82664-20-8

Basic information

• Product Name: FLURITHROMYCIN
• Synonyms: (8s)-8-fluoroerythromycina;8-fluoro-erythromyci;8-fluoroerythromycin;antibioticp80206;cl-932;fluritromicina;p80206;FLURITHROMYCIN
• CAS NO: 82664-20-8
• Molecular Formula: C₃₇H₆₆FNO₁₃
• Molecular Weight: 751.92
• Product Categories: Carbohydrates & Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 82664-20-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 814.6°C at 760 mmHg
• Flash Point: 446.5°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 9.85E-31mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 12.94±0.70(Predicted)
• CAS DataBase Reference: FLURITHROMYCIN(CAS DataBase Reference)
• NIST Chemistry Reference: FLURITHROMYCIN(82664-20-8)
• EPA Substance Registry System: FLURITHROMYCIN(82664-20-8)

Safety Data

• Hazard Codes: F
• Statements: 10
• Safety Statements: 16
• Hazardous Substances Data: 82664-20-8(Hazardous Substances Data)

Usage

Uses

A fluorinated derivative of Erythromycin (E649950). A macrolide antibiotic.

Definition

ChEBI: An erythromycin derivative that is erythromycin A in which the hydrogen attached to the carbon at position 8 (alpha to the ketone carbonyl group) has been replaced by a fluorine. It has been used (generally as the corresponding monoethyl s ccinate ester) as an antibacterial drug.

Pharmaceutical Applications

A semisynthetic derivative of erythromycin A, supplied for oral administration. It is stable at acid pH due to the presence of the fluorine atom at C-8 of the erythronolide A ring.It is active against most streptococci (including Str. pneumoniae and Str. agalactiae; MIC50 0.03 mg/L), Mor. catarrhalis, N. gonorrhoeae (MIC50 0.04 mg/L), C. trachomatis (MIC 0.06– 0.125 mg/L), M. genitalium (MIC50 0.007 mg/L) and U. urealyticum (MIC50 0.03 mg/L). It has little or no activity against H. influenzae and M. hominis. Activity against anaerobes is similar to that of erythromycin A. It displays cross-resistance with erythromycin A.A single 500 mg oral dose achieved a mean peak plasma concentration of 1.2–2 mg/L after 1–2 h. The apparent elimination half-life was 8 h and the volume of distribution 5.5 L/ kg. With repeated doses (500 mg orally every 8 h for 10 doses), plasma concentrations were 0.72 mg/L immediately before and 0.67 mg/L at 4 h after the last dose. Absorption is not significantly affected by food. After administration of a single 375 mg tablet of flurithromycin ethylsuccinate, the mean serum levels at 0.5 h were 0.43 ± 0.35 mg/L. The mean peak serum concentration (1.41 ± 0.49 mg/L) was achieved at 1 h. At 8 and 12 h, the serum levels were 0.14 (± 0.05) and 0.04 (± 0.04) mg/L, respectively. The apparent elimination half-life is 3.94 (± 1.42) h. The apparent half-life in artificial gastric juice was about 40 min.It is generally well tolerated and has been used successfully for the treatment of lower respiratory tract infections. Availability is limited.

InChI:InChI=1/C37H66FNO13/c1-14-24-37(10,46)29(42)21(5)28(41)34(7,38)17-35(8,45)31(52-33-26(40)23(39(11)12)15-18(2)48-33)19(3)27(20(4)32(44)50-24)51-25-16-36(9,47-13)30(43)22(6)49-25/h18-27,29-31,33,40,42-43,45-46H,14-17H2,1-13H3/t18-,19+,20-,21+,22+,23+,24-,25+,26-,27+,29-,30+,31-,33+,34+,35-,36-,37-/m1/s1

Upstream product

• 140681-55-6 Selectfluor 
• 114-07-8 erythromycin 

Relevant articles and documents

Preparation of (8S)-8-fluoroerythromycins with N-F fluorinating agents

(8S)-8-fluoroerythromycins are prepared by reacting 8,9-anhydroerythromycin 6,9-hemiacetals or an N-oxide thereof with a carboxylic acid and an N-F fluorinating agent. The anhydro starting material may be prepared in situ from erythromycins or an N-oxide