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Revision as of 13:38, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 447547117 of page Sanguinarine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').		Latest revision as of 04:13, 25 March 2024 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,465 edits auto mw
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			{{Short description|Chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
	{{Drugbox		{{Drugbox
			| Verifiedfields = changed
	| verifiedrevid = 444095870		| verifiedrevid = 464386933
	| IUPAC_name = 13-Methyl-benzodioxolo-1,3-dioxolophenanthridinium		| IUPAC_name = 13-Methyl-benzodioxolo-1,3-dioxolophenanthridinium
			| image = ]
	| image = sanguinarine structure.png
			| image2 = ]
	<!--Clinical data-->		<!--Clinical data-->
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	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->		| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	| legal_status =		| legal_status =
	| routes_of_administration =		| routes_of_administration =
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
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	| metabolism =		| metabolism =
	| elimination_half-life =		| elimination_half-life =
	| excretion =		| excretion =
	<!--Identifiers-->		<!--Identifiers-->
			| CAS_number_Ref = {{cascite|changed|??}}
	| CAS_number = <!-- blanked - oldvalue: 2447-54-3 -->		| CAS_number = 2447-54-3
	| ATC_prefix = none		| ATC_prefix = none
	| ATC_suffix =		| ATC_suffix =
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 417799		| ChEMBL = 417799
	| PubChem = 5154		| PubChem = 5154
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	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 17183		| ChEBI = 17183
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C06162
	<!--Chemical data-->		<!--Chemical data-->
	| C=20 | H=14 | N=1 | O=4		| C=20 | H=14 | N=1 | O=4
	| molecular_weight = 332.09
	| smiles = O1c3c(OC1)c2c(c5c(c2cc3)ccc6cc4OCOc4cc56)C		| smiles = O1c3c(OC1)c2c(c5c(c2cc3)ccc6cc4OCOc4cc56)C
	| InChI = 1/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
	| InChIKey = INVGWHRKADIJHF-UHFFFAOYAZ
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1		| StdInChI = 1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
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	| StdInChIKey = INVGWHRKADIJHF-UHFFFAOYSA-N		| StdInChIKey = INVGWHRKADIJHF-UHFFFAOYSA-N
	}}		}}
			'''Sanguinarine''' is a polycyclic quaternary ]. It is extracted from some plants, including the ] plant, from whose scientific name, ''Sanguinaria canadensis,'' its name is derived; the Mexican prickly poppy ('']'');<ref name="Santos_Adkilen_1932">{{ cite journal | vauthors = Santos AC, Adkilen P | title = The Alkaloids of ''Argemone Mexicana'' | journal = Journal of the American Chemical Society | year = 1932 | volume = 54 | issue = 7 | pages = 2923–2924 | doi = 10.1021/ja01346a037 }}</ref> ''];'' and ''].''
			==Toxicity==
			Sanguinarine is a toxin that kills animal cells through its action on the ] transmembrane protein.<ref>{{ cite journal | vauthors = Pitts BJ, Meyerson LR | title = Inhibition of Na,K-ATPase Activity and Ouabain Binding by Sanguinarine | journal = Drug Development Research | year = 1981 | volume = 1 | issue = 1 | pages = 43–49 | doi = 10.1002/ddr.430010105 | s2cid = 84619967 }}</ref> ] is a disease that results from ingesting sanguinarine.<ref>{{cite journal | vauthors = Das M, Khanna SK | title = Clinicoepidemiological, toxicological, and safety evaluation studies on argemone oil | journal = Critical Reviews in Toxicology | volume = 27 | issue = 3 | pages = 273–297 | date = May 1997 | pmid = 9189656 | doi = 10.3109/10408449709089896 }}</ref>
			If applied to the skin, sanguinarine may cause a massive scab of dead flesh where it killed the cells where it was applied, called an '']''. For this reason, sanguinarine is termed an ].<ref>{{cite journal | vauthors = Cienki JJ, Zaret L | title = An Internet misadventure: bloodroot salve toxicity | journal = Journal of Alternative and Complementary Medicine | volume = 16 | issue = 10 | pages = 1125–1127 | date = October 2010 | pmid = 20932193 | doi = 10.1089/acm.2010.0140 }}</ref>
			It is said to be 2.5 times more toxic than ].
