Vincamine
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447608674
| IUPAC_name = (3α,14β,16α)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
or
Methyl (15R,17S,19R)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraene-17-carboxylate
| image = (+)-Vincamine Structural Formula V2.svg
| width = 175
| tradename = Oxybral SR
| Drugs.com = {{drugs.com|international|vincamine}}
| pregnancy_category =
| legal_status =
| routes_of_administration = Oral
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1617-90-9
| ATC_prefix = C04
| ATC_suffix = AX07
| PubChem = 15376
| IUPHAR_ligand = 349
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB13374
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1165342
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 996XVD0JHT
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08677
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 14635
| smiles = O=C(OC)[C@]3(O)n1c4c(c2ccccc12)CCN5CCC[C@](C3)(CC)[C@@H]45
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RXPRRQLKFXBCSJ-GIVPXCGWSA-N
| C=21 | H=26 | N=2 | O=3
}}
Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor (lesser periwinkle), comprising about 25–65% of its indole alkaloids by weight. It can also be synthesized from related alkaloids.{{ cite encyclopedia | title = Indole Alkaloids | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | edition = Fifth | page = 393 | publisher = Wiley-VCH | year = 1985 | isbn = 3-527-20100-9 }}
Uses
Vincamine is sold in Europe as a prescription medicine for the treatment of primary degenerative and vascular dementia.{{cn|date=July 2019}} In the United States, it is permitted to be sold as a dietary supplement when labeled for use in adults for six months or less.{{cite web | url = https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/vincamine_508.pdf | title = Summary of Data for Chemical Selection: Vincamine | work = National Toxicology Program | publisher = U.S. Department of Health and Human Services }} Most common preparations are in the sustained release tablet forms.
Chemistry
=Synthesis=
Tabersonine can be used for semi-synthesis of vincamine.{{cite journal|url=https://www.erowid.org/plants/voacanga_africana/voacanga_africana_info1.shtml|journal=Agricultural University Wageningen Papers|issn=0169-345X|volume=85|issue=3|year=1985|title=Voacanga, (Apocynaceae), a review of taxonomy, phytochemistry, ethnobotany and pharmacology| vauthors = Leeuwenberg AJ |author1-link=Anthonius Josephus Maria Leeuwenberg}}
=Derivatives=
Vinpocetine is a synthetic derivative of vincamine used for cerebrovascular diseases and as dietary supplement.{{Cite journal | url=https://www.fda.gov/food/information-select-dietary-supplement-ingredients-and-other-substances/vinpocetine-dietary-supplements |title = Vinpocetine in Dietary Supplements|journal = FDA|date = 2019-06-03}} Vincamine derivatives have been also studied as anti addictive{{cite journal |vauthors=Norwood VM, Brice-Tutt AC, Eans SO, Stacy HM, Shi G, Ratnayake R, Rocca JR, Abboud KA, Li C, Luesch H, McLaughlin JP, Huigens RW |title=Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity |journal=Journal of Medicinal Chemistry |volume=63 |issue=10 |pages=5119–5138 |date=May 2020 |pmid=31913038 |pmc=7324933 |doi=10.1021/acs.jmedchem.9b01924 |url= |issn=}} and antidiabetic{{cite journal |vauthors=Wang J, Lv X, Xu J, Liu X, Du T, Sun G, Chen J, Shen X, Wang J, Hu L |title=Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic β-cells protective agents for the treatment of type 2 diabetes mellitus |journal=European Journal of Medicinal Chemistry |volume=188 |issue= |pages=111976 |date=February 2020 |pmid=31918073 |doi=10.1016/j.ejmech.2019.111976 |s2cid=210133217 |url= |issn=}} agents.
Research
It may have nootropic effects. It has been investigated as novel anticancer drug.{{cite journal |vauthors=Al-Rashed S, Baker A, Ahmad SS, Syed A, Bahkali AH, Elgorban AM, Khan MS |title=Vincamine, a safe natural alkaloid, represents a novel anticancer agent |journal=Bioorganic Chemistry |volume=107 |issue= |pages=104626 |date=February 2021 |pmid=33450545 |doi=10.1016/j.bioorg.2021.104626 |s2cid=231624167 |url= |issn=}}
Concerns over long-term use have been documented by the US National Toxicology Program.{{cite web
|title=Vincamine Dietary Supplements 1617-90-9 - National Toxicology Program|url=https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/chem_background/exsumpdf/vincamine_508.pdf |website=National Institute of Environmental Health Sciences |access-date=4 December 2023}}
See also
References
{{reflist}}
External links
- {{cite web | url = http://www.mpbio.com/includes/msds/ansi/en/158295-EN-ANSI.pdf | title = Vincamine MSDS | access-date = 2012-01-30 | archive-url = https://web.archive.org/web/20150608110220/http://www.mpbio.com/includes/msds/ansi/en/158295-EN-ANSI.pdf | archive-date = 2015-06-08 | url-status = dead }}
- {{cite web | url = https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/vincamine_508.pdf | work = Summary of Data for Chemical Selection | title = Vincamine - 1617-90-9 | author = Chemical Selection Working Group | publisher = NIH - United States National Institutes of Health | access-date = 2007-04-23 | archive-url = https://web.archive.org/web/20111021222436/http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Vincamine.pdf | archive-date = 2011-10-21 | url-status = live }}
{{Peripheral vasodilators}}