| Revision as of 15:58, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{drugbox}} taken from revid 459658524 of page Vinpocetine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 05:29, 12 May 2024 edit Boghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,925 edits consistent citation formatting |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 458290877 |
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| verifiedrevid = 470630524 |
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| IUPAC_name = <small>(3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester</small> |
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| IUPAC_name = (3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester |
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| image = Vinpocetine.svg |
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| image = Vinpocetine.svg |
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| width = 200px |
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| width = 200px |
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| image2 = Vinpocetine ball-and-stick.png |
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| width2 = 200px |
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<!--Clinical data--> |
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<!--Clinical data-->| tradename = |
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| Drugs.com = {{drugs.com|international|vinpocetine}} |
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| tradename = |
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| pregnancy_category = Not recommended<ref name=FDA2019Preg/> |
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| Drugs.com = {{drugs.com|international|vinpocetine}} |
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| legal_EU = Rx-only |
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| pregnancy_category = not recommended |
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| legal_EU_comment = {{citation needed|date=December 2016}} |
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| legal_status = OTC |
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| legal_US = Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in ]s, ], or ] is unlawful; otherwise uncontrolled. <ref>{{Cite web |date=February 22, 2023 |title=Vinpocetine in Dietary Supplements |url=https://www.fda.gov/food/dietary-supplement-ingredient-directory/vinpocetine-dietary-supplements |access-date=June 9, 2023 |website=]}}</ref> |
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| routes_of_administration = oral, intravenous |
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| routes_of_administration = Oral, intravenous |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data-->| bioavailability = 56.6 ± 8.9% |
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| metabolism = hepatic |
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| bioavailability = 56.6 +/- 8.9% |
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| elimination_half-life = 2.54 ± 0.48 hours |
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| metabolism = hepatic |
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| excretion = renal |
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| elimination_half-life = 2.54 +/- 0.48 hours |
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| excretion = renal |
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<!--Identifiers--> |
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<!--Identifiers-->| IUPHAR_ligand = 5285 |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 42971-09-5 --> |
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| CAS_number = 42971-09-5 |
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| ATC_prefix = N06 |
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| ATC_prefix = N06 |
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| ATC_suffix = BX18 |
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| ATC_suffix = BX18 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 71752 |
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| ChEMBL = 71752 |
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| PubChem = 443955 |
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| PubChem = 443955 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 392007 |
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| ChemSpiderID = 392007 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 543512OBTC |
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| UNII = 543512OBTC |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D01371 |
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| KEGG = D01371 |
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<!--Chemical data--> |
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<!--Chemical data-->| C = 22 |
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| C=22 | H=26 | N=2 | O=2 |
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| H = 26 |
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| N = 2 |
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| molecular_weight = 350.454 g/mol |
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| O = 2 |
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| smiles = O=C(OCC)C=4n1c3c(c2ccccc12)CCN53(C=4)(CCC5)CC |
