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P0106

Sigma-Aldrich

Pefloxacin mesylate dihydrate

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Synonym(s):
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
Linear Formula:
C17H20FN3O3 • CH4O3S • 2H2O
CAS Number:
149676-40-4
Molecular Weight:
465.49
EC Number:
274-613-9
MDL number:
MFCD01685696
UNSPSC Code:
51101500
PubChem Substance ID:
329820015
NACRES:
NA.76

form

powder

Quality Level

100

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

2-8°C

SMILES string

O.O.CS(O)(=O)=O.CCN1C=C(C(O)=O)C(=O)c2cc(F)c(cc12)N3CCN(C)CC3

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

InChI key

LEULAXMUNMRLPW-UHFFFAOYSA-N

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General description

Chemical structure: fluoroquinolone

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 rodents. It′s cytotoxicity and uptake have been studied in primary cultures of rat hepatocytes.

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M A Simonin et al.
Antimicrobial agents and chemotherapy, 44(4), 867-872 (2000-03-18)
Despite a relatively low incidence of serious side effects, fluoroquinolones and the fluoroquinolone pefloxacin have been reported to occasionally promote tendinopathy that might result in the complication of spontaneous rupture of tendons. In the present study, we investigated in rodents
P Nordmann et al.
The Journal of antimicrobial chemotherapy, 24(3), 355-363 (1989-09-01)
The cytotoxicity and the uptake of three 4-quinolones--pefloxacin, ciprofloxacin, and ofloxacin--were investigated in primary cultures of rat hepatocytes. As assessed by intracellular enzyme release in culture media, pefloxacin at concentration 400 mg/l and ciprofloxacin at 200 mg/l were found to

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