Marinobufagenin: Difference between revisions

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{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 379258277
| Watchedfields = changed
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|ImageFile=Marinobufagin.png
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| verifiedrevid = 445026547
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|ImageSize=240
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| ImageFile=Marinobufagin.svg
|IUPACName=
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| ImageSize=240
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|OtherNames=Marinobufagin, Marinobufagenin
| IUPACName=3β,5-Dihydroxy-14,15-epoxy-5β,14β-bufa-20,22-dienolide
| SystematicName=5-[(1''R'',2a''R'',3a''S'',3b''R'',5a''S'',7''S'',9a''R'',9b''S'',11a''R'')-5b,7-Dihydroxy-9a,11a-dimethylhexadecahydronaphtho[1′,2′:6,7]indeno[1,7a-''b'']oxiren-1-yl]-2''H''-pyran-2-one
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| OtherNames=Marinobufagin, Marinobufagenin
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=470-42-8
| CASNo=470-42-8
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| PubChem= 10104
| UNII_Ref = {{fdacite|correct|FDA}}
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| SMILES= C[C@]12CC[C@@H](C[C@]1(CCC3C2CC[C@]4([C@]35[C@H](O5)C[C@@H]4C6=COC(=O)C=C6)C)O)O
| UNII = 3KBT25GV2B
}}
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| PubChem= 11969465
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| SMILES= C[C@]12CC[C@@H](C[C@]1(CCC3C2CC[C@]4([C@]35[C@H](O5)C[C@@H]4C6=COC(=O)C=C6)C)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 10142870
| 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/s1
| InChIKey = JMNQTHQLNRILMH-OBBGIPBRBU
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = JMNQTHQLNRILMH-OBBGIPBRSA-N }}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=24 | H=32 | O=5
| C=24 | H=32 | O=5
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=Toxic
| MainHazards=Toxic
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
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'''Marinobufagin''' is a [[cardiotonic]] [[bufadienolide]] [[steroid]] secreted by the [[toad]] ''[[Bufo rubescens]]''<ref>Cunha Filho GA, Schwartz CA, Resck IS, Murta MM, Lemos SS, Castro MS, Kyaw C, Pires OR Jr, Leite JR, Bloch C Jr, Schwartz EF. Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens. ''Toxicon''. 2005 May;45(6):777-82. PMID 15804527</ref> and other related species such as ''[[Bufo marinus]]''. It is a [[vasoconstrictor]] with effects similar to [[digitalis]].<ref>Fedorova OV, Talan MI, Agalakova NI, Lakatta EG, Bagrov AY. Endogenous ligand of alpha(1) sodium pump, marinobufagenin, is a novel mediator of sodium chloride--dependent hypertension. ''Circulation''. 2002 Mar 5;105(9):1122-7. PMID 11877366</ref>
'''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.<ref>{{cite journal |last1=Tian |first1=Jiang |title=Renal ischemia regulates marinobufagenin release in humans |journal=Hypertension |date=7 September 2010 |volume=56 |issue=5 |pages=914–919 |doi=10.1161/hypertensionaha.110.155564 |pmid=20823380 |pmc=2959137 }}</ref> It is also secreted by the [[toad]] ''[[Bufo rubescens]]''<ref>{{cite journal | pmid = 15804527 | year = 2005 | last1 = Cunha Filho | first1 = GA | last2 = Schwartz | first2 = CA | last3 = Resck | first3 = IS | last4 = Murta | first4 = MM | last5 = Lemos | first5 = SS | last6 = Castro | first6 = MS | last7 = Kyaw | first7 = C | last8 = Pires Jr | first8 = OR | last9 = Leite | first9 = JR | last10 = Bloch | first10 = Carlos | last11 = Schwartz | first11 = Elisabeth Ferroni | title = Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens | volume = 45 | issue = 6 | pages = 777–82 | doi = 10.1016/j.toxicon.2005.01.017 | journal = Toxicon| display-authors = 8 }}</ref> and other related species such as ''[[Bufo marinus]]''. It is a [[vasoconstrictor]] with effects similar to [[digitalis]].<ref>{{cite journal | pmid = 11877366 | year = 2002 | last1 = Fedorova | first1 = OV | last2 = Talan | first2 = MI | last3 = Agalakova | first3 = NI | last4 = Lakatta | first4 = EG | last5 = Bagrov | first5 = AY | title = Endogenous ligand of alpha(1) sodium pump, marinobufagenin, is a novel mediator of sodium chloride--dependent hypertension | volume = 105 | issue = 9 | pages = 1122–7 | journal = Circulation | doi=10.1161/hc0902.104710| doi-access = free }}</ref>


==References==
==References==
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{{Cardiac glycosides}}
{{Cardiac glycosides}}


[[Category:Vertebrate toxins]]
[[Category:Amphibian toxins]]
[[Category:Epoxides]]
[[Category:Epoxides]]
[[Category:Bufanolides]]
[[Category:Bufanolides]]
[[Category:Alcohols]]
[[Category:Diols]]
[[Category:Heterocyclic compounds with 5 rings]]



{{med-toxic-stub}}
{{med-toxic-stub}}
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