otenaproxesul   Click here for help

GtoPdb Ligand ID: 9534

Synonyms: ATB 346 | ATB-346 | ATB-346, (S)- | ATB346
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Otenaproxesul (ATB-346) is a novel, orally administered, gastrointestinal-sparing hydrogen sulfide (H2S)-releasing analgesic and anti-inflammatory drug in clinical trials for osteoarthritis [8]. Structurally it comprises an H2S-releasing moiety covalently linked to a NSAID (naproxen). H2S-releasing NSAIDs are in development for their potential analgesic, anti-inflammatory, cytoprotective and chemopreventative properties [2-3,5-6,9-10].
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 2
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 93.64
Molecular weight 365.11
XLogP 4.19
No. Lipinski's rules broken 0
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 COc1ccc2c(c1)ccc(c2)C(C(=O)Oc1ccc(cc1)C(=S)N)C
Isomeric SMILES COc1ccc2c(c1)ccc(c2)[C@@H](C(=O)Oc1ccc(cc1)C(=S)N)C
InChI InChI=1S/C21H19NO3S/c1-13(21(23)25-18-8-5-14(6-9-18)20(22)26)15-3-4-17-12-19(24-2)10-7-16(17)11-15/h3-13H,1-2H3,(H2,22,26)/t13-/m0/s1
InChI Key YCNMAPLPQYQJFC-ZDUSSCGKSA-N
Bioactivity Comments
ATB-346 is a potent inhibitor of cyclooxygenase (COX) isozymes. ATB-346 mechanism of action is mediated in part by the release of H2S, hypothesized to be via desulfuration of its 4-hydroxy thiobenzamide moiety. The GI-sparing nature of this drug is evidenced by exposure not causing significant GI injury in rodents, dogs and humans at high doses, or in animals with impaired mucosal defense [1,4,7-8].