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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
Structure of SOLITHROMYCIN

SMILES

CC[C@H]1OC(=O)[C@@](C)(F)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@H]3N(CCCCN4C=C(N=N4)C5=CC(N)=CC=C5)C(=O)O[C@]13C)OC

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

HIDE SMILES / InChI

Molecular Formula C43H65FN6O10
Molecular Weight 845.0088
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Curative
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
A single oral dose of 1200 mg solithromycin
Route of Administration: Oral
In Vitro Use Guide
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
Substance Class Chemical
Record UNII
9U1ETH79CK
Record Status Validated (UNII)
Record Version