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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H17N3O8
Molecular Weight 319.268
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRODOTOXIN

SMILES

NC1=N[C@H](O)[C@H]2[C@H]3O[C@]4(O)O[C@@H]([C@@H](O)[C@@]2(N1)[C@@H]4O)[C@]3(O)CO

InChI

InChIKey=CFMYXEVWODSLAX-QOZOJKKESA-N
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

HIDE SMILES / InChI
Molecular Formula C11H17N3O8
Molecular Weight 319.268
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Tetrodotoxin (TTX) is a potent marine neurotoxin that blocks voltage-gated sodium channels (VGSCs). VGSCs play a critical role in neuronal function under both physiological and pathological conditions. TTX has been extensively used to functionally characterize VGSCs, which can be classified as TTX-sensitive or TTX-resistant channels according to their sensitivity to this toxin. Wex Pharmaceuticals is investigating tetrodotoxin for the treatment of chronic and breakthrough pain. The toxin is currently undergoing Phase III clinical trials in Canada as a systemic analgesic for inadequately controlled pain due to advanced cancer, especially where the pain has neuropathic features. In addition, TTX is in Phase II clinical trials to study its ability in moderate to severe neuropathic pain caused by chemotherapy.

CNS Activity

CNS Non-penetrant
1040
Curator's Comment: cross the blood brain barrier very poorly

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
555
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.9914 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/32784930
45 μL single, subcutaneous
dose: 45 μL
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
TETRODOTOXIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6.4983 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/32784930
45 μL single, subcutaneous
dose: 45 μL
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
TETRODOTOXIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.28 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/32784930
45 μL single, subcutaneous
dose: 45 μL
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
TETRODOTOXIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Nav1.5
119
Sourcing

Sourcing

Vendor/AggregatorIDURL
AbovChem LLC
HY-12526
http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-12526A
AbovChem LLC
HY-12526A
http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-12526A
AstaTech
43647
http://astatechinc.com/CPSResult.php?CRNO=43647
BioSynth
Q-100286
https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100286
BOC Sciences
4368-28-9
http://www.bocsci.com/description.asp?cas=4368-28-9
Cayman Chemical
14963
http://www.caymanchem.com/app/template/Product.vm/catalog/14963
Cayman Chemical
14964
http://www.caymanchem.com/app/template/Product.vm/catalog/14964
eMolecules
168694274
https://orderbb.emolecules.com/search/#?query=168694274
eMolecules
174478956
https://orderbb.emolecules.com/search/#?query=174478956
eMolecules
194913683
https://orderbb.emolecules.com/search/#?query=194913683
eMolecules
303479450
https://orderbb.emolecules.com/search/#?query=303479450
eMolecules
48601009
https://orderbb.emolecules.com/search/#?query=48601009
Molnova
M14486
https://www.molnova.com/en/serch-list.html?keywords=M14486
MolPort
MolPort-044-561-240
https://www.molport.com/shop/molecule-link/MolPort-044-561-240
MuseChem
I003550
https://www.musechem.com/product/I003550.html
PubMed

PubMed

TitleDatePubMed
The molecular mystique of tetrodotoxin.
2013-03-01
Tetrodotoxin (TTX) as a therapeutic agent for pain.
2012-02
Tetrodotoxin alleviates acute heroin withdrawal syndrome: a multicentre, randomized, double-blind, placebo-controlled study.
2011-08
On the origins and biosynthesis of tetrodotoxin.
2011-07
A multicentre open-label safety and efficacy study of tetrodotoxin for cancer pain.
2011-06
Tetrodotoxin for moderate to severe cancer pain: a randomized, double blind, parallel design multicenter study.
2008-04
Patents

Patents

US1058643
1
US6562968
1

Sample Use Guides

In Vivo Use Guide
subcutaneous 30 µg twice daily for 4 days intramuscular injection (1 ml volume), twice a day for four consecutive days.
Route of Administration: Other
In Vitro Use Guide
There was used micro-electrode array (MEA) recordings as an integrated measure of neurotransmission to demonstrate that tetrodotoxin inhibited neuronal electrical activity in both primary rat cortical cultures and human-induced pluripotent stem cell (hIPSC)-derived iCell® neurons in co-culture with hIPSC-derived iCell® astrocytes, with IC50 values of 7 and 10nM, respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:04:38 GMT 2025
Edited
by admin
on Mon Mar 31 18:04:38 GMT 2025
Record UNII
3KUM2721U9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRODOTOXIN
INN   MI   WHO-DD  
INN  
Official Name English
tetrodotoxin [INN]
Preferred Name English
TARICHATOXIN
Common Name English
TECTIN
Common Name English
ARAREGAI TOXIN
Common Name English
5,9:7,10A-DIMETHANO-10AH-(1,3)DIOXOCINO(6,5-D)PYRIMIDINE-4,7,10,11,12-PENTOL, 2-AMINO-1,4,4A,5,9,10-HEXAHYDRO-12-(HYDROXYMETHYL)-, (4R,4AR,5R,7S,9S,10S,10AR,11S,12S)-
Systematic Name English
TETRODOTOXINE
Common Name English
TETRODOTOXIN [MI]
Common Name English
Tetrodotoxin [WHO-DD]
Common Name English
SPHEROIDINE
Common Name English
BABYLONIA JAPONICA TOXIN 1
Common Name English
PFT-1 TOXIN
Common Name English
TTX
Code English
BJT 1
Common Name English
MACULOTOXIN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C93038
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
NCI_THESAURUS C688
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
Code System Code Type Description
PUBCHEM
11174599
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
CAS
4368-28-9
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
FDA UNII
3KUM2721U9
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
DRUG BANK
DB05232
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
SMS_ID
300000037002
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
WIKIPEDIA
TETRODOTOXIN
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
INN
10243
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
MESH
D013779
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
CHEBI
9506
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
NCI_THESAURUS
C78845
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
HSDB
3543
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
MERCK INDEX
m10664
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
224-458-8
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID10881342
Created by admin on Mon Mar 31 18:04:38 GMT 2025 , Edited by admin on Mon Mar 31 18:04:38 GMT 2025
PRIMARY
Related Record Type Details
SODIUM CHANNEL PROTEIN TYPE 2 SUBUNIT ALPHA
TARGET -> INHIBITOR
IC50
SODIUM CHANNEL PROTEIN TYPE 4 SUBUNIT ALPHA
TARGET -> INHIBITOR
SODIUM CHANNEL PROTEIN TYPE 3 SUBUNIT ALPHA
TARGET -> INHIBITOR
IC50
SODIUM CHANNEL PROTEIN TYPE 1 SUBUNIT ALPHA
TARGET -> INHIBITOR
IC50
Related Record Type Details
Structure of TETRODOTOXIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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