Arenobufagin

Arenobufagin

IUPAC name 5-[(3S,5R,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxo-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
Other names Arenobufagin
Identifiers
CAS number	464-74-4
PubChem	10051
ChemSpider	20051196^Y
Jmol-3D images	Image 1
SMILES C[C@]12CC[C@@H](C[C@H]1CCC3C2[C@@H](C(=O)[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O)O
InChI InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19-20,25,27,29H,4-5,7-11H2,1-2H3/t14-,15+,16-,17-,19-,20+,22+,23+,24+/m1/s1 ^Y Key: JGDCRWYOMWSTFC-AZGSIFHYSA-N ^Y
Properties
Molecular formula	C₂₄H₃₂O₆
Molar mass	416.51 g mol⁻¹
Hazards
Main hazards	Toxic
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Arenobufagin is a cardiotoxic bufanolide steroid secreted by the Argentine toad Bufo arenarum.^[1] It has effects similar to digitalis, blocking the Na+/K+ pump in heart tissue.^[2]

References

Toxins (enterotoxin · neurotoxin · hemotoxin · cardiotoxin · phototoxin)

Bacterial
toxins

Exotoxin

Gram
positive

Bacilli	Clostridium: tetani (Tetanospasmin) · perfringens (Alpha toxin, Enterotoxin) · difficile (A, B) · botulinum (Botox) other: Anthrax toxin · Listeriolysin O

Cocci	Streptolysin · Leukocidin (Panton-Valentine leukocidin) · Staphylococcus (Staphylococcus aureus alpha/beta/delta, Exfoliatin, Toxic shock syndrome toxin, SEB)

Actinobacteria	Cord factor · Diphtheria toxin

Gram
negative

Shiga toxin · Verotoxin/shiga-like toxin (E. coli) · E. coli heat-stable enterotoxin/enterotoxin · Cholera toxin · Pertussis toxin · Pseudomonas exotoxin · Extracellular adenylate cyclase

Mechanisms

type I (Superantigen) · type II (Pore-forming toxin) · type III (AB toxin/AB5)

Endotoxin

Lipopolysaccharide (Lipid A) · Bacillus thuringiensis delta endotoxin

Virulence
factor

Clumping factor A · Fibronectin binding protein A

Mycotoxins

Aflatoxin · Amatoxin (alpha-amanitin, beta-amanitin, · Beta-nitropropionic acid · gamma-amanitin, epsilon-amanitin) · Citrinin · Cytochalasin · Ergotamine · Fumonisin (Fumonisin B1, Fumonisin B2) · Gliotoxin · Ibotenic acid · Muscimol · Ochratoxin · Patulin · Phalloidin · Sterigmatocystin · Trichothecene · Vomitoxin · Zeranol · Zearalenone

Invertebrates

scorpion: Androctonus australis hector insect toxin, Charybdotoxin, Maurotoxin, Agitoxin, Margatoxin, Slotoxin, Scyllatoxin, Hefutoxin, Lq2, Birtoxin, Bestoxin, BmKAEP, Phaiodotoxin, Imperatoxin ·
spider: Latrotoxin (Alpha-latrotoxin) · CSTX · Cupiennins · PhTx3 · Stromatoxin · Vanillotoxin · Huwentoxin
mollusca: Conotoxin · Eledoisin · Onchidal · Saxitoxin · Tetrodotoxin

Vertebrates

fish: Ciguatera · Tetrodotoxin

amphibian: (+)-Allopumiliotoxin 267A · Batrachotoxin · Bufotoxins (Arenobufagin, Bufotalin, Bufotenin · Cinobufagin, Marinobufagin) · Epibatidine · Histrionicotoxin · Pumiliotoxin 251D · Samandarin · Samandaridine · Tarichatoxin

reptile/snake venom: Bungarotoxin (Alpha-Bungarotoxin, Beta-Bungarotoxin) · Calciseptine · Taicatoxin · Calcicludine · Cardiotoxin III

note: some toxins are produced by lower species and pass through intermediate species

M: TOX

gen / txn

pto

ant

Cardiac glycosides (C01A)

Bufadienolides

Bufo	Arenobufagin Bufotalin Cinobufagin Marinobufagin

Scilla	Proscillaridin Scilliroside

Cardenolides

Digitalis	Acetyldigitoxin Acetyldigoxin Digitoxin^# Digoxin^# Lanatoside C Deslanoside Metildigoxin Gitoformate

Kalanchoe	Daigremontianin

Strophanthus	Ouabain (g-Strophanthin) k-Strophanthin Cymarin

Thevetia	Peruvoside

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: HRT

anat/phys/devp

noco/cong/tumr, sysi/epon, injr

proc, drug (C1A/1B/1C/1D), blte

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