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70458-92-3

Basic Information
CAS No.: 70458-92-3
Name: Pefloxacin
Article Data: 13
Molecular Structure:
Molecular Structure of 70458-92-3 (Pefloxacin)
Formula: C17H20FN3O3
Molecular Weight: 333.363
Synonyms: 1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;
EINECS: 274-611-8
Density: 1.32 g/cm3
Melting Point: 270-272° (dec)
Boiling Point: 529.1 °C at 760 mmHg
Flash Point: 273.8 °C
Hazard Symbols: N
Risk Codes: R51/53
PSA: 65.78000
LogP: 1.61340
Synthetic route
109-01-3

1-methyl-piperazine

68077-26-9

7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

A

70458-92-3

Pefloxacin

B

7-Chloro-1-ethyl-6-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
In water for 13h; Heating;A 90%
B n/a
In dimethylsulfoxide-d6 at 120 - 130℃;A 82 % Spectr.
B 18 % Spectr.
50-00-0

formaldehyd

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

70458-92-3

Pefloxacin

Conditions
ConditionsYield
With formic acid Heating;85%

4-(t-butyldimethylsilyl)-1-methyl piperazine

68077-26-9

7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

22206-57-1

tetra-n-butylammoniumfluoride trihydrate

70458-92-3

Pefloxacin

Conditions
ConditionsYield
In water; acetonitrile85%
109-01-3

1-methyl-piperazine

68077-26-9

7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

70458-92-3

Pefloxacin

Conditions
ConditionsYield
at 130 - 140℃; for 5h;68%
70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

74-88-4

methyl iodide

70458-92-3

Pefloxacin

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 80 - 90℃; for 2h;30%
109-01-3

1-methyl-piperazine

70032-25-6

6,7-difluoro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

70458-92-3

Pefloxacin

Conditions
ConditionsYield
Yield given. Multistep reaction;
In dimethyl sulfoxide at 40℃; Rate constant; or over the mixed anhydrides with BF3 or BBr3 (facilitate the aromatic substitution);
74-83-9

methyl bromide

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

70458-92-3

Pefloxacin

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 80 - 90℃; for 2h;
109-01-3

1-methyl-piperazine

C16H14BClFNO7

70458-92-3

Pefloxacin

Conditions
ConditionsYield
With sodium hydroxide 1.) DMSO, 110 deg C, 2 h; 2.) reflux, 1 h; Yield given;
367-21-5

3-chloro-4-fluorophenylamine

70458-92-3

Pefloxacin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 100 percent / 2 h / 120 - 130 °C
2: diphenyl ether / 1 h / Heating
3: 90 percent / K2CO3 / dimethylformamide / 10 h / 80 - 90 °C
4: 90 percent / 2N NaOH / 2 h / Heating
5: 66 percent / 5 h / 130 - 140 °C
6: 85 percent / 87percent HCOOH / Heating
View Scheme
Multi-step reaction with 6 steps
1: 100 percent / 2 h / 120 - 130 °C
2: diphenyl ether / 1 h / Heating
3: 90 percent / K2CO3 / dimethylformamide / 10 h / 80 - 90 °C
4: 90 percent / 2N NaOH / 2 h / Heating
5: 66 percent / 5 h / 130 - 140 °C
6: 30 percent / Et3N / dimethylformamide / 2 h / 80 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1: 100 percent / 2 h / 120 - 130 °C
2: diphenyl ether / 1 h / Heating
3: 90 percent / K2CO3 / dimethylformamide / 10 h / 80 - 90 °C
4: 90 percent / 2N NaOH / 2 h / Heating
5: 68 percent / 5 h / 130 - 140 °C
View Scheme
68077-26-9

7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

70458-92-3

Pefloxacin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 66 percent / 5 h / 130 - 140 °C
2: 85 percent / 87percent HCOOH / Heating
View Scheme
Multi-step reaction with 2 steps
1: 66 percent / 5 h / 130 - 140 °C
2: 30 percent / Et3N / dimethylformamide / 2 h / 80 - 90 °C
View Scheme
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110719-58-9
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Chemistry

Pefloxacin(70458-92-3) is a synthetic chemotherapeutic agent used to treat severe and life threatening bacterial infections. Pefloxacin is commonly referred to as a fluoroquinolone (or quinolone) drug and is a member of the fluoroquinolone class of antibacterials. It is an analog of norfloxacin. It is a synthetic fluoroquinolone, belonging to the 3rd generation of quinolones. Pefloxacin is extensively prescribed in France. Pefloxacin has not been approved for use in the United States.

There are no licensed uses for Pefloxacin(70458-92-3) in the United States, as the FDA has not approved this drug. The licensed use varies in other countries and is quite limited as Pefloxacin is to be considered a drug of last resort when all other antibiotics have failed. There appears to be eight common uses in the adult population and no approved uses in the pediatric population, as well as a variety of veterinary uses (as documented within the package inserts). Pefloxacin interacts with a number of other drugs, a number of herbal and natural supplements, and certain thyroid medications.
The molecular formula of Pefloxacin mesylate(70458-92-3) is C17H20FN3O3 and its formula weight is 465.49.
The chemical synonyms of Pefloxacin mesylate(70458-92-3) are RB-1589;PEFLOXACIN;PEFLOXACINE MESYLATE DIHYDRATE;PEFLOXACINE METHANSULFONATE DIHYDRATE;PEFLOXACIN MESYLATE DIHYDRATE;PEFLOXACIN METHANESULFONATE;PEFLOXACIN METHANE SULFONATE DIHYDRATE;PERFLOXACINE
The molecular structure of Pefloxacin mesylate(70458-92-3):

Uses

Pefloxacin has been increasingly used as a veterinary medicine to treat microbial infections.

Antibiotics such as Pefloxacin do not improve sinusitis symptoms.  When prescribed for Community Acquired Pneumonia, Chronic Bronchitis, and Acute Bacterial Sinusitis the use of the fluoroquinolone class offers no compelling advantages over established treatment  Nor does antibiotic treatment help sore throats. The use of antibiotics such as Pefloxacin to treat bronchitis is to be considered unnecessary and as such exposes the patient to an unacceptable risk of suffering a severe adverse reaction.  Antibiotics' futility against bronchitis had been confirmed in 2002.  Since Streptococci and Pneumococci show only intermediate susceptibility to pefloxacin, the drug should not be prescribed as 1st-line treatment in respiratory tract infections, when bacteriological examination has not been carried out.
Additionally Pefloxacin and other fluoroquinolones have no effect upon viral infections such as the common head cold.

Specification

Pefloxacin should only be administered as described within the Dosage Guidelines table found within the most current package insert. The status of the patient’s renal function and hepatic function must also be taken into consideration to avoid an accumulation that may lead to a fatal drug overdose. Pefloxacin is eliminated partially through renal excretion. However, the drug is also metabolized and partially cleared through the liver and the intestine. Modification of the dosage is recommended using the table found within the package insert for those with impaired liver or kidney function. (Particularly for patients with severe renal dysfunction.) However, since the drug is known to be partially excreted by the kidneys, the risk of toxic reactions to this drug may be greater in patients with impaired renal function.

Recommended Doseage: 400 mg p.o. BID or QD Injectable; Injection; Pefloxacin Mesylate Dihydrate 400 mg / 5 ml Tablet, Film-Coated; Oral; Pefloxacin Mesylate Dihydrate 400 mg Oral Tablets: 400 mg Twice daily Injection: Administer by slow I.V. at a dosage of 400 mg diluted in 100 or 250 ml of 5% isotonic solution (Over a period of 1 hr) Twice daily.