THC Science

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 ;
PubChem CID	71260;
ChemSpider	64388 ;
UNII	56C9DTE69V;
KEGG	D07242 ;
ChEBI	CHEBI:131719 ;
ChEMBL	ChEMBL2106403 ;
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 ; Key:XOEUHCONYHZURQ-HNUBZJOYSA-N ;
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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[edit]

^ 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.

[pmid3487389-1] 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.

[2] 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.

[1]

[2]

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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
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