Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Tetrodotoxin
- DrugBank Accession Number
- DB05232
- Background
An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order tetraodontiformes, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction. Tetrodotoxin is being investigated by Wex Pharmaceuticals for the treatment of chronic and breakthrough pain in advanced cancer patients as well as for the treatment of opioid dependence.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Tetrodotoxin (DB05232)
- Weight
- Average: 319.268
Monoisotopic: 319.101564535 - Chemical Formula
- C11H17N3O8
- Synonyms
- Tetrodotoxin
Pharmacology
- Indication
For the treatment of chronic and breakthrough pain in advanced cancer patients as well as for the treatment of opioid dependence.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Tetrodotoxin binds to site 1 of the fast voltage-gated sodium channel located at the extracellular pore opening. The binding of any molecules to this site will temporarily disable the function of the ion channel. Saxitoxin and several of the conotoxins also bind the same site.
Target Actions Organism ASodium channel protein type 5 subunit alpha blockerHumans USodium channel protein type 1 subunit alpha Not Available Humans USodium channel protein type 2 subunit alpha Not Available Humans USodium channel protein type 3 subunit alpha Not Available Humans USodium channel protein type 8 subunit alpha Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Death has occurred within 17 minutes of ingestion.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Tetrodotoxin is combined with 1,2-Benzodiazepine. Abemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Tetrodotoxin. Abiraterone The risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Tetrodotoxin. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Tetrodotoxin. Acetazolamide The risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Tetrodotoxin. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Tectin / Tetrodin
Categories
- Drug Categories
- Anesthetics
- Anesthetics, Local
- Biological Factors
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Compounds used in a research, industrial, or household setting
- Heterocyclic Compounds, Fused-Ring
- Marine Toxins
- Membrane Transport Modulators
- Noxae
- Peripheral Nervous System Agents
- Poisons
- Quinazolines
- Sensory System Agents
- Sodium Channel Blockers
- Toxic Actions
- Toxins, Biological
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetrodotoxins. These are compounds structurally characterized by the presence of the tetrodotoxin skeleton, which is based on 5,7-(epoxymethanooxy)quinazolin-10-olate moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazanaphthalenes
- Sub Class
- Benzodiazines
- Direct Parent
- Tetrodotoxins
- Alternative Parents
- 1,3-dioxanes / Hydropyrimidines / Monosaccharides / Oxanes / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Guanidines / Orthocarboxylic acid derivatives / Propargyl-type 1,3-dipolar organic compounds show 11 more
- Substituents
- 1,4,5,6-tetrahydropyrimidine / Alcohol / Aliphatic heteropolycyclic compound / Alkanolamine / Alkoxide / Azacycle / Carboximidamide / Cyclic alcohol / Guanidine / Hydrocarbon derivative show 20 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Alkaloids, Tetrodotoxins (C11692)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 3KUM2721U9
- CAS number
- 4368-28-9
- InChI Key
- SLBCPBUVHCASIJ-UFHSVNPDSA-O
- InChI
- InChI=1S/C11H16N3O8/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/h2-7,15-19H,1H2,(H3,12,13,14)/q-1/p+1/t2?,3?,4?,5-,6?,7-,9?,10?,11?/m0/s1
- IUPAC Name
- (11S,13S)-3-amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^{7,11}.0^{1,6}]tetradec-3-en-4-ium-9-olate
- SMILES
- [H][C@]12OC3([O-])OC(C4C(O)[NH+]=C(N)NC4(C1O)[C@@H]3O)C2(O)CO
References
- General References
- Not Available
- External Links
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Cancer / Pain 2 somestatus stop reason just information to hide 2 Recruiting Treatment Chemotherapy Induced Neuropathic Pain / Chemotherapy Induced Peripheral Neuropathy (CIPN) 1 somestatus stop reason just information to hide 2 Terminated Treatment Neuropathic Pain / Pain / Peripheral neuropathy 1 somestatus stop reason just information to hide 1 Completed Basic Science TQT Study 1 somestatus stop reason just information to hide 1 Completed Screening Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source pKa 8.76 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 117.0 mg/mL ALOGPS logP 0.42 ALOGPS logP -4.8 Chemaxon logS -0.5 ALOGPS pKa (Strongest Acidic) 10.4 Chemaxon pKa (Strongest Basic) 9.62 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 8 Chemaxon Polar Surface Area 194.69 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 86.74 m3·mol-1 Chemaxon Polarizability 27.83 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9781 Blood Brain Barrier - 0.6809 Caco-2 permeable - 0.6763 P-glycoprotein substrate Substrate 0.5082 P-glycoprotein inhibitor I Non-inhibitor 0.9376 P-glycoprotein inhibitor II Non-inhibitor 0.988 Renal organic cation transporter Non-inhibitor 0.9066 CYP450 2C9 substrate Non-substrate 0.7925 CYP450 2D6 substrate Non-substrate 0.7989 CYP450 3A4 substrate Non-substrate 0.5602 CYP450 1A2 substrate Non-inhibitor 0.8008 CYP450 2C9 inhibitor Non-inhibitor 0.884 CYP450 2D6 inhibitor Non-inhibitor 0.908 CYP450 2C19 inhibitor Non-inhibitor 0.8374 CYP450 3A4 inhibitor Non-inhibitor 0.9834 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9821 Ames test Non AMES toxic 0.5547 Carcinogenicity Non-carcinogens 0.9196 Biodegradation Not ready biodegradable 0.9587 Rat acute toxicity 2.5238 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9949 hERG inhibition (predictor II) Non-inhibitor 0.8694
