Jump to content
 







Main menu
    


Navigation  


●Main page
 ●Contents
 ●Current events
 ●Random article
 ●About Wikipedia
 ●Contact us
 ●Donate
  



Contribute  


●Help
 ●Learn to edit
 ●Community portal
 ●Recent changes
 ●Upload file
  







Search  

































●Create account

●Log in
 









●Create account
 ● Log in
  



Pages for logged out editors learn more  


●Contributions
 ●Talk
  


















Contents

   



(Top)
  


1 Structure  




2 Mechanism of action  




3 Toxicity  




4 See also  




5 References  













Zetekitoxin AB







Add links
  








●Article
 ●Talk
  
















●Read
 ●Edit
 ●View history
  







Tools
    


Actions  


●Read
 ●Edit
 ●View history
  



General  


●What links here
 ●Related changes
 ●Upload file
 ●Special pages
 ●Permanent link
 ●Page information
 ●Cite this page
 ●Get shortened URL
 ●Download QR code
 ●Wikidata item
  



Print/export  


●Download as PDF
 ●Printable version
  















Appearance
    

 





From Wikipedia, the free encyclopedia
  

Zetekitoxin AB
Names
IUPAC name

[(3R,5S,6S,11R,12S,14Z,16S,17Z)-14,17-Diamino-19,19-dihydroxy-6-(hydroxymethyl)-10-oxo-3-(sulfooxy)-8-oxa-1,9,13,15,18-pentaazapentacyclo[9.5.2.1~3,16~.0~5,9~.0~12,16~]nonadeca-14,17-dien-13-yl]methyl hydroxycarbamate

Other names

ZTX

Identifiers

CAS Number

3D model (JSmol)
ChEMBL
ChemSpider

PubChem CID

  • InChI=1S/C16H24N8O12S/c17-11-19-8-9-15(20-12(18)22(9)5-34-13(27)21-30)16(28,29)14(4-23(11)15,36-37(31,32)33)1-7-6(2-25)3-35-24(7)10(8)26/h6-9,25,28-30H,1-5H2,(H2,17,19)(H2,18,20)(H,21,27)(H,31,32,33)/t6-,7-,8+,9-,14+,15-/m0/s1

    Key: BJJIKPMJNDTIHW-FGWFJEOOSA-N

  • [H]/N=C/1\N2[C@@]34N/C(=N/[H])/N([C@H]3[C@@H](N1)C(=O)N5OC[C@@H]([C@@H]5C[C@@](C2)([C@]4(O)O)OS(=O)(=O)O)CO)COC(=O)NO

Properties

Chemical formula

 C16H24N8O12S
Molar mass 552.47 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

 Extremely toxic
Lethal dose or concentration (LD, LC):

LD50 (median dose)

 11 μg/kg (mice)
Related compounds

Related compounds

 Saxitoxin
Neosaxitoxin
Tetrodotoxin

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Zetekitoxin AB (ZTX) is a guanidine alkaloid found in the Panamanian golden frog Atelopus zeteki. It is an extremely potent neurotoxin.

Structure[edit]

ZTX is a guanidine alkaloid. It's structurally related to saxitoxin, but with some differences. ZTX contains an isoxazolidine ring, a sulfonate group and an N-hydroxycarbamate group.[2]

Mechanism of action[edit]

ZTX is an extremely potent sodium channel blocker. It has been shown to block the voltage-gated sodium channelsatpicomolar concentrations. It is about 580 times more potent than saxitoxin.[2]

Toxicity[edit]

ZTX is an extremely potent neurotoxin. The LD50 of ZTX in mice is 11 μg/kg.[3]

See also[edit]

References[edit]

  1. ^ Chambers, Michael. "ChemIDplus - 0062996387 - Zetekitoxin AB - Searchable synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
  • ^ a b Yotsu-Yamashita, M.; Kim, Y. H.; Dudley, S. C.; Choudhary, G.; Pfahnl, A.; Oshima, Y.; Daly, J. W. (22 March 2004). "The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: A potent sodium-channel blocker". Proceedings of the National Academy of Sciences. 101 (13): 4346–4351. Bibcode:2004PNAS..101.4346Y. doi:10.1073/pnas.0400368101. PMC 384749. PMID 15070720.
  • ^ Brown, George B.; Kim, Yong H.; Küntzel, Heiner; Mosher, Harry S.; Fuhrman, Geraldine J.; Fuhrman, Frederick A. (January 1977). "Chemistry and pharmacology of skin toxins from the frog Atelopus Zeteki (Atelopidtoxin: Zetekitoxin)". Toxicon. 15 (2): 115–128. doi:10.1016/0041-0101(77)90030-7. PMID 558664.
    • Stub icon

    This neurotoxin article is a stub. You can help Wikipedia by expanding it.

  • t
  • e

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Zetekitoxin_AB&oldid=1224332411"
    Categories: 
    ●Neurotoxins
     ●Voltage-gated sodium channel blockers
     ●Guanidine alkaloids
     ●Alcohols
     ●Geminal diols
     ●Isoxazolidines
     ●Carbamates
     ●Lactams
     ●Hydroxamic acids
     ●Nitrogen heterocycles
     ●Poison dart frogs
     ●Sulfate esters
     ●Amphibian toxins
     ●Heterocyclic compounds with 5 rings
     ●Neurotoxin stubs
     Hidden categories: 
    ●Articles without InChI source
     ●Articles without KEGG source
     ●Articles without UNII source
     ●Articles with changed CASNo identifier
     ●Articles containing unverified chemical infoboxes
     ●Articles with short description
     ●Short description matches Wikidata
     ●All stub articles
      


    ●This page was last edited on 17 May 2024, at 18:57 (UTC).
    ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.


    ●Privacy policy
    ●About Wikipedia
    ●Disclaimers
    ●Contact Wikipedia
    ●Code of Conduct
    ●Developers
    ●Statistics
    ●Cookie statement
    ●Mobile view


    Wikimedia Foundation
    Powered by MediaWiki