1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid methanesulfonic acid dihydrate

• ChemBase ID: 120406
• Molecular Formular: C18H28FN3O8S
• Molecular Mass: 465.4936232
• Monoisotopic Mass: 465.15811409
• SMILES: c1(c(=O)c2c(n(c1)CC)cc(N1CCN(CC1)C)c(c2)F)C(=O)O.S(=O)(=O)(O)C.O.O
• Canonical SMILES: CS(=O)(=O)O.CCn1cc(C(=O)O)c(=O)c2c1cc(N1CCN(CC1)C)c(c2)F.O.O
• InChI: InChI=1S/C17H20FN3O3.CH4O3S.2H2O/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21;1-5(2,3)4;;/h8-10H,3-7H2,1-2H3,(H,23,24);1H3,(H,2,3,4);2*1H2
• InChIKey: LEULAXMUNMRLPW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid methanesulfonic acid dihydrate
• IUPAC Traditional name: methanesulfonic acid pefloxacin dihydrate; pefloxacin dihydrate mesylate
• Synonyms: 3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-, monomethanesulfonate, dihydrate; Pefloxacine monomethanesulfonate dihydrate; Pefloxacinium methanesulfonate dihydrate; Pefloxacin mesylate dihydrate; Pefloxacin Mesylate Dihydrate; 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid compound with methanesulfonic acid (1:1) dihydrate

Database IDs

• CAS Number: 149676-40-4
• EC Number: 274-613-9
• MDL Number: MFCD01685696
• PubChem SID: 162214759
• PubChem CID: 6917670

CALCULATED PROPERTIES

• Acid pKa: 5.6647615
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.72274345
• LogD (pH = 7.4): 0.16012752
• Log P: 0.8768126
• Molar Refractivity: 90.7715 cm^3
• Polarizability: 32.979492 Å^3
• Polar Surface Area: 64.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: VB2002200
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Topoisomerase

Product Information

• Salt Data: CH3SO3H, 2 H2O; Mesylate
• Linear Formula: C17H20FN3O3 • CH4O3S • 2H2O

DETAILS

Sigma Aldrich - P0106

Application
Pefloxacin is a synthetic broad-spectrum fluoroquinolone antibiotic that is effective against most gram-negative and gram-positive bacteria. It is used to treat gonococcal urethritis and for gram-negative-bacterial infections in the gastrointestinal system and the genitourinary tract. Pefloxacin mesylate dihydrate has been used to induce achilles tendon toxicity in rodents1. It′s cytotoxicity and uptake has been studied in primary cultures of rat hepatocytes2.
Biochem/physiol Actions
Pefloxacin inhibits the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase is thought to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV is thought to be the primary target in gram-positive organisms. The inhibition of the topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. Therefore, DNA replication and transcription is inhibited . Pefloxacin is an analog of norfloxacin.