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MedKoo Cat#: 414711 | Name: Flurithromycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Flurithromycin is a fluorinated semisynthetic macrolide antibiotic derived from erythromycin A, optimized for enhanced acid stability and tissue penetration. It binds the 50S ribosomal subunit at domain V of 23S rRNA, inhibiting peptidyl transferase and blocking protein elongation. Flurithromycin shows potent bioactivity against Gram-positive bacteria and select Gram-negative species, with improved MICs against erythromycin-resistant strains.

Chemical Structure

Flurithromycin
Flurithromycin
CAS#82664-20-8

Theoretical Analysis

MedKoo Cat#: 414711

Name: Flurithromycin

CAS#: 82664-20-8

Chemical Formula: C37H66FNO13

Exact Mass: 751.4518

Molecular Weight: 751.93

Elemental Analysis: C, 59.10; H, 8.85; F, 2.53; N, 1.86; O, 27.66

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Synonym
Flurithromycin; 8-Fluoroerythromycin; Fluritromicina; (8S)-8-Fluoroerythromycin A; Fluritromycinum;
IUPAC/Chemical Name
(3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-9-fluoro-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
InChi Key
XOEUHCONYHZURQ-HNUBZJOYSA-N
InChi Code
InChI=1S/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
SMILES Code
CC[C@H]1OC([C@@H]([C@H]([C@@H]([C@H]([C@](O)(C[C@](F)(C([C@@H]([C@H]([C@@]1(O)C)O)C)=O)C)C)O[C@@H]2O[C@@H](C[C@H](N(C)C)[C@H]2O)C)C)O[C@H]3C[C@@](OC)([C@H]([C@@H](O3)C)O)C)C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 751.93 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Fanos V, Mormile R, Benini D, Vecchini S, Cuzzolin L. Flurithromycin-induced acute interstitial nephritis. Pediatr Infect Dis J. 2000 Apr;19(4):366-7. doi: 10.1097/00006454-200004000-00027. PMID: 10783037. 2: Saverino D, Debbia EA, Pesce A, Lepore AM, Schito GC. Antibacterial profile of flurithromycin, a new macrolide. J Antimicrob Chemother. 1992 Sep;30(3):261-72. doi: 10.1093/jac/30.3.261. PMID: 1452490. 3: Blandino G, Lo Bue AM, Milazzo I, Nicolosi DV, Calì G, Cannavò V, Rossetti B. Comparison of systemic flurithromycin therapy and clinical procedures in the treatment of periodontal diseases. J Chemother. 2004 Apr;16(2):151-5. doi: 10.1179/joc.2004.16.2.151. PMID: 15216949. 4: Lo Bue AM, Blandino G, Milazzo I, Pasquantonio G, Speciale A, Nicoletti G. Antibacterial activity and post-antibiotic effect of flurithromycin compared with other macrolides and penicillins against periodontal pathogens. J Chemother. 2001 Jun;13(3):255-9. doi: 10.1179/joc.2001.13.3.255. PMID: 11450882. 5: Fera MT, Giannone M, Pallio S, Tortora A, Blandino G, Carbone M. Antimicrobial activity and postantibiotic effect of flurithromycin against Helicobacter pylori strains. Int J Antimicrob Agents. 2001 Feb;17(2):151-4. doi: 10.1016/s0924-8579(00)00315-0. PMID: 11165121. 6: Benoni G, Cuzzolin L, Leone R, Consolo U, Ferronato G, Bertrand C, Puchetti V, Fracasso ME. Pharmacokinetics and human tissue penetration of flurithromycin. Antimicrob Agents Chemother. 1988 Dec;32(12):1875-8. doi: 10.1128/AAC.32.12.1875. PMID: 3245699; PMCID: PMC176036. 7: Lepore AM, Bonardi G, Maggi GC. Influence of food on the absorption of flurithromycin in man. Int J Clin Pharmacol Res. 1988;8(4):253-7. PMID: 3182114. 8: Gialdroni Grassi G, Alesina R, Bersani C, Ferrara A, Fietta A, Peona V. In vitro activity of flurithromycin, a novel macrolide antibiotic. Chemioterapia. 1986 Jun;5(3):177-84. PMID: 3487389. 9: Kanfer I, Skinner MF, Walker RB. Analysis of macrolide antibiotics. J Chromatogr A. 1998 Jul 3;812(1-2):255-86. doi: 10.1016/s0021-9673(98)00276-3. PMID: 9691324. 10: Kirst HA. Semi-synthetic derivatives of erythromycin. Prog Med Chem. 1993;30:57-88. doi: 10.1016/s0079-6468(08)70375-8. PMID: 8303037.