Flumequine and Balofloxacin

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Nagdat Majd Mahouk

LAB GROUP: F₂

Lab Instructors:

T.A/

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Spring 2015

Table of Contents:

1. Introduction on (Flumequine) pg. 3 and (Balofloxacin) pg. 4
2. Discussion on (Flumequine) pg. 5, 6, 7 and (Balofloxacin) pg. 8, 9, 10
3. Conclusion pg. 11
4. Reference pg. 12

Flumequine:

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The first of the quinolone family is the nalidixic acid. The drug was followed by the floroquinolones including flumequine which is a 1st generation agent in the floroquinolones. The first generation including flumequine had a variety of problems such as:

• Limited activity
• poor distribution
• tendon ruptures
• Hepatotoxicity and additive effect on neurological disorders ex: myasthenia gravis

All of the first generation drugs were used for the treatment of infections in the urinary tract. The benzo quinolzine (flumequine) was invented in 1973 by (rikker labs) a german inventors. Flumequine is known to be the first of the quinolone family to include a fluoride at carbon number six on the skeleton of the quinolone compound. Although flumequine is basically the first of all floroquinolones it is frequently overlooked upon classification of this class of drugs through generations; it was omitted from the list. It is more often used for the treatment of farm animals and on certain cases pets. And as follows the use in humans is for infections in the urinary tract. It was originally used only for urinary tract infections until reports of toxicity were filed reporting anaphylactic shock and degrees of damage in the liver. The (FDA) food and drug administration made a request on all the quinolone and floroquinolone boxes to be delivered to contain a black boxed warning thus, notifying the risks of sudden ruptures in the tendon which basically includes the flumequine. As well letters were sent to physicians based on the FDA's request to notify the doctors. The tendon complications were also exhibited in flumequine.

The majority of floroquinolone generic versions did not include the black boxed warning in 2009 September as well some reports were filed to claim that this information was never distributed or shared among pharmacists and some products to this day still are shipped without the warning or medication guide that the physicians and pharmacists can distribute.

Uses (licensed):

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Infections in the urinary tract

Balofloxacin:

Balofloxacin is often potent as an antibacterial agent. It has a broad spectrum bactericidal activity. It is less toxic than other fluoroquinolones. The distinction between a quinolone drug and a fluoroquinolone drug is the addition of fluorine to the basic pharmacophore, which causes a fluorinated drug. Quinolones and fluoroquinolones terms are often used interchangeably regardless of this distinction. Balofloxacin is a third generation fluoroquinolone.

A meta-analysis of skin infections and fluoroquinolones showed that the fluoroquinolones are more associated with unfavorable reactions than beta lactam. However, the increase was due to a slight to moderate rate of nausea and diarrhea higher. Enough to cause serious side effects withdrawal of the trial occurred at similar rates.

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Rarely, fluoroquinolones have been associated with serious and adverse effects on the musculoskeletal system, cardiovascular system, central nervous system and peripheral nervous system, circulatory system, the maxillofacial system, endocrine system, gastrointestinal system the urological system, liver, brain, skin, and sensory systems such as sight, hearing, touch, smell and taste. After a single dose toxic reactions had been reported to occur.

Uses:

Uncomplicated infections of the urinary tract

Chemical structure:

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Flumequine:

Chemical structure and formula:

C (14) H (12) F (1) N (1) O (3)

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IUPAC name:

9-fluoro -6, 7 dihydro -5 methyl -1 oxo -1H, 5H -benzo quinolizine -2- carboxylic acid

Mode of action:

Flumequine is mainly an antibiotic that is broad spectrum and mostly active against gram positive bacteria and gram negative. Mechanism works through the inhibition of gyrase DNA, topoisomerase specifically type 2 and type 4; they are enzymes that are responsible for bacterial DNA segregation therefore by inhibiting them the bacteria cannot replicate hence, inhibition of cell division. This mechanism might also alter mammalian cell division. Basically the drugs of high activity could lead to toxic effects in mammals. The report of DNA damage was first filed in 1986, its mechanism of cytotoxicity is still unknown.

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Dosage forms:

For veterinary forms: Oral solutions (10-20%) prescription required

For human forms: Oral tablets (400mg) notice: it is discontinued

20% solution

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Tablet formulation stopped

Synthesis of flumequine:

Structure activity relationship (SAR):

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• The fluorine that is present at carbon number six which enhances the inhibition of gyrase and cellular penetration.
• The carbon number seven constituent was found to control cell permeability according to the properties of the constituent.
• Substitution of N number 1 is essential in obtaining the anti-bacterial properties.
• The introduction of a butyl group at N number 1 enhances the activity against the gram positive bacteria and little or minimal reduction of activity against gram negative bacteria.
• At position two the addition of nitrogen did show an improvement of the pharmacokinetic properties.
• At positions 4 and 3 they do have a link with the keto and carboxylic group which is an essential thing for binding to the gyrase DNA.
• At position number 5 the substitution by small groups like amino, nitro, halogens and alkyl groups could improve the tissue distribution and absorption. Though suggestions were raised that the substitution at position 5 could decrease the anti-bacterial properties.
• At position 6 the substitution by F, H, Br, Cl, nitro, methyl and Cyanide would actually increase the potency of anti-bacterial activity by means of improving the binding and penetration abilities.

Metabolism:

Flumequine is known to have good absorption thus, well absorbed and is mainly excreted in feces and urine as a glucuronide conjugates according to the parent drug and active ingredient of metabolism which is flumequine 7-hydroxy. The drug is eliminated within 168 hours after dosing. Major residue was found in chickens, pigs and sheep to be in the form of flumequine 7-hydroxy it was found in minimal amounts. The detection of the parent drug was only found in trout. Metabolism can be summarized as well absorbed and metabolized in the liver.

