TETRODOTOXIN

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 Search

SMILES

[H][C@]12O[C@@]3(O)O[C@]([H])([C@]4([H])[C@@H](O)N=C(N)N[C@]4([C@@H]1O)[C@@H]3O)[C@@]2(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	8 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18243639 | https://www.ncbi.nlm.nih.gov/pubmed/21655148 | https://www.ncbi.nlm.nih.gov/pubmed/22412801

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24607901	Blocker 537

Conditions

Condition	Modality	Highest Phase	Product
Cancer pain 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18243639	Primary	Phase III 656	Unknown Approved Use Unknown
Neuropathic pain 26 Sources: https://clinicaltrials.gov/ct2/show/NCT01655823	Primary	Phase II 1132	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22412801	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 100	binder 5 Sources: https://pubmed.ncbi.nlm.nih.gov/19098433/ \| https://pubmed.ncbi.nlm.nih.gov/23121096/ \| https://pubmed.ncbi.nlm.nih.gov/18529044/

Sourcing

Vendor/Aggregator	ID	URL
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
BOC Sciences	4368-28-9	http://www.bocsci.com/description.asp?cas=4368-28-9
BioSynth	Q-100286	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100286
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
MolPort	MolPort-044-561-240	https://www.molport.com/shop/molecule-link/MolPort-044-561-240
Molnova	M14486	https://www.molnova.com/en/serch-list.html?keywords=M14486
MuseChem	I003550	https://www.musechem.com/product/I003550.html
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

PubMed

Title	Date	PubMed
On the origins and biosynthesis of tetrodotoxin.	2011 Jul	21543051
A multicentre open-label safety and efficacy study of tetrodotoxin for cancer pain.	2011 Jun	21655148
Tetrodotoxin (TTX) as a therapeutic agent for pain.	2012 Feb	22412801
The molecular mystique of tetrodotoxin.	2013 Mar 1	23261990

Patents

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 `Fri Dec 15 15:39:49 UTC 2023` Edited by `admin` on `Fri Dec 15 15:39:49 UTC 2023`
Record UNII	3KUM2721U9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRODOTOXIN

Official 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

tetrodotoxin [INN]

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