ridinilazole   Click here for help

GtoPdb Ligand ID: 10853

Synonyms: SMT-19969 | SMT19969
PDB Ligand
Compound class: Synthetic organic
Comment: Ridinilazole (SMT19969) is an oral small molecule antibacterial that was developed to treat Clostridioides difficile infection. It exhibited potent bactericidal activity against all strains of C. difficile tested in vitro, and in in vivo models [1-4,7].

ridinilazole is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 83.14
Molecular weight 388.14
XLogP 3.95
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES n1ccc(cc1)c1nc2c([nH]1)cc(cc2)c1ccc2c(c1)[nH]c(n2)c1ccncc1
Isomeric SMILES n1ccc(cc1)c1nc2c([nH]1)cc(cc2)c1ccc2c(c1)[nH]c(n2)c1ccncc1
InChI InChI=1S/C24H16N6/c1-3-19-21(29-23(27-19)15-5-9-25-10-6-15)13-17(1)18-2-4-20-22(14-18)30-24(28-20)16-7-11-26-12-8-16/h1-14H,(H,27,29)(H,28,30)
InChI Key UHQFBTAJFNVZIV-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Baines SD, Crowther GS, Freeman J, Todhunter S, Vickers R, Wilcox MH. (2015)
SMT19969 as a treatment for Clostridium difficile infection: an assessment of antimicrobial activity using conventional susceptibility testing and an in vitro gut model.
J Antimicrob Chemother, 70 (1): 182-9. [PMID:25190720]
2. Corbett D, Wise A, Birchall S, Warn P, Baines SD, Crowther G, Freeman J, Chilton CH, Vernon J, Wilcox MH et al.. (2015)
In vitro susceptibility of Clostridium difficile to SMT19969 and comparators, as well as the killing kinetics and post-antibiotic effects of SMT19969 and comparators against C. difficile.
J Antimicrob Chemother, 70 (6): 1751-6. [PMID:25652750]
3. Goldstein EJ, Citron DM, Tyrrell KL, Merriam CV. (2013)
Comparative in vitro activities of SMT19969, a new antimicrobial agent, against Clostridium difficile and 350 gram-positive and gram-negative aerobic and anaerobic intestinal flora isolates.
Antimicrob Agents Chemother, 57 (10): 4872-6. [PMID:23877700]
4. Sattar A, Thommes P, Payne L, Warn P, Vickers RJ. (2015)
SMT19969 for Clostridium difficile infection (CDI): in vivo efficacy compared with fidaxomicin and vancomycin in the hamster model of CDI.
J Antimicrob Chemother, 70 (6): 1757-62. [PMID:25652749]
5. Snydman DR, McDermott LA, Thorpe CM, Chang J, Wick J, Walk ST, Vickers RJ. (2018)
Antimicrobial susceptibility and ribotypes of Clostridium difficile isolates from a Phase 2 clinical trial of ridinilazole (SMT19969) and vancomycin.
J Antimicrob Chemother, 73 (8): 2078-2084. [PMID:29718329]
6. Vickers RJ, Tillotson GS, Nathan R, Hazan S, Pullman J, Lucasti C, Deck K, Yacyshyn B, Maliakkal B, Pesant Y et al.. (2017)
Efficacy and safety of ridinilazole compared with vancomycin for the treatment of Clostridium difficile infection: a phase 2, randomised, double-blind, active-controlled, non-inferiority study.
Lancet Infect Dis, 17 (7): 735-744. [PMID:28461207]
7. Weiss W, Pulse M, Vickers R. (2014)
In vivo assessment of SMT19969 in a hamster model of clostridium difficile infection.
Antimicrob Agents Chemother, 58 (10): 5714-8. [PMID:25022586]