7-[(1R,5S,6R)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid

• ChemBase ID: 154680
• Molecular Formular: C21H19F3N4O6S
• Molecular Mass: 512.4589696
• Monoisotopic Mass: 512.09774001
• SMILES: CS(=O)(=O)O.c1cc(c(cc1F)F)n1cc(c(=O)c2c1nc(c(c2)F)N1C[C@@H]2[C@H](C1)[C@H]2N)C(=O)O
• Canonical SMILES: CS(=O)(=O)O.N[C@@H]1[C@@H]2[C@H]1CN(C2)c1nc2c(cc1F)c(=O)c(cn2c1ccc(cc1F)F)C(=O)O
• InChI: InChI=1S/C20H15F3N4O3.CH4O3S/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;1-5(2,3)4/h1-4,7,10-11,16H,5-6,24H2,(H,29,30);1H3,(H,2,3,4)/t10-,11+,16+
• InChIKey: DYNZICQDCVYXFW-AHZSKCOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,5S,6R)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid; 7-[(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid
• IUPAC Traditional name: methanesulfonic acid; trovafloxacin; 7-[(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid
• Synonyms: CP 99219; CP 99219-27; Trovafloxacin Monomethanesulfonate; Trovan; Trovafloxacin Mesylate; 7-[(1α,5α,6α)-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-carboxylic Acid Methanesulfonate; (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-carboxylic acid methanesulfonate; CP-99219-27; Trovafloxacin methanesulfonate; Trovafloxacin mesylate

Database IDs

• CAS Number: 147059-75-4
• MDL Number: MFCD00913361
• PubChem SID: 162248818
• PubChem CID: 62960

CALCULATED PROPERTIES

• Acid pKa: 5.4131193
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.057143982
• LogD (pH = 7.4): 0.13973176
• Log P: 0.13645041
• Molar Refractivity: 101.0404 cm^3
• Polarizability: 36.818485 Å^3
• Polar Surface Area: 99.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL; Methanol (Sparingly)
• Apperance: White Solid; white to off-white powder
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: QN2791250
• European Hazard Symbols: Corrosive (C)
• UN Number: 1759
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 63-34
• Safety Statements: 26-36-45
• GHS Pictograms: GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H361
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• RID/ADR: UN 1759 8/PG 3
• Storage Temperature: room temp

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C20H15F3N4O3 · CH3SO3H

DETAILS

Sigma Aldrich - PZ0015

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Trovafloxacin mesylate is a broad spectrum antibiotic. Trovafloxacin mesylate blocks the activity of DNA gyrase and topoisomerase IV, enzymes essential in the repliction, transcription, and repair of bacterial DNA.

Toronto Research Chemicals - T893000

Fluorinated quinolone antibacterial. Trovafloxacin mesylate blocks the activity of DNA gyrase and topoisomerase IV, enzymes essential in the repliction, transcription, and repair of bacterial DNA.

REFERENCES

• Neu, H.C., et al.: Clin. Antimicrob. Agents Chemother., 38, 2615 (1994)
• Liguori, M.J., et al.: Hepatology, 41, 177 (1994)