View source for Clorgiline

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443677087
| IUPAC_name = ''N''-[3-(2,4-dichlorophenoxy)propyl]-''N''-methyl-prop-2-yn-1-amine
| image = Clorgiline.svg
| width = 250px

<!--Clinical data-->
| tradename = 
| pregnancy_category = 
| legal_status = Uncontrolled
| routes_of_administration = 

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 

<!--Identifiers-->
| IUPHAR_ligand = 6636
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 17780-72-2
| ATC_prefix = none
| ATC_suffix = 
| PubChem = 4380
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04017
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 3763
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4227
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LYJ16FZU9Q
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03248
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 8706

<!--Chemical data-->
| C=13 | H=15 | Cl=2 | N=1 | O=1
| SMILES = Clc1cc(Cl)ccc1OCCCN(CC#C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H15Cl2NO/c1-3-7-16(2)8-4-9-17-13-6-5-11(14)10-12(13)15/h1,5-6,10H,4,7-9H2,2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BTFHLQRNAMSNLC-UHFFFAOYSA-N
}}

'''Clorgiline''' ([[International Nonproprietary Name|INN]]), or '''clorgyline''' ([[British Approved Name|BAN]]), is a [[monoamine oxidase inhibitor]] (MAOI) structurally related to [[pargyline]] which is described as an [[antidepressant]].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA304|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=304–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |url= https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA80 |date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=80–}}</ref> Specifically, it is an [[irreversible inhibition|irreversible]] and [[binding selectivity|selective]] [[enzyme inhibitor|inhibitor]] of [[monoamine oxidase A]] (MAO-A).<ref name="Stone1993">{{cite book| vauthors = Stone TW |title=Acetylcholine, Sigma Receptors, CCK and Eicosanoids, Neurotoxins|url=https://books.google.com/books?id=0xmt5kSpJEcC&pg=PA124|date=January 1993|publisher=Taylor & Francis|isbn=978-0-7484-0063-8|pages=124–}}</ref> Clorgiline was never marketed,<ref name="Elks2014" /> but it has found use in [[scientific research]].<ref name="MurphyKaroum1998">{{cite book | vauthors = Murphy DL, Karoum F, Pickar D, Cohen RM, Lipper S, Mellow AM, Tariot PN, