Izvorni kod stranice Ciproheptadin

{{Drugbox-lat
| verifiedrevid = 460111355
| IUPAC_name = 4-(5''H''-dibenzo [a,d]ciklohepten-5-iliden)-1-metilpiperidin hidrohlorid
| image = Cyproheptadine.svg
| width =
| image2 = Cyproheptadine-Spartan-PM3-3D-balls.png
| width2 =

<!--Clinical data-->
| tradename = Periaktin
| Drugs.com = {{drugs.com-lat|monograph|cyproheptadine-hydrochloride}}
| MedlinePlus = a682541
| pregnancy_US = B
| legal_UK = P
| routes_of_administration = Oralno

<!--Pharmacokinetic data-->
| protein_bound = 96 do 99%
| metabolism = [[Jetra|Hepatički]] i [[bubreg|renalno]]
| elimination_half-life = 8,6 sata<ref name="pmid15083941">{{cite journal | author=Gunja N, Collins M, Graudins A | title = A comparison of the pharmacokinetics of oral and sublingual cyproheptadine | journal = Journal of Toxicology. Clinical Toxicology | volume = 42 | issue = 1 | pages=79–83 | year = 2004 | pmid = 15083941 | doi = | url = }}</ref>
| excretion = Fekalno i renalno

<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|}}
| CAS_number = 129-03-3
| CAS_supplemental = 969-33-5 ([[hidrohlorid]])
| ATC_prefix = R06
| ATC_suffix = AX02
| PubChem = 2913
| IUPHAR_ligand = 277
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank = DB00434
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2810
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2YHB6175DO
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07765
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4046
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 516

<!--Chemical data-->
| C = 21 | H = 21 | N = 1 
| molecular_weight = 287,398 g/mol
| smiles = c43\C(=C1/CCN(C)CC1)c2ccccc2\C=C/c3cccc4
| InChI = 1/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3
| InChIKey = JJCFRYNCJDLXIK-UHFFFAOYAW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JJCFRYNCJDLXIK-UHFFFAOYSA-N
}}

'''Ciproheptadin''' (''Periaktin'') je [[H1 antagonist|prva generacija]] [[antihistamin]]a sa dodatnim [[antiholinergik|antiholinergičnim]], [[Serotoninski antagonist|antiserotinergičnim]], i [[lokalni anestetik|lokalno anestetičkim]] svojstvima.<ref name="Goodman_Gilman">{{GoodmanGilman10th}}</ref><ref name=PDR>{{PhysiciansDeskReference2010}}</ref>

== Farmakologija ==
Ciproheptadin deluje kao [[antagonist (farmakologija)|antagonist]] (ili [[inverzni agonist]] u zavisnosti od aktivnog mesta) na sledećim [[receptor (biohemija)|receptorima]]:

* [[H1 receptor|H<sub>1</sub>]] (~0,05 nM)<ref name="pmid7925364">{{cite journal | author=Moguilevsky N, Varsalona F, Noyer M, ''et al.'' | title = Stable expression of human H1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene | journal = European Journal of Biochemistry / FEBS | volume = 224 | issue = 2 | pages=489–95 | year = 1994 | month = September | pmid = 7925364 | doi = 10.1111/j.1432-1033.1994.00489.x| url = http://onlinelibrary.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2956&date=1994&volume=224&issue=2&spage=489}}</ref> > [[5-HT2A receptor|5-HT<sub>2A</sub>]] (~2 nM)<ref name="pmid2898916">{{cite journal | author = Peroutka SJ | title = Antimigraine drug interactions with serotonin receptor subtypes in human brain | journal = Annals of Neurology | volume = 23 | issue = 5 | pages=500–4 | year = 1988 | month = May | pmid = 2898916 | doi = 10.1002/ana.410230512 | url =https://archive.org/details/sim_annals-of-neurology_1988-05_23_5/page/500}}</ref> ≈ [[5-HT2B receptor|5-HT<sub>2B</sub>]] (~1,5 nM)<ref name="pmid9225287">{{cite journal | author = Bonhaus DW, Weinhardt KK, Taylor M, ''et al.'' | title = RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist | journal = Neuropharmacology | volume = 36 | issue = 4–5 | pages=621–9 | year = 1997 | pmid = 9225287 | doi = 10.1016/S0028-3908(97)00049-X| url = }}</ref> ≈ [[5-HT2C receptor|5-HT<sub>2C</sub>]] (~2 nM)<ref name="pmid9225287" /> > [[muskarinski acetilholinski receptor|mACh]] ([[muskarinski acetilholinski receptor M1|M<sub>1</sub>]]-[[muskarinski acetilholinski receptor M5|M<sub>5</sub>]]; ~7-12 nM)<ref name="pmid8100134">{{cite journal | author = Stanton T, Bolden-Watson C, Cusack B, Richelson E | title = Antagonism of the five cloned human muscarinic cholinergic receptors expressed in CHO-K1 cells by antidepressants and antihistaminics | journal = Biochemical Pharmacology | volume = 45 | issue = 11 | pages=2352–4 | year = 1993 | month = June | pmid = 8100134 | doi = 10.1016/0006-2952(93)90211-E| url = }}</ref> ≈ [[D3 receptor|D<sub>3</sub>]] (~8 nM)<ref name="pmid9686407">{{cite journal | author = Toll L, Berzetei-Gurske IP, Polgar WE, ''et al.'' | title = Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications | journal = NIDA Research Monograph | volume = 178 | issue = | pages=440–66 | year = 1998 | month = March | pmid = 9686407 | doi = | url = }}</ref>

