solithromycin   Click here for help

GtoPdb Ligand ID: 10859

Synonyms: CEM-101 | CEM101 | compound 3 [PMID: 30258539] | OP-1068 | OP1068 | Solithera | T-4288 | T4288
PDB Ligand
Compound class: Synthetic organic
Comment: Solithromycin is a next-generation oral and intravenous fluoroketolide (macrolide) antibacterial that has activity against Gram-positive and Gram-negative bacteria [2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 15
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 197.87
Molecular weight 844.47
XLogP 3.4
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical 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@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)N2CCCCn1nnc(c1)c1cccc(c1)N)C)C)(C)OC
Isomeric 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@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)N2CCCCn1nnc(c1)c1cccc(c1)N)C)C)(C)OC
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
InChI Key IXXFZUPTQVDPPK-ZAWHAJPISA-N
References
1. Barrera CM, Mykietiuk A, Metev H, Nitu MF, Karimjee N, Doreski PA, Mitha I, Tanaseanu CM, Molina JM, Antonovsky Y et al.. (2016)
Efficacy and safety of oral solithromycin versus oral moxifloxacin for treatment of community-acquired bacterial pneumonia: a global, double-blind, multicentre, randomised, active-controlled, non-inferiority trial (SOLITAIRE-ORAL).
Lancet Infect Dis, 16 (4): 421-30. [PMID:26852726]
2. Buege MJ, Brown JE, Aitken SL. (2017)
Solithromycin: A novel ketolide antibiotic.
Am J Health Syst Pharm, 74 (12): 875-887. [PMID:28432048]
3. Chen MY, McNulty A, Avery A, Whiley D, Tabrizi SN, Hardy D, Das AF, Nenninger A, Fairley CK, Hocking JS et al.. (2019)
Solithromycin versus ceftriaxone plus azithromycin for the treatment of uncomplicated genital gonorrhoea (SOLITAIRE-U): a randomised phase 3 non-inferiority trial.
Lancet Infect Dis, 19 (8): 833-842. [PMID:31196813]
4. File Jr TM, Rewerska B, Vucinic-Mihailovic V, Gonong JRV, Das AF, Keedy K, Taylor D, Sheets A, Fernandes P, Oldach D et al.. (2016)
SOLITAIRE-IV: A Randomized, Double-Blind, Multicenter Study Comparing the Efficacy and Safety of Intravenous-to-Oral Solithromycin to Intravenous-to-Oral Moxifloxacin for Treatment of Community-Acquired Bacterial Pneumonia.
Clin Infect Dis, 63 (8): 1007-1016. [PMID:27448679]
5. Jin X, Daher SS, Lee M, Buttaro B, Andrade RB. (2018)
Ribosome-Templated Azide-Alkyne Cycloadditions Using Resistant Bacteria as Reaction Vessels: in Cellulo Click Chemistry.
ACS Med Chem Lett, 9 (9): 907-911. [PMID:30258539]
6. Wen J, Chen F, Zhao M, Wang X. (2019)
Solithromycin monotherapy for treatment of community-acquired bacterial pneumonia: A meta-analysis of randomised controlled trials.
Int J Clin Pract, 73 (5): e13333. [PMID:30810253]