Zetekitoxin AB

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
3D model (JSmol)
ChEMBL
ChemSpider
  • 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
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):
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

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

Mechanism of action

ZTX is an extremely potent sodium channel blocker. It has been shown to block the voltage-gated sodium channels at picomolar concentrations. It is about 580 times more potent than saxitoxin.

Toxicity

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

See also


This page was last updated at 2023-10-28 21:10 UTC. Update now. View original page.

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