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Florfenicol

Florfenicol structure

CAS No:
73231-34-2
Formula:
C12H14Cl2FNO4S
Chemical Name:
Florfenicol
Synonyms:
Acetamide,2,2-dichloro-N-[(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]-;Acetamide,2,2-dichloro-N-[1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]-,[R-(R*,S*)]-;2,2-Dichloro-N-[(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide;Sch 25298;Florfenicol;(-)-Florfenicol;Nuflor;Aquafen;Aquaflor;Floron;Flonicol;Topazone;Florgane;Selectan;76639-94-6;81588-76-3;173008-78-1
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

Florfenicol, a commonly used veterinary antibiotic, is currently indicated for the treatment of bovine respiratory disease, and also used in aquaculture for the control of enteric septicemia in catfish. Florfenicol can induce early embryonic death in eggs, with an LC50 of 1.07 μg/g.

Florfenicol is a carboxamide that is the N-dichloroacetyl derivative of (1R,2S)-2-amino-3-fluoro-1-[4-(methanesulfonyl)phenyl]propan-1-ol. A synthetic veterinary antibiotic that is used for treatment of bovine respiratory disease and foot rot; also used in aquaculture. It has a role as an antimicrobial agent. It is a sulfone, a secondary alcohol, an organofluorine compound, an organochlorine compound and a secondary carboxamide. It derives from a dichloroacetic acid.|Florfenicol is a fluorinated synthetic analog of thiamphenicol.

Florfenicol Basic Attributes

Molecular Weight：

358.21300

Exact Mass：

358.21

UNII：

9J97307Y1H

DSSTox ID：

DTXSID9045500

ATC Code：

QS02CA90|QS02CA91|QJ01BA99

HScode：

2930909090

Characteristics

PSA：

91.85000

XLogP3：

0.8

Appearance：

White Crystalline Powder

Density：

1.451 g/cm3

Melting Point：

153-154 °C

Boiling Point：

617.5ºC at 760 mmHg

Flash Point：

327.3ºC

Refractive Index：

1.548

Storage Conditions：

0-6ºC

Collision Cross Section：

170.7 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|174.1 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26-S36

Marks：

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H361 (93.02%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P260, P264, P270, P273, P281, P308+P313, P314, P391, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Treatment of acute otitis externa.|For the treatment of acute canine otitis externa or acute exacerbations of recurrent otitis caused by mixed infections of susceptible strains of bacteria sensitive to florfenicol (Staphylococcus pseudintermedius) and fungi sensitive to terbinafine (Malassezia pachydermatis).|For therapeutic treatment of bovine respiratory disease (BRD) associated with pyrexia due to Mannheimia haemolytica, Pasteurella multocida and Histophilus somni susceptible to florfenicol.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

3-fluorothiamphenicol

Florfenicol Use and Manufacturing

Methods of Manufacturing

In a 100 mL three-necked flask, 4 g (4R, 5R) _5_ dichloroacetamido)_4_(4-carbazyl)_1, 3, 2-dioxathiaxanthene-2, 2-dioxide ( IV_2) dissolved in 30mLl, 2-dichloroethane solvent, 6g of triethylamine hydrofluoric acid salt, heated to 70 C reflux reaction for 8h, TLC or HPLC monitoring reaction, after the reaction of the raw materials, cooled to room temperature. At 0 C, 5 mL of 2 mol 1 / L hydrochloric acid was added dropwise. After the completion of the dropwise addition, the reaction was carried out at 0 C for 2 h. After the reaction was completed, the solvent was evaporated under reduced pressure. EtOAc (EtOAc m. Solvent, crude by column chromatography (petroleum ether / ethyl acetate = 2:1, v / nu)The white solid was 1.4 g, and the HPLC purity was determined to be 99.6 %Collecting the solution of Compound B in the reaction kettle, The solvent was then distilled off.90 g of sodium acetate (1.10 mol, 0.4 eq) and360g of methanol was added to the reaction kettle, The reaction was carried out at 60 C for 60 minutes, and then the solvent was distilled off under reduced pressure. Add 7200 g of an aqueous solution of isopropanol (25%).The temperature is raised to 70-80 C to recrystallize, the temperature of the reaction liquid is lowered to 10 to 20 C, and the product compound C is obtained by suction filtration.After drying, 912 g was obtained, and the yield was 95%.

Uses

Fluorinated derivative of thiamphenicol. Inhibits bacterial protein synthesis by binding to ribosome 50S and 70S subunits.Antibacterial drugs. Veterinary antimicrobial agent for bacterial diseases of pigs, chickens and fish caused by sensitive bacteria, for bacterial diseases of pigs, chickens and fish caused by sensitive bacteria, especially for respiratory system infections and intestinal infections

Use Classification：

Veterinary drugs -> Osurnia -> EMA Drug Category|Corticosteroids and antiinfectives in combination -> Veterinary pharmacotherapeutic group|Veterinary drugs -> Neptra -> EMA Drug Category|Otologicals, Corticosteroids and antiinfectives in combination -> Veterinary pharmacotherapeutic group|Veterinary drugs -> Zeleris -> EMA Drug Category|Antibacterials for systemic use, Amphenicols, combinations -> Veterinary pharmacotherapeutic group|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Computed Properties

Molecular Weight:358.2
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:357.0004627
Monoisotopic Mass:357.0004627
Topological Polar Surface Area:91.8
Heavy Atom Count:21
Complexity:447
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

Make your Florfenicol purchase based on the price and market insights! ECHEMI provides professional market insights with prices for you to make a better choice. Learn more on Florfenicol prices .

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