Irloxacin
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MedKoo CAT#: 576764

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

Description: 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

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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: 300.091
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 Quantity
1.0mg USD 90.0 Ready to ship
5.0mg USD 350.0 Ready to ship
10.0mg USD 550.0 Ready to ship
25.0mg USD 950.0 Ready to ship
50.0mg USD 1650.0 Ready to ship
100.0mg USD 2950.0 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

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.0 0.0

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.

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
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. 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.

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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.