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| smiles = O=C(OCC)C=4n1c3c(c2ccccc12)CCN53(C=4)(CCC5)CC |
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| InChI = 1/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = DDNCQMVWWZOMLN-IRLDBZIGBY |
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| StdInChI = 1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1 |
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| StdInChIKey = DDNCQMVWWZOMLN-IRLDBZIGSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DDNCQMVWWZOMLN-IRLDBZIGSA-N |
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}} |
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}} |
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'''Vinpocetine''' ('''ethyl apovincaminate''') is a synthetic ] of the ] ], differing by the removal of a ] group and by being the ethyl rather than the methyl ester of the underlying carboxylic acid. Vincamine is extracted from either the seeds of '']'' or the leaves of '']'' (lesser periwinkle). |
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==Medical uses== |
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Vinpocetine has been used in many Asian and European countries for treatment of cerebrovascular disorders such as stroke and dementia for over three decades.<ref name="pmid29183836">{{cite journal | vauthors = Zhang YS, Li JD, Yan C | title = An update on vinpocetine: New discoveries and clinical implications | journal = European Journal of Pharmacology | volume = 819 | issue = | pages = 30–34 | date = January 2018 | pmid = 29183836 | doi = 10.1016/j.ejphar.2017.11.041 | doi-access = free | pmc = 5766389 }}</ref> |
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The ] has tentatively ruled that vinpocetine, due to its synthetic nature and proposed therapeutic uses, is ineligible to be marketed as ] under the ].<ref name="Newsweek_011217">{{cite magazine| vauthors = Schmitt R |title=Marketers exploit the aged with unproven brain-health claims|url=http://www.newsweek.com/marketers-exploit-aged-unproven-brain-health-claims-541709?rx=us|access-date=January 18, 2016|magazine=]|date=January 12, 2017}}</ref><ref name="NI_090816">{{cite web| vauthors = Hank S |title=FDA rules vinpocetine not a legal dietary ingredient despite successful NDI filings |url=http://www.nutraingredients-usa.com/Regulation/FDA-rules-vinpocetine-not-a-legal-dietary-ingredient-despite-successful-NDI-filings|website=NutraIngredients|date=7 September 2016 |publisher=William Reed Business Media, England|access-date=September 8, 2016}}</ref><ref name="NW_011816">{{cite web|title=FDA Concludes Vinpocetine Ineligible as a Dietary Ingredient|url=http://www.nutraceuticalsworld.com/contents/view_online-exclusives/2016-09-20/fda-concludes-vinpocetine-ineligible-as-a-dietary-ingredient|website=Nutraceuticals World|publisher=Rodman Media|access-date=January 18, 2017|date=September 20, 2016}}</ref><ref name="NW_020317">{{cite magazine| vauthors = Schmitt R |title=Dubious doses|url=https://www.pressreader.com/usa/newsweek/20170203/282071981620035|access-date=September 24, 2017|magazine=]|date=February 3, 2017}}</ref> Despite this, vinpocetine remains widely available in dietary supplements often marketed as ].<ref name="DTA2015">{{cite journal | vauthors = Avula B, Chittiboyina AG, Sagi S, Wang YH, Wang M, Khan IA, Cohen PA | title = Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States | journal = Drug Testing and Analysis | volume = 8 | issue = 3–4 | pages = 334–343 | date = March 2016 | pmid = 26426301 | doi = 10.1002/dta.1853 | doi-access = free }}</ref><ref name="Mayo2015">{{cite journal | vauthors = Cohen PA | title = Vinpocetine: An Unapproved Drug Sold as a Dietary Supplement | journal = Mayo Clinic Proceedings | volume = 90 | issue = 10 | pages = 1455 | date = October 2015 | pmid = 26434971 | doi = 10.1016/j.mayocp.2015.07.008 | doi-access = free }}</ref><ref name="FTC070815"/><ref name="Erickson"/> |
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Vinpocetine does not fully support a benefit in either ] or ].<ref name="Szatmari2003">{{cite journal | vauthors = Szatmari SZ, Whitehouse PJ | title = Vinpocetine for cognitive impairment and dementia | journal = The Cochrane Database of Systematic Reviews | volume = 2003 | issue = 1 | pages = CD003119 | year = 2003 | pmid = 12535455 | pmc = 8406981 | doi = 10.1002/14651858.CD003119 }}</ref><ref name="Mayo2015" /><ref name="Bereczki2009" /> As of 2003, three controlled ]s had tested "older adults with memory problems".<ref name="McDaniel2003">{{cite journal | vauthors = McDaniel MA, Maier SF, Einstein GO | title = "Brain-specific" nutrients: a memory cure? | journal = Nutrition | volume = 19 | issue = 11–12 | pages = 957–975 | year = 2003 | pmid = 14624946 | doi = 10.1016/S0899-9007(03)00024-8 }}</ref> |
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Vinpocetine has also been studied for the prevention and recovery of acquired hearing loss in a phase II, longitudinal and prospective open clinical study on humans.<ref>{{cite journal | vauthors = Gutiérrez-Farfán I, Reyes-Legorreta C, Solís-Olguín M, Alatorre-Miguel E, Verduzco-Mendoza A, Durand-Rivera A | title = Evaluation of vinpocetine as a therapy in patients with sensorineural hearing loss: A phase II, open-label, single-center study | journal = Journal of Pharmacological Sciences | volume = 145 | issue = 4 | pages = 313–318 | date = April 2021 | pmid = 33712282 | doi = 10.1016/j.jphs.2021.01.010 | doi-access = free }}</ref> |
