Solithromycin

Solithromycin
Clinical data
Trade names	Solithera
Other names	CEM-101; OP-1068
Routes of; administration	Oral, intravenous
ATC code	J01FA16 (WHO) ;
Legal status
Legal status	Under FDA and EMA review for approval;
Identifiers
	IUPAC name (3aS,4R,7S,9R,10R,11R,13R,15R,15aR)-1-[4-[4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl]butyl]-4-ethyl-7-fluorooctahydro-11-methoxy-3a,7,9,11,13,15-hexamethyl-10-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-2H-Oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetrone;
CAS Number	760981-83-7 ;
DrugBank	DB09308 ;
ChemSpider	25056854 ;
UNII	9U1ETH79CK;
KEGG	D09965 ;
ChEMBL	ChEMBL1240704 ;
Chemical and physical data
Formula	C43H65FN6O10
Molar mass	845.023 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@](C(=O)O1)(C)F)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCn4cc(nn4)c5cccc(c5)N)C;
	InChI InChI=1S/C43H65FN6O10/c1-12-32-43(8)35(50(40(55)60-43)19-14-13-18-49-23-30(46-47-49)28-16-15-17-29(45)21-28)26(4)33(51)24(2)22-41(6,56-11)37(27(5)36(53)42(7,44)39(54)58-32)59-38-34(52)31(48(9)10)20-25(3)57-38/h15-17,21,23-27,31-32,34-35,37-38,52H,12-14,18-20,22,45H2,1-11H3/t24-,25-,26+,27+,31+,32-,34-,35-,37-,38+,41-,42+,43-/m1/s1 ; Key:IXXFZUPTQVDPPK-ZAWHAJPISA-N ;
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Solithromycin (trade name Solithera) is a ketolide antibiotic undergoing clinical development for the treatment of community-acquired pneumonia^[1] and other infections.^[2]

Solithromycin exhibits excellent in vitro activity against a broad spectrum of Gram-positive respiratory tract pathogens,^[3]^[4] including macrolide-resistant strains.^[5] Solithromycin has activity against most common respiratory Gram-positive and fastidious Gram-negative pathogens,^[6]^[7] and is being evaluated for its utility in treating gonorrhea.

^ Reinert RR (June 2004). "Clinical efficacy of ketolides in the treatment of respiratory tract infections". The Journal of Antimicrobial Chemotherapy. 53 (6): 918–927. doi:10.1093/jac/dkh169. PMID 15117934.
^ "Solithromycin". Cempra. Archived from the original on 18 March 2012.
^ Woosley LN, Castanheira M, Jones RN (May 2010). "CEM-101 activity against Gram-positive organisms". Antimicrobial Agents and Chemotherapy. 54 (5): 2182–2187. doi:10.1128/AAC.01662-09. PMC 2863667. PMID 20176910.
^ Farrell DJ, Sader HS, Castanheira M, Biedenbach DJ, Rhomberg PR, Jones RN (June 2010). "Antimicrobial characterisation of CEM-101 activity against respiratory tract pathogens, including multidrug-resistant pneumococcal serogroup 19A isolates". International Journal of Antimicrobial Agents. 35 (6): 537–543. doi:10.1016/j.ijantimicag.2010.01.026. PMID 20211548.
^ McGhee P, Clark C, Kosowska-Shick KM, Nagai K, Dewasse B, Beachel L, Appelbaum PC (January 2010). "In vitro activity of CEM-101 against Streptococcus pneumoniae and Streptococcus pyogenes with defined macrolide resistance mechanisms". Antimicrobial Agents and Chemotherapy. 54 (1): 230–238. doi:10.1128/AAC.01123-09. PMC 2798494. PMID 19884376.
^ Putnam SD, Castanheira M, Moet GJ, Farrell DJ, Jones RN (April 2010). "CEM-101, a novel fluoroketolide: antimicrobial activity against a diverse collection of Gram-positive and Gram-negative bacteria". Diagnostic Microbiology and Infectious Disease. 66 (4): 393–401. doi:10.1016/j.diagmicrobio.2009.10.013. PMID 20022192.
^ Putnam SD, Sader HS, Farrell DJ, Biedenbach DJ, Castanheira M (January 2011). "Antimicrobial characterisation of solithromycin (CEM-101), a novel fluoroketolide: activity against staphylococci and enterococci". International Journal of Antimicrobial Agents. 37 (1): 39–45. doi:10.1016/j.ijantimicag.2010.08.021. PMID 21075602.

[pmid15117934-1] Reinert RR (June 2004). "Clinical efficacy of ketolides in the treatment of respiratory tract infections". The Journal of Antimicrobial Chemotherapy. 53 (6): 918–927. doi:10.1093/jac/dkh169. PMID 15117934.

[2] "Solithromycin". Cempra. Archived from the original on 18 March 2012.

[pmid2017690-3] Woosley LN, Castanheira M, Jones RN (May 2010). "CEM-101 activity against Gram-positive organisms". Antimicrobial Agents and Chemotherapy. 54 (5): 2182–2187. doi:10.1128/AAC.01662-09. PMC 2863667. PMID 20176910.

[pmid20211548-4] Farrell DJ, Sader HS, Castanheira M, Biedenbach DJ, Rhomberg PR, Jones RN (June 2010). "Antimicrobial characterisation of CEM-101 activity against respiratory tract pathogens, including multidrug-resistant pneumococcal serogroup 19A isolates". International Journal of Antimicrobial Agents. 35 (6): 537–543. doi:10.1016/j.ijantimicag.2010.01.026. PMID 20211548.

[pmid19884376-5] McGhee P, Clark C, Kosowska-Shick KM, Nagai K, Dewasse B, Beachel L, Appelbaum PC (January 2010). "In vitro activity of CEM-101 against Streptococcus pneumoniae and Streptococcus pyogenes with defined macrolide resistance mechanisms". Antimicrobial Agents and Chemotherapy. 54 (1): 230–238. doi:10.1128/AAC.01123-09. PMC 2798494. PMID 19884376.

[6] Putnam SD, Castanheira M, Moet GJ, Farrell DJ, Jones RN (April 2010). "CEM-101, a novel fluoroketolide: antimicrobial activity against a diverse collection of Gram-positive and Gram-negative bacteria". Diagnostic Microbiology and Infectious Disease. 66 (4): 393–401. doi:10.1016/j.diagmicrobio.2009.10.013. PMID 20022192.

[7] Putnam SD, Sader HS, Farrell DJ, Biedenbach DJ, Castanheira M (January 2011). "Antimicrobial characterisation of solithromycin (CEM-101), a novel fluoroketolide: activity against staphylococci and enterococci". International Journal of Antimicrobial Agents. 37 (1): 39–45. doi:10.1016/j.ijantimicag.2010.08.021. PMID 21075602.

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