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.18642 predictedDeepCCS 1.0 (2019) [M+H]+ 179.54442 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.07344 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Blocker
- General Function
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:1309946, PubMed:21447824, PubMed:23085483, PubMed:23420830, PubMed:25370050, PubMed:26279430, PubMed:26392562, PubMed:26776555). It is a tetrodotoxin-resistant Na(+) channel isoform (PubMed:1309946). This channel is responsible for the initial upstroke of the action potential. Channel inactivation is regulated by intracellular calcium levels (PubMed:19074138). Required for normal electrical conduction including formation of the infranodal ventricular conduction system and normal action potential configuration, as a result of its interaction with XIRP2 (By similarity)
- Specific Function
- Ankyrin binding
- Gene Name
- SCN5A
- Uniprot ID
- Q14524
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:14672992). Plays a key role in brain, probably by regulating the moment when neurotransmitters are released in neurons. Involved in sensory perception of mechanical pain: activation in somatosensory neurons induces pain without neurogenic inflammation and produces hypersensitivity to mechanical, but not thermal stimuli
- Specific Function
- Voltage-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential
- Gene Name
- SCN1A
- Uniprot ID
- P35498
- Uniprot Name
- Sodium channel protein type 1 subunit alpha
- Molecular Weight
- 228969.49 Da
References
- Sage D, Salin P, Alcaraz G, Castets F, Giraud P, Crest M, Mazet B, Clerc N: Na(v)1.7 and Na(v)1.3 are the only tetrodotoxin-sensitive sodium channels expressed by the adult guinea pig enteric nervous system. J Comp Neurol. 2007 Oct 1;504(4):363-78. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:1325650, PubMed:17021166, PubMed:28256214, PubMed:29844171). Implicated in the regulation of hippocampal replay occurring within sharp wave ripples (SPW-R) important for memory (By similarity)
- Specific Function
- Calmodulin binding
- Gene Name
- SCN2A
- Uniprot ID
- Q99250
- Uniprot Name
- Sodium channel protein type 2 subunit alpha
- Molecular Weight
- 227972.64 Da
References
- Sage D, Salin P, Alcaraz G, Castets F, Giraud P, Crest M, Mazet B, Clerc N: Na(v)1.7 and Na(v)1.3 are the only tetrodotoxin-sensitive sodium channels expressed by the adult guinea pig enteric nervous system. J Comp Neurol. 2007 Oct 1;504(4):363-78. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:24157691, PubMed:28235671, PubMed:29466837). May contribute to the regulation of serotonin/5-hydroxytryptamine release by enterochromaffin cells (By similarity). In pancreatic endocrine cells, required for both glucagon and glucose-induced insulin secretion (By similarity)
- Specific Function
- Voltage-gated sodium channel activity
- Gene Name
- SCN3A
- Uniprot ID
- Q9NY46
- Uniprot Name
- Sodium channel protein type 3 subunit alpha
- Molecular Weight
- 226291.905 Da
References
- Sage D, Salin P, Alcaraz G, Castets F, Giraud P, Crest M, Mazet B, Clerc N: Na(v)1.7 and Na(v)1.3 are the only tetrodotoxin-sensitive sodium channels expressed by the adult guinea pig enteric nervous system. J Comp Neurol. 2007 Oct 1;504(4):363-78. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Pore-forming subunit of a voltage-gated sodium channel complex assuming opened or closed conformations in response to the voltage difference across membranes and through which sodium ions selectively pass along their electrochemical gradient (PubMed:24874546, PubMed:25239001, PubMed:25725044, PubMed:26900580, PubMed:29726066, PubMed:33245860, PubMed:36696443, PubMed:36823201). Contributes to neuronal excitability by regulating action potential threshold and propagation (PubMed:24874546, PubMed:25239001, PubMed:25725044, PubMed:26900580, PubMed:29726066, PubMed:33245860, PubMed:36696443, PubMed:36823201)
- Specific Function
- Atp binding
- Gene Name
- SCN8A
- Uniprot ID
- Q9UQD0
- Uniprot Name
- Sodium channel protein type 8 subunit alpha
- Molecular Weight
- 225278.005 Da
References
- Sage D, Salin P, Alcaraz G, Castets F, Giraud P, Crest M, Mazet B, Clerc N: Na(v)1.7 and Na(v)1.3 are the only tetrodotoxin-sensitive sodium channels expressed by the adult guinea pig enteric nervous system. J Comp Neurol. 2007 Oct 1;504(4):363-78. [Article]
Drug created at October 21, 2007 22:24 / Updated at August 26, 2024 19:24