Alatrofloxacin mesylate

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Alatrofloxacin Mesylate

Chemical Names: Alatrofloxacin mesylate; UNII-2IXX802851; 146961-77-5; Alatrofloxacin mesylate [USAN]; 157605-25-9; 2IXX802851
Molecular Formula: C27H29F3N6O8S
Molecular Weight: 654.618 g/mol
CAS No. 146961-76-4 (Alatrofloxacin );
157605-25-9 (Alatrofloxacin Mesylate);
Chemical Name (1α, 5α, 6α)-L-alanyl-N-[3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridine-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-L-alaninamide, monomethanesulfonate

Research Code:CP-116517-27; CP-116517,    Trade Name:Trovan I.V.®          MOA:Quinolone antibiotic            Indication:Life- or limb-threatening infections caused by susceptible strains          Status:Withdrawn    Company:Pfizer (Originator)

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.[1]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001

Alatrofloxacin mesylate was first approved by the U.S. Food and Drug Administration (FDA) on Dec 18, 1997. It was developed and marketed as Trovan I.V. ® by Pfizer in the US.

Alatrofloxacin mesylate is a fluoronaphthyridone related to the fluoroquinolones with in vitro activity against a wide range of gram-negative and gram-positive aerobic and anaerobic microorganisms. The bactericidal action of alatrofloxacin results from inhibition of DNA gyrase and topoisomerase IV. Trovan I.V.® is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below.

Trovan I.V.® is available as injection solution for intravenous use, containing 7.86 mg/ml of Alatrofloxacin mesylate. The recommended starting dose is 200 mg or 300 mg administered intravenously.

Alatrofloxacin mesylate was withdrawn from the U.S. market in 2001.

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Alatrofloxacin mesilate

    • Synonyms:CP 116517, CP 116517-27
    • ATC:J01MA
  • Use:antibiotic, prodrug of trovafloxacin
  • Chemical name:l-Alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-l-alaninamide monomethanesulfonate
  • Formula:C26H25F3N6O5 • CH4O3S
    • MW:654.62 g/mol
    • CAS-RN:146961-77-5



    • Formula:C26H25F3N6O5
    • MW:558.52 g/mol
    • CAS-RN:146961-76-4

    Substance Classes

    Synthesis Path

    Substances Referenced in Synthesis Path

    CAS-RN Formula Chemical Name CAS Index Name
    27317-69-7 C11H20N2O5 Ntert-butoxycarbonyl-l-alanyl-l-alanine L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-
    186772-86-1 C33H37F3N6O7 N-[(1,1-dimethylethoxy)carbonyl]-l-alanyl-N-[(1α,5α,6α)-3-[8-(2,4-difluorophenyl)-6-(ethoxycarbonyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-l-alaninamide L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-N-[(1α,5α,6α)-3-[8-(2,4-difluorophenyl)-6-(ethoxycarbonyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-
    171176-56-0 C22H19F3N4O3 ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 1,8-Naphthyridine-3-carboxylic acid, 7-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-, ethyl ester, (1α,5α,6α)-
    134575-66-9 C27H27F3N4O5 ethyl (1α,5α,6α)-1-(2,4-difluorophenyl)-7-[6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 1,8-Naphthyridine-3-carboxylic acid, 1-(2,4-difluorophenyl)-7-[6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-4-oxo-, ethyl ester, (1α,5α,6α)-
    75-75-2 CH4O3S methanesulfonic acid Methanesulfonic acid

    Trade Names

    Country Trade Name Vendor Annotation
    D TROVAN Pfizer wfm
    F Turvel Pfizer wfm
    GB Turvel Pfizer wfm
    I Turvel Pfizer wfm
    USA Trovan Pfizer wfm

    (wfm = withdrawn from market)


    • vial 200 mg/40 ml, 300 mg/60 ml (5 mg/ml) (as mesilate)


      • US 5 164 402 (Pfizer; 17.11.1992; appl. 4.2.1991; WO-prior. 16.8.1989).
      • US 5 229 396 (Pfizer; 20.7.1993; appl. 24.7.1992).
      • WO 9 700 268 (Pfizer; appl. 27.3.1996; USA-prior. 15.6.1995).
      • US 5 763 454 (Pfizer; 9.6.1998; appl. 21.5.1997; WO-prior. 6.6.1995).
    • polymorphs:

      • US 6 080 756 (Pfizer; 27.6.2000; appl. 30.1.1998; WO-prior. 5.7.1996).

    “Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)” (PDF). Food and Drug Administration. Retrieved 29 August 2014.

    Clinical data
    AHFS/ Micromedex Detailed Consumer Information
    MedlinePlus a605016
    • US: C (Risk not ruled out)
    Routes of
    ATC code
    • none
    Legal status
    Legal status
    • Withdrawn
    Pharmacokinetic data
    Bioavailability N/A
    Protein binding 76% (trovafloxacin)
    Metabolism Quickly hydrolyzed to trovafloxacin
    Elimination half-life 9 to 12 hours (trovafloxacin)
    Excretion Fecal and renal(trovafloxacin)
    CAS Number
    Chemical and physical data
    Formula C26H25F3N6O5
    Molar mass 558.509 g/mol
    3D model (JSmol)


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