Balofloxacin:

IUPAC:

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1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylaminopiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid

Synthesis:

Mode of action

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First and second generation fluoroquinolone selectively inhibit the field of ligase topoisomerase II, leaving two areas nuclease intact. This modification, combined with the constant action in the bacterial cell by topoisomerase II, results in fragmentation of DNA through nuclease activity domains of intact enzymes. fluoroquinolones that are third and fourth generation are more selective for the ligase domain topoisomerase IV and therefore improved the gram positive coverage.

Fluoroquinolones can enter cells through porins easily thus, could be used for the treatment of pathogens that are intracellular such as Mycoplasma pneumoniae and Legionella pneumophila. Too many bacteria that are gram-negative, the target is the DNA gyrase, in turn the topoisomerase IV is the target of many Gram-positive bacteria. Some compounds of this class were found to inhibit the synthesis of mitochondrial DNA.

Dosage forms:

Tablets 100-400 mg oral

Metabolism:

Pharmacokinetics of balofloxacin, the new fluoroquinolone, was a study conducted on mice, dogs and rats through liquid chromatography (high-performance). The bioavailabilities oral means of balofloxacin it was obtained through calculation of the AUC (area under the curve) after intravenous and oral in mice, rats and dogs 87.50 and 87.73%, respectively, suggesting that was absorbed almost entirely balofloxacin in rats and dogs, but not in mice after single oral administration. The average elimination half-life in plasma after intravenous injection in mice, rats and dogs are 0.92, 1.33 and 6.38 hours, respectively. I mean cumulative urinary excretion rate unchanged balofloxacin within 24 hours of oral administration of balofloxacin in dogs, mice and rats respectively. May secrete a small part of the metabolism in the urine as glucuronide balofloxacin and N-desmethyl balofloxacin in these species. After oral administration of balofloxacin in a dose of 100 mg / kg in rats, and was for a long period of absorption compared with those after administration in doses of 5 and 20 mg / kg. The plasma concentration-time profiles and pharmacological parameters of balofloxacin in male mice similar to those found in female mice, suggesting a lack of sex-related differences. Once a day for 21 days, multiple departments were not affected by this drug in mice of balofloxacin formations.

Structure activity relationship (SAR):

• The fluorine that is present at carbon number six which enhances the inhibition of gyrase and cellular penetration.
• The carbon number seven constituent was found to control cell permeability according to the properties of the constituent.
• Substitution of N number 1 is essential in obtaining the anti-bacterial properties.
• The introduction of a butyl group at N number 1 enhances the activity against the gram positive bacteria and little or minimal reduction of activity against gram negative bacteria.
• The addition at position two of nitrogen did show an improvement of the pharmacokinetic properties.
• They do have a link at positions 4 and 3 with the keto and carboxylic group which is an essential thing for binding to the gyrase DNA.
• The substitution at position number 5 by small groups like amino, nitro, halogens and alkyl groups could improve the tissue distribution and absorption. Though suggestions were raised that the substitution at position 5 could decrease the anti-bacterial properties.
• The substitution at position 6 by F, H, Br, Cl, nitro, methyl and Cyanide would actually increase the potency of anti-bacterial activity by means of improving the binding and penetration abilities.

Conclusion:

Flumequine:

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• It is a first generation fluoroquinolone
• Well absorbed orally and metabolized hepatically (glucuronide conjugates)
• Discontinued due to dangerous adverse effects such as hepatotoxicity
• Veterinary use only
• Black box warning
• Is used for UTI but discontinued in humans
• Mechanism of action is inhibition of DNA gyrase, less selective than third generation drugs and lower gram positive activity
• Was administered orally as tablets for human use but discontinued and mainly now as solutions for veterinary use
• Excreted in feces and urine

.

Balofloxacin:

• It is a third generation fluoroquinolone

• Well absorbed orally and minimal hepatic metabolism
• It is very useful because it has less adverse effects than other fluoroquinolones
• Human use
• No black box warning due to minimal side effects
• Mainly used for uncomplicated UTI
• Same mechanism of action of fluoroquinolones (Inhibition of DNA gyrase) more selective and improved gram positive activity due to 3rd generation properties
• Orally administered in the form of tablets
• Excreted in feces and urine

Reference:

Chemspider, Flumequine Available at: http://www.chemspider.com/Chemical-Structure.3257.html (Accessed: 12 April, 2015)

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FAO, Food and Agriculture Organization of The United States, Flumequine, Available at: http://www.fao.org/docrep/w8338e/w8338e0a.htm (Accessed: 12 April, 2015)

NCBI, Structure Activity relationships of The Fluoroquinolones, Anti microb Agents Chemother (1989) pages: 131-135 Available at: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC171443/

(Accessed: 12 April, 2015)

World Public Library, Flumequine Available at: http://www.netlibrary.net/articles/flumequine#Mode_of_action (Accessed: 12 April, 2015)

Medicine India. Balofloxacin Pharmacology. Available at: https://www.medicineindia.org/pharmacology-for-generic/2923/balofloxacin

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(Accessed: 13 April, 2015)

NCBI. Pharmacokinetics of the new fluoroquinolone balofloxacin in mice, rats, and dogs. (1995). Available at: http://www.ncbi.nlm.nih.gov/pubmed/7646579

(Accessed: 13 April, 2015)

WHO. Medical reference publication. (2005). PDF, Available at: http://www.netlibrary.net/eBooks/WPLBN0000173166.aspx

(Accessed: 13 April, 2015)

Drugs and Pharmacology. Balofloxacin. (2013). Available at: http://drugsandpharmacology.blogspot.com/2013/03/balofloxacin.html

(Accessed: 13 April, 2015)

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