Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C43H65FN6O10 |
Molecular Weight | 845.0088 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12[C@@H](C)C(=O)[C@H](C)C[C@@](C)(OC)[C@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@H](C)C(=O)[C@](C)(F)C(=O)O[C@H](CC)[C@@]1(C)OC(=O)N2CCCCN4C=C(N=N4)C5=CC=CC(N)=C5
InChI
InChIKey=IXXFZUPTQVDPPK-ZAWHAJPISA-N
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
DescriptionSources: http://melinta.com/publications/solithromycin/Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/history/solithera.html
https://www.ncbi.nlm.nih.gov/pubmed/23318809
Sources: http://melinta.com/publications/solithromycin/
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/history/solithera.html
https://www.ncbi.nlm.nih.gov/pubmed/23318809
Solithromycin is a highly potent next-generation macrolide, the first fluoroketolide, which has potent activity against most macrolide-resistant strains. In vitro and in vivo studies have shown potent activity against S. pneumoniae as well as an extended spectrum of activity against CA-MRSA, enterococci, Mycobacterium avium and in animal models of malaria. It is also active against atypical bacteria, such as Legionella, Chlamydophila, Chlamydia, Mycoplasmaand Ureaplasma and against gonococci and other organisms that cause genitourinary tract infections. It is 8-16 times more potent than azithromycin and is active against azithromycin-resistant strains. Its activity against resistant strains is driven by its ability to bind to three sites on the bacterial ribosome, compared to one or two for current macrolides. It binds to the large 50S subunit of the ribosome and inhibits protein biosynthesis. The binding to three ribosomal sites is expected to limit resistance development. On July 2016 Cempra Announces FDA Acceptance of IV and oral formulations of Solithera (solithromycin) New Drug Applications for in the treatment of community-acquired bacterial pneumonia.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23318809 |
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Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23318809 |
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Target ID: 50S subunit assembly, S. pneumoniae Sources: https://www.ncbi.nlm.nih.gov/pubmed/23318809 |
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Target ID: CHEMBL614430 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23796936 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Solithromycin inhibition of protein synthesis and ribosome biogenesis in Staphylococcus aureus, Streptococcus pneumoniae, and Haemophilus influenzae. | 2013 Apr |
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In-vitro activity of solithromycin against anaerobic bacteria from the normal intestinal microbiota. | 2016 Dec |
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In Vitro Activity of Solithromycin against Bordetella pertussis, an Emerging Respiratory Pathogen. | 2016 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01591447
A single oral dose of 1200 mg solithromycin
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23318809
For 50S subunit formation in S. pneumoniae, the IC50 for assembly inhibition was 15 ng/ml. Solithromycin was found to interfere with
50S ribosomal subunit formation in both methicillin-sensitive and methicillin-resistant strains of Staphylococcus aureus, with IC50s of 65 and 93 ng/ml, respectively
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NCI_THESAURUS |
C261
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WHO-ATC |
J01FA16
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760981-83-7
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WW-65
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DTXSID501028410
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DB09308
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100000169135
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9358
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CHEMBL1240704
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SOLITHROMYCIN
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9U1ETH79CK
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C152386
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25242512
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SUB182801
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ACTIVE MOIETY