			== Alternative medicine ==
			Native Americans once used sanguinarine in the form of bloodroot as a medical remedy, believing it had curative properties as an ], respiratory aid, and for a variety of ailments.<ref>{{Cite web|url=http://naeb.brit.org/uses/36993/ |title= Papaveraceae Sanguinaria canadensis L. | work = BRIT - Native American Ethnobotany Database| via = herb.umd.umich.edu|language=en|access-date=2017-05-07}}</ref> In Colonial America, sanguinarine from bloodroot was used as a wart remedy. Later, in 1869, William Cook's ''The Physiomedical Dispensatory'' included information on the preparation and uses of sanguinarine.<ref>{{Cite web|url=http://www.henriettesherbal.com/eclectic/cook/SANGUINARIA_CANADENSIS.htm|title=Sanguinaria Canadensis. Blood root, Red puccoon, Red turmeric. | work = Henriette's Herbal Homepage |access-date=2017-05-07}}</ref> During the 1920s and 1930s, sanguinarine was the chief component of "Pinkard's Sanguinaria Compound," a drug sold by ]. Pinkard advertised the compound as "a treatment, remedy, and cure for pneumonia, coughs, weak lungs, asthma, kidney, liver, bladder, or any stomach troubles, and effective as a great blood and nerve tonic." In 1931, several samples of the compound were seized by federal officials who determined Pinkard's claims to be fraudulent. Pinkard pleaded guilty in court and accepted a fine of $25.00.<ref>{{Cite web|url=https://ceb.nlm.nih.gov/fdanj/handle/123456789/55165|title=FDA Notices of Judgment Collection, 1908-1966|website=ceb.nlm.nih.gov|access-date=2017-05-07}}</ref>
			More recently, sanguinarine from bloodroot has been promoted by many ] companies as a treatment or cure for cancer; however, the ] warns that products containing bloodroot, or other sanguinarine-based plants, have no proven anti-cancer effects, and that they should be avoided on those grounds.<ref>{{cite web |title=Do Not Use: Black Salve is Dangerous and Called by Many Names |url=https://www.fda.gov/consumers/consumer-updates/do-not-use-black-salve-dangerous-and-called-many-names |website=FDA |access-date=2020-10-13}}</ref> Meanwhile, Australian ] also advise consumers not to purchase or use products marketed as containing Sanguinaria canadensis to cure or treat cancer, including certain types of skin cancer.<ref>{{cite web |title=Black and red salves in treating cancer |url=https://www.tga.gov.au/alert/black-and-red-salves-treating-cancer |website=TGA |access-date=19 March 2012}}</ref> Indeed, oral use of such products has been associated with ], a possible precursor of ].<ref>{{Cite book|title=Oral & maxillofacial pathology | vauthors = Neville BW |date=2002-01-01|publisher=W.B. Saunders|isbn=0721690033|oclc=899021983}}</ref> In addition, the escharotic form of sanguinarine, applied to the skin for skin cancers, may leave cancerous cells alive in the skin while creating a significant scar. For this reason it is not recommended as a skin cancer treatment.<ref>{{cite journal | vauthors = Sivyer GW, Rosendahl C | title = Application of black salve to a thin melanoma that subsequently progressed to metastatic melanoma: a case study | journal = Dermatology Practical & Conceptual | volume = 4 | issue = 3 | pages = 77–80 | date = July 2014 | pmid = 25126466 | pmc = 4132006 | doi = 10.5826/dpc.0403a16 }}</ref><ref>{{Cite web|url=https://www.aad.org/media/news-releases/beware-of-black-salve|title=Beware of black salve | work = American Academy of Dermatology |access-date=2018-07-02}}</ref>
			==Biosynthesis==
			In plants, sanguinarine biosynthesis begins with 4-hydroxyphenyl-acetaldehyde and ]. These two compounds are combined to form norcoclaurine. Next, methyl groups are added to form ''N''-methylcoclaurine. The enzyme ] subsequently adds a hydroxyl group, forming 3'-hydroxy-''N''-methylcoclaurine. The addition of another methyl group transforms this compound into ].
			Notably, biosynthesis of sanguinarine up to this point is virtually identical to that of ]. However, instead of being converted to ] (as in the biosynthesis of morphine), reticuline is converted to scoulerine via berberine bridge enzyme (BBE). As such, this is the commitment step in the sanguinarine pathway.<ref name="Alcantara_2005">{{cite journal | vauthors = Alcantara J, Bird DA, Franceschi VR, Facchini PJ | title = Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment | journal = Plant Physiology | volume = 138 | issue = 1 | pages = 173–183 | date = May 2005 | pmid = 15849302 | pmc = 1104173 | doi = 10.1104/pp.105.059287 }}</ref> Although it is unknown exactly how scoulerine proceeds down the biosynthetic pathway, it is eventually converted to ]. The precursor to sanguinarine, dihydrosanguinarine is converted to the final toxin via the action of ].<ref>{{cite book | chapter-url = http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/alkaloid/macarpine.html | chapter = Chelirubine, Macarpine, and Sanguinarine Biosynthesis | publisher = International Union of Biochemistry and Molecular Biology | title = Recommendations on Biochemical & Organic Nomenclature, Symbols & Terminology etc. | url = http://www.chem.qmul.ac.uk/iubmb/ }}</ref>
			]
			== See also ==
			* ], a plant-derived compound having a chemical classification similar to that of sanguinarine.
			* ]
			== References ==
			{{reflist}}
			]
			]
			]
			]
			]