tetrodotoxin   Click here for help

GtoPdb Ligand ID: 2616

Synonyms: TTX
Compound class: Natural product
Comment: Tetrodotoxin is a potent neurotoxin found in certain fish and other aquatic animals, although it is actually produced in symbiotic bacteria hosted in these creatures.
There is some ambiguity in the literature and on other databases as to the exact stereochemistry of tetrodotoxin. Our structure matches that on ChEBI and the PubChem entry linked to above, while the compound is also represented by the alternative isomer in CHEMBL507974 and CID 11174599.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 8
Rotatable bonds 1
Topological polar surface area 190.25
Molecular weight 319.1
XLogP -3.58
No. Lipinski's rules broken 2
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Canonical SMILES OCC1(O)C2OC3(OC1C1C(C2O)(C3O)NC(=NC1O)N)O
Isomeric SMILES OC[C@@]1(O)[C@H]2O[C@]3(O[C@@H]1[C@H]1[C@@]([C@H]2O)([C@@H]3O)NC(=N[C@@H]1O)N)O
InChI InChI=1S/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3+,4-,5+,6-,7+,9+,10-,11+/m1/s1
No information available.
Summary of Clinical Use Click here for help
Subcutaneous tetrodotoxin has been evaluated in a Phase 3 clinical trial for its capacity to alleviate moderate to severe inadequately controlled cancer-related pain (NCT00725114).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Mechanistically, tetrodotoxin blocks voltage-gated sodium channels to prevent the rising phase of the action potential. Tetrodotoxin poisoning causes loss of sensation, paralysis of voluntary muscles including the diaphragm and intercostal muscles which compromises respiration. Tetrodotoxin poisoning is serious but not always fatal.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00725114 Safety & Efficacy Study of Subcutaneous Tetrodotoxin for Moderate to Severe Inadequately Controlled Cancer-related Pain Phase 3 Interventional Wex Pharmaceuticals Inc.