Marinobufagenin - Misplaced Pages

Marinobufagenin
Names

IUPAC name 3β,5-Dihydroxy-14,15-epoxy-5β,14β-bufa-20,22-dienolide
Systematic IUPAC name 5-indenooxiren-1-yl]-2H-pyran-2-one
Other names Marinobufagin, Marinobufagenin
Identifiers
CAS Number	470-42-8
3D model (JSmol)	Interactive image
ChemSpider	10142870
PubChem CID	11969465
UNII	3KBT25GV2B
CompTox Dashboard (EPA)	DTXSID5041063
InChI InChI=1S/C24H32O5/c1-21-8-5-15(25)12-23(21,27)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)29-19)14-3-4-20(26)28-13-14/h3-4,13,15-19,25,27H,5-12H2,1-2H3/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1Key: JMNQTHQLNRILMH-OBBGIPBRSA-N InChI=1/C24H32O5/c1-21-8-5-15(25)12-23(21,27)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)29-19)14-3-4-20(26)28-13-14/h3-4,13,15-19,25,27H,5-12H2,1-2H3/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1Key: JMNQTHQLNRILMH-OBBGIPBRBU
SMILES C12CC(C1(CCC3C2CC4(35(O5)C4C6=COC(=O)C=C6)C)O)O
Properties
Chemical formula	C₂₄H₃₂O₅
Molar mass	400.515 g·mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Marinobufagenin (marinobufagin) is a cardiotonic bufadienolide steroid. It can be found in the plasma and urine of human subjects with myocardial infarction, kidney failure, and heart failure. It is also secreted by the toad Bufo rubescens and other related species such as Bufo marinus. It is a vasoconstrictor with effects similar to digitalis.

References

Tian, Jiang (7 September 2010). "Renal ischemia regulates marinobufagenin release in humans". Hypertension. 56 (5): 914–919. doi:10.1161/hypertensionaha.110.155564. PMC 2959137. PMID 20823380.
Cunha Filho, GA; Schwartz, CA; Resck, IS; Murta, MM; Lemos, SS; Castro, MS; Kyaw, C; Pires Jr, OR; et al. (2005). "Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens". Toxicon. 45 (6): 777–82. doi:10.1016/j.toxicon.2005.01.017. PMID 15804527.
Fedorova, OV; Talan, MI; Agalakova, NI; Lakatta, EG; Bagrov, AY (2002). "Endogenous ligand of alpha(1) sodium pump, marinobufagenin, is a novel mediator of sodium chloride--dependent hypertension". Circulation. 105 (9): 1122–7. doi:10.1161/hc0902.104710. PMID 11877366.

Toxins

Clostridium:	tetani Tetanospasmin Tetanolysin 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 Staphylococcal Enterotoxin B (SEB)

Lipopolysaccharide
- Lipid A
Bacillus thuringiensis delta endotoxin
- Cry1Ac
- Cry3Bb1
Other B. thuringiensis toxins
- Cry6Aa
- Cry34Ab1

Virulence
factor

Mycotoxins

Aflatoxin
Amatoxin (alpha-amanitin, beta-amanitin, gamma-amanitin, epsilon-amanitin)
beta-Nitropropionic acid
Citrinin
Cytochalasin
Ergotamine
Fumonisin (Fumonisin B1, Fumonisin B2, Fumonisin B3, Fumonisin B4)
Gliotoxin
Ibotenic acid
Lolitrem B
Muscimol
Orellanine
Ochratoxin
Patulin
Phalloidin
Sterigmatocystin
Trichothecene
Vomitoxin
Zeranol
Zearalenone

Plant toxins

Invertebrate
toxins

Scorpion:	Androctonus australis hector insect toxin Charybdotoxin Maurotoxin Agitoxin Margatoxin Slotoxin Scyllatoxin Hefutoxin HgeTx1 HsTx1 Kaliotoxin Lq2 Birtoxin Bestoxin BmKAEP Phaiodotoxin Imperatoxin Pi3
Spider:	Latrotoxin Alpha-latrotoxin CSTX Cupiennins PhTx3 Stromatoxin Vanillotoxin Huwentoxin
Mollusca:	Conotoxin Eledoisin Onchidal Saxitoxin Tetrodotoxin

Vertebrate
toxins

Fish:	Ciguatoxin Tetrodotoxin
Amphibian:	(+)-Allopumiliotoxin 267A Batrachotoxin Bufotoxins Arenobufagin Bufotalin Bufotenin Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB
Reptile/ Snake venom:	Bungarotoxin α-Bungarotoxin β-Bungarotoxin Calciseptine Taicatoxin Calcicludine Cardiotoxin III

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

Category

Cardiac glycosides (C01A)

Bufadienolides

Bufo	Arenobufagin Bufotalin Cinobufagin Marinobufagin
Scilla	Proscillaridin Scilliroside
Kalanchoe	Daigremontianin

Cardenolides

Digitalis	Acetyldigitoxin Acetyldigoxin Digitoxin Digoxin Lanatoside C Deslanoside Metildigoxin Gitoformate
Strophanthus	Ouabain (g-Strophanthin) k-Strophanthin Cymarin
Thevetia	Peruvoside

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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