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==Side effects== |
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Use during pregnancy may harm the baby or result in ].<ref name="FDA2019Preg">{{cite web | author = Office of the Commissioner |date=3 June 2019|title=Statement on warning for women of childbearing age about possible safety risks of dietary supplements containing vinpocetine|url=https://www.fda.gov/news-events/press-announcements/statement-warning-women-childbearing-age-about-possible-safety-risks-dietary-supplements-containing|access-date=5 June 2019|website=FDA|language=en}}</ref> |
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Adverse effects of vinpocetine include flushing, nausea, dizziness, dry mouth, transient hypo- and hyper-tension, headaches, heartburn, and decreased blood pressure.<ref name="DTA2015" /><ref name="NTP">{{cite web |author1=National Toxicology Program |author-link=National Toxicology Program |title=Chemical Information Review Document for Vinpocetine (CAS No. 42971-09-5) |url=https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/vinpocetine091613_508.pdf |publisher=] |access-date=December 28, 2018 |date=September 2013}}</ref> FDA issued a statement in 2019 warning that "vinpocetine may cause a miscarriage or harm fetal development".<ref>{{Cite web|url=https://www.fda.gov/news-events/press-announcements/statement-warning-women-childbearing-age-about-possible-safety-risks-dietary-supplements-containing|title=Statement on warning for women of childbearing age about possible safety risks of dietary supplements containing vinpocetine | author = Office of the Commissioner |date=2019-06-03|website=FDA|language=en|access-date=2019-06-04}}</ref> |
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==Mechanism of action== |
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Vinpocetine’s ] has been postulated to involve three potential effects: blockage of ], reduction of cellular calcium influx, and ] activity.<ref name="Bereczki2009">{{cite journal | vauthors = Bereczki D, Fekete I | title = Vinpocetine for acute ischaemic stroke | journal = The Cochrane Database of Systematic Reviews | volume = 2008 | issue = 1 | pages = CD000480 | date = January 2008 | pmid = 18253980 | pmc = 7034523 | doi = 10.1002/14651858.CD000480.pub2 }}</ref> Studies have also suggested that vinpocetine can inhibit ] in isolated rabbit aorta;<ref>{{cite journal | vauthors = Hagiwara M, Endo T, Hidaka H | title = Effects of vinpocetine on cyclic nucleotide metabolism in vascular smooth muscle | journal = Biochemical Pharmacology | volume = 33 | issue = 3 | pages = 453–457 | date = February 1984 | pmid = 6322804 | doi = 10.1016/0006-2952(84)90240-5 }}</ref> inhibit ] ], preventing ] degradation and the following translocation of ] to the cell nucleus;<ref name="Jeon">{{cite journal | vauthors = Jeon KI, Xu X, Aizawa T, Lim JH, Jono H, Kwon DS, Abe J, Berk BC, Li JD, Yan C | title = Vinpocetine inhibits NF-kappaB-dependent inflammation via an IKK-dependent but PDE-independent mechanism | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 107 | issue = 21 | pages = 9795–9800 | date = May 2010 | pmid = 20448200 | pmc = 2906898 | doi = 10.1073/pnas.0914414107 | doi-access = free }}</ref><ref name="Medina">{{cite journal | vauthors = Medina AE | title = Vinpocetine as a potent antiinflammatory agent | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 107 | issue = 22 | pages = 9921–9922 | date = June 2010 | pmid = 20495091 | pmc = 2890434 | doi = 10.1073/pnas.1005138107 | doi-access = free | bibcode = 2010PNAS..107.9921M }}</ref> and increase ], a metabolic breakdown product of ], in isolated striatal nerve endings of rats.<ref name=pmid11478921>{{cite journal | vauthors = Trejo F, Nekrassov V, Sitges M | title = Characterization of vinpocetine effects on DA and DOPAC release in striatal isolated nerve endings | journal = Brain Research | volume = 909 | issue = 1–2 | pages = 59–67 | date = August 2001 | pmid = 11478921 | doi = 10.1016/S0006-8993(01)02621-X | s2cid = 38990597 }}</ref> |
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==Dietary supplement== |
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The inclusion of vinpocetine in ] in the U.S. has come under scrutiny due to the lack of defined dosage parameters, unproven short- and long-term benefits, and risks to human health.<ref name="French">{{cite journal | vauthors = French JM, King MD, McDougal OM | title = Quantitative Determination of Vinpocetine in Dietary Supplements | journal = Natural Product Communications | volume = 11 | issue = 5 | pages = 607–609 | date = May 2016 | doi = 10.1177/1934578X1601100512 | pmid = 27319129 | pmc = 5345962 }}</ref> In the U.S., vinpocetine supplements are marketed as sports supplements, brain enhancers, and weight loss supplements.<ref name="Mayo2015"/> |
