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Pefloxacin

Pefloxacin structure

CAS No:
70458-92-3
Formula:
C17H20FN3O3
Chemical Name:
Pefloxacin
Synonyms:
3-Quinolinecarboxylic acid,1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-;1-Ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;1584RB;Pefloxacine;Pefloxacin;AM 725;Peflacine;N′-Methylnorfloxacin;Abaktal;Abactal;1589RB;EU 5306;Pelox;Perti;Pefbid;Globacin;Perflacin;1-Ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid;408363-79-1
Categories:
Active Pharmaceutical Ingredients > Inhibitor Drugs

Description

ChEBI: A quinolone that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6 and 7 by ethyl, carboxy, fluorine, and 4-methylpiperazin-1-yl groups, respectively.

Solid

Pefloxacin is a quinolone that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6 and 7 by ethyl, carboxy, fluorine, and 4-methylpiperazin-1-yl groups, respectively. It has a role as an antiinfective agent, a DNA synthesis inhibitor and an antibacterial drug. It is a quinolone, a N-arylpiperazine, a N-alkylpiperazine, a quinolone antibiotic, a fluoroquinolone antibiotic and a monocarboxylic acid.|A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria.|Pefloxacin is a fluoroquinolone antibiotic with broad-spectrum antimicrobial activity. Pefloxacin inhibits the activity of microbial DNA gyrase and topoisomerase IV. This disrupts DNA replication and prevents cell division.

Pefloxacin Basic Attributes

Molecular Weight：

333.36

Exact Mass：

333.36

EC Number：

274-611-8

UNII：

2H52Z9F2Q5

DSSTox ID：

DTXSID3048493

NCI Thesaurus Code：

C728

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

64.1

XLogP3：

0.3

Appearance：

Solid

Density：

1.320±0.06 g/cm3(Predicted)

Melting Point：

271 °C (decomp)

Boiling Point：

529.1ºC at 760 mmHg

Flash Point：

273.8ºC

Refractive Index：

1.593

Water Solubility：

1.23e+00 g/L

Vapor Pressure：

5.05E-12mmHg at 25°C

Toxicity：

LD50 in mice (mg/kg): 225 i.v., 1000 orally; in rats (g/kg): 1.5 i.p., 2.5 orally (Goueffon)

Collision Cross Section：

188.8 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|194.2 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|178.17 Å² [M+H]+

Safety Information

Transport codes：

UN 3082

hazard class code：

R51/53

safety instructions：

S61

RTECS Number：

WM6250000

Marks：

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Adverse reactions include peripheral neuropathy, nervousness, agitation, anxiety, and phototoxic events (rash, itching, burning) due to sunlight exposure.

Protein Binding：

20-30%

Drug Information

Drug Indication：

For the treatment of uncomplicated gonococcal urethritis in males and for gram-negative-bacterial infections in the gastrointestinal system and the genitourinary tract.

Pharmacology：

Pefloxacin is a fluoroquinolone antibiotic. Flouroquinolones such as pefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.

MeSH：

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)

Absorption：

Well absorbed by the oral route.

Metabolism/Metabolites：

Hepatic. Primary metabolites are pefloxacin N-oxide and norfloxacin.

Biological Half-Life：

8.6 hours

Mechanism of Action：

The bactericidal action of pefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.

MeSH Entry Terms：

2589 R.B.

Pefloxacin Use and Manufacturing

Methods of Manufacturing

Its synthesis can be obtained by norfloxacin as raw material and methylated. It can also be prepared from the intermediate boron chelate in norfloxacin. The boron chelate compound, acetonitrile, N-methylpiperazine and triethylamine are mixed, and then reacted at room temperature and then refluxed. The solvent was distilled off, water was added, and concentrated hydrochloric acid was adjusted to Ph=3 before refluxing. Add activated carbon to decolorize and filter. The filtrate was alkalized to Ph=11, and then activated carbon was decolorized, filtered, and neutralized with 30% acetic acid to Ph=6.7-7.2, overnight in the refrigerator. Filtration, washing with water and drying to obtain off-white pefloxacin, yield 82%, melting point 270-272℃. Pefloxacin is dissolved in absolute ethanol, and methanesulfonic acid is added dropwise at 60-70°C to react. After cooling to 15°C, the precipitated crystals were filtered and recrystallized with 10 times ethanol to obtain pefloxacin methanesulfonate with a yield of 88.5%. The boron chelate, N-methylpiperazine and triethylamine can also be refluxed together. After alkaline hydrolysis, acidify to Ph=7.2 to obtain pefloxacin; add it to the aqueous solution of methanesulfonic acid, and the crude product obtained from the reaction is recrystallized with 85% ethanol to obtain pefloxacin mesylate, yield 79.4 %, melting point 284℃.

Uses

antibacterial;DNA gyrase inhibitor

Computed Properties

Molecular Weight:333.36
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:333.14886967
Monoisotopic Mass:333.14886967
Topological Polar Surface Area:64.1
Heavy Atom Count:24
Complexity:545
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

1-Methylpiperazine

Triethylamine

Formaldehyde

Ethanol

Norfloxacin

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Pefloxacin Manufacturer/High quality/Best price/In stock

CAS No.: 70458-92-3

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Pefloxacin CAS 70458-92-3

CAS No.: 70458-92-3

Grade: Pharmaceutical Grade

Content: 99%

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