On ima slab, i verovatno zanemarljiv, [[afinitet (farmakologija)|afinitet]] za sledeća mesta vezivanja (K<sub>i</sub>):

* [[5-HT1A receptor|5-HT<sub>1A</sub>]] (~60-100 nM)<ref name="pmid2898916" /><ref name="pmid9686407" /> ≈ [[alfa-1 adrenergički receptor|α<sub>1</sub>-adrenergički]] (?? nM)<ref name="Dukhovich2005">{{Cite book | author=F. S. Dukhovich | title = Pharmacological aspects of molecular recognition | url = http://books.google.com/books?id=9hvuXVPepMQC&pg=PA117 | accessdate = 27 November 2011 | date = 15. 8. 2005. | publisher = Nova Publishers | isbn = 978-1-59454-676-1 | page = 117}}</ref> ≈ [[alfa-2 adrenergički receptor|α<sub>2</sub>-adrenergički]] (?? nM)<ref name="Dukhovich2005" /> > [[5-HT6 receptor|5-HT<sub>6</sub>]] (~135-150 nM)<ref name="pmid8522988">{{cite journal | author = Kohen R, Metcalf MA, Khan N, ''et al.'' | title = Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor | journal = Journal of Neurochemistry | volume = 66 | issue = 1 | pages=47–56 | year = 1996 | month = January | pmid = 8522988 | doi = 10.1046/j.1471-4159.1996.66010047.x| url = http://onlinelibrary.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0022-3042&date=1996&volume=66&issue=1&spage=47}}</ref><ref name="pmid8226867">{{cite journal | author = Bard JA, Zgombick J, Adham N, Vaysse P, Branchek TA, Weinshank RL | title = Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase | journal = The Journal of Biological Chemistry | volume = 268 | issue = 31 | pages = 23422–6 | year = 1993 | month = November | pmid = 8226867 | doi =  | url = http://www.jbc.org/cgi/pmidlookup?view=long&pmid=8226867 }}{{Dead link|date=September 2021 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> ≈ [[5-HT7 receptor|5-HT<sub>7</sub>]] (~125 nM)<ref name="pmid8226867" /> ≈ [[D1 receptor|D<sub>1</sub>]] (~115 nM)<ref name="pmid9686407" /> ≈ [[D2 receptor|D<sub>2</sub>]] (~115 nM)<ref name="pmid9686407" /> > [[5-HT3 receptor|5-HT<sub>3</sub>]] (~250 nM)<ref name="pmid9686407" /><ref name="pmid3352595">{{cite journal | author = Hoyer D, Neijt HC | title = Identification of serotonin 5-HT3 recognition sites in membranes of N1E-115 neuroblastoma cells by radioligand binding | journal = Molecular Pharmacology | volume = 33 | issue = 3 | pages = 303–9 | year = 1988 | month = March | pmid = 3352595 | doi =  | url = http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=3352595 }}{{Dead link|date=August 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> ≈ [[Norepinefrinski transporter|NET]] (~300 nM)<ref name="pmid11266163">{{cite journal | author = Runyon SP, Savage JE, Taroua M, Roth BL, Glennon RA, Westkaemper RB | title = Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene | journal = Bioorganic & Medicinal Chemistry Letters | volume = 11 | issue = 5 | pages=655–8 | year = 2001 | month = March | pmid = 11266163 | doi = 10.1016/S0960-894X(01)00023-3| url = http://linkinghub.elsevier.com/retrieve/pii/S0960894X01000233}}</ref>

Pored toga, ciproheptadin poseduje osobine [[blokator kalcijumskog kanala|blokatora kalcijumskog kanala]]<ref name="pmid6271323">{{cite journal | author=Lowe DA, Matthews EK, Richardson BP | title = The calcium antagonistic effects of cyproheptadine on contraction, membrane electrical events and calcium influx in the guinea-pig taenia coli | journal = British Journal of Pharmacology | volume = 74 | issue = 3 | pages=651–63 | year = 1981 | month = November | pmid = 6271323 | pmc = 2071752 | doi = | url =https://archive.org/details/sim_british-journal-of-pharmacology_1981-11_74_3/page/651}}</ref> i [[lokal anestetik|lokalnog anestetika]].<ref name="pmid428422">{{cite journal | author = Riccioppo Neto F | title = The local anesthetic effect of cyproheptadine on mammalian nerve fibres | journal = European Journal of Pharmacology | volume = 54 | issue = 3 | pages=203–7 | year = 1979 | month = March | pmid = 428422 | doi = 10.1016/0014-2999(79)90078-5| url = }}</ref>

== Reference ==
{{reflist|2}}

== Literatura ==
* {{Cite book |ref= harv|author=F. S. Dukhovich | title = Pharmacological aspects of molecular recognition | url = http://books.google.com/books?id=9hvuXVPepMQC&pg=PA117 | accessdate = 27 November 2011 |year=2005 | publisher = Nova Publishers | isbn = 978-1-59454-676-1 | page = 117}}

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

{{-}}
{{Sedativi}}
{{Adrenergici}}
{{Holinergici}}
<!--{{Dopaminergici}}-->
{{Histaminergici}}
{{Serotonergici}}

[[Kategorija:Serotoninski antagonisti]]
[[Kategorija:Piperidini]]
[[Kategorija:Dibenzociklohepteni]]
[[Kategorija:Antagonisti H1 receptora]]
[[Kategorija:5-HT7 antagonisti]]