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A 2015 analysis of 23 brands of vinpocetine dietary supplements sold at ] and ] retail stores reported widespread labeling errors.<ref name="Newsweek_011217"/> Only 6 of the 23 supplement labels (26%) provided consumers with accurate dosages of vinpocetine (ranging from 0.3 to 32 mg per recommended daily serving), while 6 of 23 (26%) contained no vinpocetine at all, despite their labels claiming that the ingredient was in them.<ref name="Mayo2015"/><ref name="DTA2015"/> In total, 9 of the 23 products tested were mislabeled, and 17 of 23 (74%) did not provide any information on the quantity of vinpocetine.<ref name="DTA2015"/> |
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In response to the study, then-senator ], while at the time serving as the top ] on the ], urged the FDA to suspend sales of vinpocetine supplements and asked 10 retailers to voluntarily stop selling vinpocetine products. McCaskill stated: "The way we regulate these supplements isn’t working—and it’s putting the lives and well-being of consumers at risk. We’ve seen products with false labels, tainted ingredients, wildly illegal claims, and, now, products containing synthesized ingredients that are classified as prescription drugs in other countries."<ref name="Erickson">{{cite journal | vauthors = Erickson BE |title=Vinpocetine: drug or dietary supplement? |journal=Chemical & Engineering News |date=October 31, 2016 |volume=94 |issue=43 |pages=16–17 |url=https://cen.acs.org/content/cen/articles/94/i43/Vinpocetine-drug-dietary-supplement.html |access-date=December 28, 2018 |issn=0009-2347}}</ref> |
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===Lawsuits=== |
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Procera AVH is a dietary supplement containing undisclosed amounts of vinpocetine in combination with ] and ].<ref name="TBT070915">{{cite news | vauthors = McGrory K |title=Tampa diet supplement firm pays $1.4 million settlement over 'brain power' pill claims |url=https://www.tampabay.com/news/health/tampa-distributor-related-companies-face-14-million-penalty-for-brain/2236830 |access-date=January 1, 2019 |newspaper=] |date=July 9, 2015}}</ref><ref name="SBM091812">{{cite web | vauthors = Hall H |title=Procera AVH: A Pill to Restore Memory |url=https://sciencebasedmedicine.org/procera-avh-a-pill-to-restore-memory/ |website=] |access-date=January 1, 2019 |date=September 18, 2012}}</ref> In 2012, manufacturer Brain Research Labs (BRL) agreed to pay $500,000 to settle a class action lawsuit which alleged that the company had falsely marketed Procera AVH as capable of improving brain function, in violation of the Consumer Fraud Act.<ref name="OCR070615">{{cite news | vauthors = Almada B |title=False claims for brain supplement draw $152 million penalty from FTC |url=https://www.ocregister.com/2015/07/06/false-claims-for-brain-supplement-draw-152-million-penalty-from-ftc/ |access-date=January 1, 2019 |newspaper=] |date=July 6, 2015}}</ref> |
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In July 2015, the ] (FTC) ruled that marketing claims for Procera AVH, which promoted the product as a “solution” to memory loss and cognitive decline, were false, misleading, unsubstantiated, and in violation of the FTC Act.<ref name="OCR070615"/><ref name="FTC070815">{{cite web |title=Supplement Marketers Will Relinquish $1.4 Million to Settle FTC Deceptive Advertising Charges |newspaper=Federal Trade Commission |url=https://www.ftc.gov/news-events/press-releases/2015/07/supplement-marketers-will-relinquish-14-million-settle-ftc |publisher=] |access-date=January 1, 2019 |date=July 8, 2015}}</ref><ref name="NLR072015">{{cite magazine |title=Procera AVH Marketers Can Forget About Claiming to Reverse Memory Loss |date=July 30, 2015 |url=https://www.natlawreview.com/article/procera-avh-marketers-can-forget-about-claiming-to-reverse-memory-loss |access-date=1 January 2019 |magazine=]}}</ref><ref name="NPI070815">{{cite web | vauthors = Myers S |title=Memory Supplement Marketers Settle FTC Case for $150M |url=https://www.naturalproductsinsider.com/claims/memory-supplement-marketers-settle-ftc-case-150m |website= Natural Products Insider |access-date=1 January 2019 |date=July 8, 2015}}</ref> BRL and its affiliated companies Brain Power Partners, Brain Power Founders, and MedHealth Direct (all based in ]) were fined $91 million. KeyView Labs, the ]-based company that purchased BRL in 2012, was fined $61 million.<ref name="OCR070615"/><ref name="NLR072015"/><ref name="FTC070815"/><ref name="NPI070815"/> Also named in the FTC complaint were George Reynolds (aka Josh Reynolds), founder and chief science officer of BRL, and John Arnold, the sole officer and employee of MedHealth. The FTC complaint charged Reynolds with making deceptive expert endorsements for Procera AVH.<ref name="TBT070915"/><ref name="OCR070615"/><ref name="NLR072015"/><ref name="FTC070815"/><ref name="NPI070815"/> The defendants in the case ultimately agreed to pay $1.4 million to settle the allegations of deceptive advertising brought by the FTC and California law enforcement officials. In addition, a permanent injunction barred the defendants from making similar deceptive claims about Procera AVH in the future and from misrepresenting the existence, results, or conclusions of any scientific study.<ref name="NLR072015"/><ref name="FTC070815"/> |
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== References == |
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{{Reflist}} |
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{{Phosphodiesterase inhibitors}} |
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