an acidic pH and has a good in vitro antimicrobial spectrum against both gram-positive and gram-negative bacteria.

In vitro activity:

TBD

In vivo activity:

Embryotoxicity studies on irloxacin (6-fluorine-7-(pyrrol-1-yl)-1-ethyl-1,4-dihydro-4-oxo-quinolone-3-carboxylic acid, CAS-91524-15-1), a new fluoroquinolone antibacterial agent, were performed in rats and rabbits. Oral administration of irloxacin during the fetal period of organogenesis to pregnant rats and rabbits at dose levels of up to 1000 and 350 mg/kg/d, respectively, elicited no evidence of teratogenicity. During the first days of treatment, transient stasis in body weight increase was observed in rat dams receiving doses of 350 or 1000 mg/kg/d, and reduced food consumption was observed in those receiving 1000 mg/kg/d. Necropsy on day 20 of gestation showed dosage related increase in liver and kidney weights in all rat treated groups. Rabbit dams receiving 350 mg/kg/d showed during the first days of treatment decrease in body weight, and decreased food consumption and faecal output. Also, four females receiving 350 mg/kg/d aborted between days 18 and 20 of gestation. Rat fetuses in the 350 and 1000 mg/kg/d showed decreased body weight, and a decrease in placental weights was observed in the 1000 mg/kg/d group. No retardations or malformations were observed in rat or rabbit fetuses at any tested dose level. Reference: Arzneimittelforschung. 2003;53(2):121-5. https://pubmed.ncbi.nlm.nih.gov/12642968/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

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 300.29 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. Guzmán A, García C, Marín AP, Willoughby C, Demestre I. Developmental toxicity studies of the quinolone antibacterial agent irloxacin in rats and rabbits. Arzneimittelforschung. 2003;53(2):121-5. doi: 10.1055/s-0031-1297082. PMID: 12642968. 2. Guzmán A, García C, Demestre I. Subchronic toxicity of the new quinolone antibacterial agent irloxacin in beagle dogs. Arzneimittelforschung. 2000 May;50(5):485-94. doi: 10.1055/s-0031-1300234. PMID: 10858877.

In vitro protocol:

TBD

In vivo protocol:

1: Yang M, Yang Y, Lei M, Ye C, Zhao C, Xu J, Wu K, Yu M. Experimental studies on soft contact lenses for controlled ocular delivery of pirfinedone: in vitro and in vivo. Drug Deliv. 2016 Nov;23(9):3538-3543. doi: 10.1080/10717544.2016.1204570. Epub 2016 Jul 17. PMID: 27331555. 2: Guerrini V, De Rosa M, Pasquini S, Mugnaini C, Brizzi A, Cuppone AM, Pozzi G, Corelli F. New fluoroquinolones active against fluoroquinolones-resistant Mycobacterium tuberculosis strains. Tuberculosis (Edinb). 2013 Jul;93(4):405-11. doi: 10.1016/j.tube.2013.02.017. Epub 2013 Mar 22. PMID: 23523640. 3: Guzmán A, García C, Marín AP, Willoughby C, Demestre I. Developmental toxicity studies of the quinolone antibacterial agent irloxacin in rats and rabbits. Arzneimittelforschung. 2003;53(2):121-5. doi: 10.1055/s-0031-1297082. PMID: 12642968. 4: Guzmán A, García C, Demestre I. Subchronic toxicity of the new quinolone antibacterial agent irloxacin in beagle dogs. Arzneimittelforschung. 2000 May;50(5):485-94. doi: 10.1055/s-0031-1300234. PMID: 10858877. 5: Guzmán A, García C, Demestre I. Acute and subchronic toxicity studies of the new quinolone antibacterial agent irloxacin in rodents. Arzneimittelforschung. 1999 May;49(5):448-56. doi: 10.1055/s-0031-1300441. PMID: 10367108. 6: Casal M, Gutierrez J, Ruiz P, Moreno G. Preliminary study of the in vitro activity of irloxacin against mycobacteria. Chemotherapy. 1995 May- Jun;41(3):204-7. doi: 10.1159/000239345. PMID: 7656667. 7: Van Caekenberghe D. Comparative in-vitro activities of ten fluoroquinolones and fusidic acid against Mycobacterium spp. J Antimicrob Chemother. 1990 Sep;26(3):381-6. doi: 10.1093/jac/26.3.381. PMID: 2228828. 8: García-Rodríguez JA, García Sánchez JE, Muñoz Bellido JL, Trujillano I. In vitro activities of irloxacin and E-3846, two new quinolones. Antimicrob Agents Chemother. 1990 Jun;34(6):1262-7. doi: 10.1128/AAC.34.6.1262. PMID: 2393288; PMCID: PMC171797. 9: Massa S, Corelli F, Mai A, Artico M, Panico S, Simonetti N. Research on antibacterial and antifungal agents. XI. New antibacterial quinolones related to pirfloxacin. Farmaco. 1989 Sep;44(9):779-93. PMID: 2604833. 10: Coll R, Esteve M, Moros M, Parés J, Xicota MA. Comparative activity of three new fluoroquinolones. Chemioterapia. 1987 Jun;6(2 Suppl):152-3. PMID: 3509374. 11: Coll R, Esteve M, Moros M, Xicota MA, Parés J. In vitro antibacterial activity of irloxacin (E-3432) on clinical isolates. Drugs Exp Clin Res. 1987;13(2):75-7. PMID: 3582134. 12: Artico M, Corelli F, Massa S, Stefancich G, Panico S, Simonetti N. Ricerche su agenti antibatterici ed antifungini. Nota VI. Pirflossacina e composti correlati: studi sintetici e microbiologici [Antibacterial and antifungal agents. VI. Pirfloxacin and related compounds: synthetic and microbiological studies]. Farmaco Sci. 1986 May;41(5):366-80. Italian. PMID: 3087770. 13: Stefancich G, Artico M, Corelli F, Massa S, Panico S, Simonetti N. 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)-quinoline-3-carb oxylic acid, a new fluorinated compounds of oxacin family with high broad-spectrum antibacterial activities. Farmaco Sci. 1985 Apr;40(4):237-48. PMID: 3926533.