Trovafloxacin , CAS No.147059-72-1

CAS: 147059-72-1 Cat. No.: T650781 Molecular Weight: 416.4 PubChem CID: 62959

Synonyms

Trovafloxacin | WVPSKSLAZQPAKQ-CDMJZVDBSA-N | MFCD00871697 | 1,8-Naphthyridine-3-carboxylic acid, 7-(1.alpha.,5.alpha.,6.alpha.)-6-amino-3-azabicyclo3.1.0hex-3-yl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo- | DB00685 | TROVAFLOXACIN [VANDF] | 7-[(1

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Trovafloxacin is a broad-spectrum quinolone antibiotic with potent activity against Gram-positive , Gram-negative and anaerobic organisms . Trovafloxacin blocks the DNA gyrase and topoisomerase IV activity. Trovafloxacin is also a potent, selective and orally active pannexin 1 channel (PANX1) inhibitor with an IC 50 of 4 μM for PANX1 inward current. Trovafloxacin does not inhibit connexin 43 gap junction or PANX2. Trovafloxacin leads to dysregulated fragmentation of apoptotic cells by inhibiting PANX1

In Vitro

Trovafloxacin (20 µM; 24 hours; HepG2 cells) and tumor necrosis factor (TNF; 4 ng/mL) incubation induces apoptosis and increases leakage of lactate dehydrogenase (LDH) in HepG2 cells. Trovafloxacin (20 µM; 24 hours; HepG2 cells) and TNF (4 ng/mL) incubation increases expression of early NF-κB-related factors A20 and IκBα. Trovafloxacin prolongs TNF-induced activation of MAPKs and IKKα/β activation in HepG2. Trovafloxacin is a potent inhibitor of TO-PRO-3 uptake by apoptotic cells. Trovafloxacin also inhibits ATP release from apoptotic cells. Trovafloxacin does not inhibit caspase 3/7 activation, or caspase-mediated PANX1 cleavage during apoptosis. Trovafloxacin is equally active against both penicillin-susceptible and -resistant pneumococci, with MICs of 0.06-0.25 mg/mL reported for more than 700 isolates. The MICs of Trovafloxacin at which 90% of isolates are inhibited for 55 isolates of pneumococci is 0.125 μg/mL. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Apoptosis AnalysisCell Line: HepG2 cells Concentration: 20 µM Incubation Time: 24 hours Result: Showed a gradual increase of Annexin V-staining and an increased leakage of lactate dehydrogenase (LDH) at 24 h. RT-PCRCell Line: HepG2 cells Concentration: 20 µM Incubation Time: 24 hours Result: Caused a higher increase in the transcription of A20 and IκBα in HepG2 cells.

In Vivo

Trovafloxacin (150 mg/kg; oral administration; male C57BL/6 J mice) treatment disrupts TNF-induced p65 nuclear translocation. Trovafloxacin treatment increases expression of early NF-κB-related factors A20 and IκBα . Trovafloxacin, when administered in combination with lipopolysaccharide (LPS) or TNF to mice induces severe liver toxicity associated with vast apoptotic areas in the liver, increased serum levels of alanine amino transferases (ALT) and pro-inflammatory cytokines . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male C57BL/6 J mice (9-11-week-old) injected with recombinant murine TNF ion Dosage: 150 mg/kg Administration: Oral administration Result: Showed a greater number of cells with increased nuclear/cytoplasmic p65 ratio in liver.

Form:Solid

IC50& Target:Quinolone

Specifications

Synonyms

Trovafloxacin | WVPSKSLAZQPAKQ-CDMJZVDBSA-N | MFCD00871697 | 1, 8-Naphthyridine-3-carboxylic acid, 7-(1.alpha., 5.alpha., 6.alpha.)-6-amino-3-azabicyclo3.1.0hex-3-yl-1-(2, 4-difluorophenyl)-6-fluoro-1, 4-dihydro-4-oxo- | DB00685 | TROVAFLOXACIN [VANDF] | 7-[(1

