Flurithromycin

Flurithromycin
Clinical data

ATC code	J01FA14 (WHO)
Identifiers
IUPAC name (3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6- [(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy- 6-methyloxan-2-yl]oxy-14-ethyl-9-fluoro-7,12, 13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy- 4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9, 11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
CAS Number	82664-20-8^Y
PubChem CID	71260
ChemSpider	64388^Y
UNII	56C9DTE69V
KEGG	D07242^Y
ChEBI	CHEBI:131719^N
ChEMBL	ChEMBL2106403^N
CompTox Dashboard (EPA)	DTXSID40905085
ECHA InfoCard	100.126.548
Chemical and physical data
Formula	C₃₇H₆₆FNO₁₃
Molar mass	751.927 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C3O[C@H](CC)[C@](O)(C)[C@H](O)[C@H](C(=O)[C@](F)(C)C[C@](O)(C)[C@H](O[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O)[C@H]([C@H](O[C@@H]2O[C@H]([C@H](O)[C@](OC)(C2)C)C)[C@H]3C)C)C
InChI 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^Y Key:XOEUHCONYHZURQ-HNUBZJOYSA-N^Y
^NY (what is this?) (verify)

Flurithromycin is a second generation macrolide antibiotic. It is a fluorinated derivative of erythromycin A.^[1] It is a broad spectrum antibiotic with similar bactericidal action to erythromycin. Unlike erythromycin, flurithromycin is more tolerant of acidic environments, meaning more survives the digestion process, resulting in higher serum levels, and more efficacious elimination of susceptible bacteria, including staphylococcus aureus and streptococcus pyogenes.^[2]

References

^ Gialdroni Grassi G, Alesina R, Bersani C, Ferrara A, Fietta A, Peona V (June 1986). "In vitro activity of flurithromycin, a novel macrolide antibiotic". Chemioterapia. 5 (3): 177–184. PMID 3487389.
^ Kaneko T, Dougherty TJ, Magee TV (January 2007). "7.18 - Macrolide Antibiotics". In Taylor JB, Triggle DJ (eds.). Comprehensive Medicinal Chemistry II. Oxford: Elsevier. pp. 519–566. doi:10.1016/b0-08-045044-x/00219-4. ISBN 978-0-08-045044-5.

Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Boromycin Carbomycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Josamycin Kitasamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Tildipirosin Tilmicosin Troleandomycin Tulathromycin Tylosin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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This page was last edited on 12 October 2023, at 04:47

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References