Last update Nov. 20, 2020

(±)-7-[3-(Aminomethyl)-4-oxo-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid 74-(Z)-(O-methyloxime) methanesulfonate

Compatible

Safe substance and/or breastfeeding is the best option.

Fluoroquinolone antibacterial with actions and uses similar to those of ciprofloxacin.
Oral administration once daily.

It is excreted in small amount into breast milk (Sagirli 2015).

Structurally similar Quinolone-related medication has been used in neonates and infants without known side effects (Newby 2017, Dutta 2006, Belet 2004, Drossou 2004, van den Oever 1998, Gürpinar 1997). There are excreted tiny amounts into breast milk and absorption through the child’s gut may be interfered by calcium in the milk (Fleiss 1992, Neuvonen 1991).

Several experts consider the use of this medication probably safe during breastfeeding (Briggs 2017, Hale 2017 p 424).

Until there is more published data on this drug in relation to breastfeeding, safer known alternatives with a safer pharmacokinetic profile for breastfeeding may be preferable, especially in the neonatal period and in case of prematurity.

Should it be prescribed to a nursing mother Norfloxacine, Ofloxacine and Ciprofloxacine are to be chosen since they have shown a lowest excretion into the milk (Butler 2014).

The possibility of transient gastroenteritis due to alteration of the intestinal flora in infants whose mothers take antibiotics should be taken into account (Briggs 2017, Ito 1993).

Unreasonably prolonged or repetitive use of antibiotics is harmful to health.
Due to the publication of reports of serious or potentially serious side effects in patients treated with fluoroquinolones, several health authorities propose restricting their indiscriminate outpatient use and reserving them for certain serious diseases (EMA 2018, FDA 2016).

Alternatives

  • Ciprofloxacin (Safe substance and/or breastfeeding is the best option.)
  • Norfloxacin (Safe substance and/or breastfeeding is the best option.)
  • Ofloxacin (Safe substance and/or breastfeeding is the best option.)

Suggestions made at e-lactancia are done by APILAM team of health professionals, and are based on updated scientific publications. It is not intended to replace the relationship you have with your doctor but to compound it. The pharmaceutical industry contraindicates breastfeeding, mistakenly and without scientific reasons, in most of the drug data sheets.

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Other names

(±)-7-[3-(Aminomethyl)-4-oxo-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid 74-(Z)-(O-methyloxime) methanesulfonate is Gemifloxacino mesilato in Chemical name.

Is written in other languages:

Group

(±)-7-[3-(Aminomethyl)-4-oxo-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid 74-(Z)-(O-methyloxime) methanesulfonate belongs to this group or family:

Tradenames

Main tradenames from several countries containing (±)-7-[3-(Aminomethyl)-4-oxo-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid 74-(Z)-(O-methyloxime) methanesulfonate in its composition:

Pharmacokinetics

Variable Value Unit
Oral Bioavail. 71 %
Molecular weight 486 daltons
Protein Binding 60 - 70 %
VD 4.2 (1.7 - 12.1) l/Kg
pKa 5.53 -
Tmax 0.5 - 2 hours
T½ 7 ± 2 (4 - 12) hours
Theoretical Dose 0.015 - 0.37 mg/Kg/d
Relative Dose 0.32 - 8.1 %

References

  1. EMA-PRAC. Fluoroquinolone and quinolone antibiotics: PRAC recommends restrictions on use. Pharmacovigilance Risk Assessment Committee. 2018 Full text (link to original source) Full text (in our servers)
  2. EMA. Resumen de la audiencia pública de la EMA sobre antibióticos quinolonas y fluoroquinolonas. 2018 Full text (link to original source) Full text (in our servers)
  3. Hale TW, Rowe HE. Medications & Mothers' Milk. A Manual of Lactation Pharmacology. Springer Publishing Company. 2017
  4. Newby BD, Timberlake KE, Lepp LM, Mihic T, Dersch-Mills DA. Levofloxacin Use in the Neonate: A Case Series. J Pediatr Pharmacol Ther. 2017 Abstract
  5. FDA. La FDA actualiza las advertencias para los antibióticos conocidos como fluoroquinolonas. Comunicado de Prensa. 2016 Full text (link to original source)
  6. FDA. FDA updates warnings for fluoroquinolone antibiotics. News Release. 2016 Full text (link to original source) Full text (in our servers)
  7. Sagirli O, Demirci S, Önal A. A very simple high-performance liquid chromatographic method with fluorescence detection for the determination of gemifloxacin in human breast milk. Luminescence. 2015 Abstract
  8. Briggs GG, Freeman RK, Towers CV, Forinash AB. Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. Wolters Kluwer Health. Tenth edition (acces on line) 2015
  9. FDA (Oscient). Gemifloxacin. Drug Summary. 2008 Full text (in our servers)
  10. Dutta S, Chowdhary G, Kumar P, Mukhopadhay K, Narang A. Ciprofloxacin administration to very low birth weight babies has no effect on linear growth in infancy. J Trop Pediatr. 2006 Abstract
  11. Drossou-Agakidou V, Roilides E, Papakyriakidou-Koliouska P, Agakidis C, Nikolaides N, Sarafidis K, Kremenopoulos G. Use of ciprofloxacin in neonatal sepsis: lack of adverse effects up to one year. Pediatr Infect Dis J. 2004 Abstract
  12. Belet N, Haciömeroğlu P, Küçüködük S. Ciprofloxacin treatment in newborns with multi-drug-resistant nosocomial Pseudomonas infections. Biol Neonate. 2004 Abstract
  13. van den Oever HL, Versteegh FG, Thewessen EA, van den Anker JN, Mouton JW, Neijens HJ. Ciprofloxacin in preterm neonates: case report and review of the literature. Eur J Pediatr. 1998 Abstract
  14. Gürpinar AN, Balkan E, Kiliç N, Kiriştioğlu I, Doğruyol H. The effects of a fluoroquinolone on the growth and development of infants. J Int Med Res. 1997 Abstract
  15. Fleiss PM. The effect of maternal medications on breastfeeding infants. J Hum Lact. 1992 Abstract
  16. Neuvonen PJ, Kivistö KT, Lehto P. Interference of dairy products with the absorption of ciprofloxacin. Clin Pharmacol Ther. 1991 Abstract

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