Biochemical and Physiological Mechanisms

Trovafloxacin is a broad-spectrum quinolone antibiotic with potent activity against Gram-positive , Gram-negative and anaerobic organisms . Trovafloxacin blocks the DNA gyrase and topoisomerase IV activity. Trovafloxacin is also a potent, selective and or

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C1C2C(C2N)CN1C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F
• IUPAC Name: 7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
• InChIKey: WVPSKSLAZQPAKQ-SOSAQKQKSA-N
• INCHI: 1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16?
• Isomeric SMILES: C1[C@@H]2[C@@H](C2N)CN1C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F
• PubChem CID: 62959
• Molecular Weight: 416.4

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazanaphthalenes
      • Subclass Naphthyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazanaphthalenes
• Subclass: Naphthyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthyridine carboxylic acids and derivatives
• Alternative Parents: Fluoroquinolones Pyridinecarboxylic acids Dialkylarylamines Aminopiperidines Aminopyridines and derivatives Fluorobenzenes Aryl fluorides Imidolactams Vinylogous amides Pyrrolidines Heteroaromatic compounds Amino acids Monocarboxylic acids and derivatives Azacyclic compounds Carboxylic acids Hydrocarbon derivatives Monoalkylamines Organic oxides Organofluorides Organooxygen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Naphthyridine carboxylic acid - Fluoroquinolone - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Dialkylarylamine - 4-aminopiperidine - Aminopyridine - Halobenzene - Fluorobenzene - Aryl fluoride - Piperidine - Aryl halide - Monocyclic benzene moiety - Pyridine - Imidolactam - Benzenoid - Pyrrolidine - Heteroaromatic compound - Vinylogous amide - Amino acid - Amino acid or derivatives - Azacycle - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organonitrogen compound - Organooxygen compound - Primary amine - Organic oxygen compound - Organic nitrogen compound - Amine - Hydrocarbon derivative - Organic oxide - Primary aliphatic amine - Organopnictogen compound - Organofluoride - Organohalogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. These are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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INSR Tclin Insulin receptor (5558 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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RARA Tclin Retinoic acid receptor alpha (1324 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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CALCR Tclin Calcitonin receptor (2215 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

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Associated Targets(non-human)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Mc4r Melanocortin receptor 4 (1205 Activities)

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Ltc4s Leukotriene C4 synthase (1 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

Discover Target: Sigmar1

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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Hdac6 Histone deacetylase 6 (222 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Streptococcus pneumoniae (31063 Activities)

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Enterococcus (1748 Activities)

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Plasmodium yoelii yoelii (73 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella (302 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Bacteroides fragilis (1445 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Moraxella catarrhalis (3334 Activities)

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Escherichia coli (133304 Activities)

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Haemophilus influenzae (8812 Activities)

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Streptococcus pyogenes (16140 Activities)

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Enterococcus faecium (13803 Activities)

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Clostridium perfringens (1165 Activities)

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Listeria monocytogenes (2626 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Enterococcus faecalis (29875 Activities)

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Plasmodium falciparum (966862 Activities)

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Toxoplasma gondii (4585 Activities)

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Rattus norvegicus (775804 Activities)

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Streptococcus mitis (390 Activities)

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Staphylococcus sp. (496 Activities)

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V79-4 (87 Activities)

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NIH3T3 (5395 Activities)

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Streptococcus sp. 'group B' (533 Activities)

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Plasma (328 Activities)

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Coxiella burnetii (223 Activities)

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Glra2 Glycine receptor (1745 Activities)

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MC3T3-E1 (421 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 10 mg/mL (24.02 mM; ultrasonic and adjust pH to 4 with HCl)
• Molecular Weight: 416.400 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 416.11 Da
• Monoisotopic Mass: 416.11 Da
• Topological Polar Surface Area: 99.800 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 770.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Shiyi Tan, Yun Yang, Yu-Han Cai, Yuepu Pu, Zhongze Gu, Juan Zhang.  (2025)  Integrative analysis of levofloxacin-induced liver injury: Insights from pharmacovigilance, human liver organoids, and extracellular vesicle proteomics.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:40976438] [10.1016/j.taap.2025.117576]