Извор странице Himbacin

{{Drugbox-lat
| verifiedrevid = 400110105
| IUPAC_name = (3a''R'',4''R'',4a''S'',8a''R'',9a''S'')- 4-{(''E'')-[(2''R'',6''S'')- 1,6-dimethylpiperidin- 2-yl]vinyl}- 3-methyldecahydronaphtho[2,3-''c'']furan- 1(3''H'')-one
| image = Himbacine.svg
| width =
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4940913
| smiles = O=C3O[C@H]([C@@H]4[C@H](/C=C/[C@@H]1N(C)[C@@H](C)CCC1)[C@@H]2[C@H](CCCC2)C[C@H]34)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C22H35NO2/c1-14-7-6-9-17(23(14)3)11-12-19-18-10-5-4-8-16(18)13-20-21(19)15(2)25-22(20)24/h11-12,14-21H,4-10,13H2,1-3H3/b12-11+/t14-,15-,16+,17+,18-,19+,20-,21+/m0/s1
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| StdInChIKey = FMPNFDSPHNUFOS-LPJDIUFZSA-N
| CAS_number_Ref = {{cascite|correct|}}
| CAS_number = 6879-74-9
| ATC_prefix = none
| ATC_suffix = 
| PubChem = 6436265
| IUPHAR_ligand =
| ChEMBL_Ref =
| ChEMBL =
| DrugBank_Ref =
| DrugBank = 
| C = 22 | H = 35 | N = 1 | O = 2
| molecular_weight = 345.27 -{g/mol
}-| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 
| pregnancy_category= 
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| routes_of_administration = 
}}

'''Himbacin''' je [[alkaloid]] koji je izolovan iz kore Australijskih [[magnolija]]. Himbacin je bio sintetisan koristeći [[Diels-Alderova reakcija|Diels-Alderovu reakciju]] kao ključni korak.<ref name="pmid11674285">{{cite journal |author1=Chackalamannil S |author2=Davies RJ |author3=Wang Y |author4=''et al.'' |title=Total Synthesis of (+)-Himbacine and (+)-Himbeline |journal=J. Org. Chem. |volume=64 |issue=6 |pages=1932–1940 |year=1999 |pmid=11674285|doi=10.1021/jo981983}}</ref> Aktivnost himbacina kao [[antagonist (farmakologija)|antagonista]] [[Muskarinski acetilholinski receptor|muskarinskog receptora]], sa specifičnošću za [[muskarinski acetilholinski receptor M2]], mu je dala status obećavajuće početne tačke u istraživanjima [[Alchajmerova bolest|Alchajmerove bolesti]].<ref name="Malaska et al">{{cite journal |doi=10.1016/0960-894X(94)00459-S |vauthors=Malaska MJ, Fauq AH, Kozikowski AP, Aagaard PJ, McKinney M |title=Chemical Modification of Ring C of Himbacine:  Discovery of a Pharmacophoric Element for M2-Selectivity |journal= Bioorganic and Medicinal Chemistry Letters |volume=5 |issue=1 |pages=61–66 |year=1995}}</ref><ref name="pmid15225708">{{cite journal |vauthors=Chackalamannil S, Doller D, McQuade R, Ruperto V |title=Himbacine analogs as muscarinic receptor antagonists-effects of tether and heterocyclic variations |journal=Bioorganic and Medicinal Chemistry Letters |volume=14 |pages=3967–3970 |year=2004 |pmid=15225708 |doi=10.1016/j.bmcl.2004.05.047 |issue=15}}</ref>

Razvoj muskarinskih antagonista zasnovanih na himbacinu je bio neuspešan, ali je jedno analogno jedinjenje u [[kliničko ispitivanje|kliničkim ispitivanjima]] kao antagonist [[trombin]]skog receptora.<ref name="pmid18447380">{{cite journal |author1=Chackalamannil S |author2=Wang Y |author3=Greenlee WJ |author4='et al.'' |title=Discovery of a Novel, Orally Active Himbacine-Based Thrombin Receptor Antagonist (SCH 530348) with Potent Antiplatelet Activity |journal=J. Med. Chem. |volume=51 |pages=3061–3064 |year=2008 |pmid=18447380|doi=10.1021/jm800180e |issue=11}}</ref><ref name="urlIn Which I Hate A Wonder Drug. In the Pipeline:">{{cite web|url=http://pipeline.corante.com/archives/2008/05/13/in_which_i_hate_a_wonder_drug.php|title=Blog entry about Himbacine and its history in drug development|format=|work=|accessdate=|archive-url=https://web.archive.org/web/20110119205005/http://pipeline.corante.com/archives/2008/05/13/in_which_i_hate_a_wonder_drug.php|archive-date=19. 01. 2011|url-status=dead|df=}}</ref>

== Literatura ==
{{reflist|2}}

== Spoljašnje veze ==
{{Portal-lat|Medicina|Hemija}}
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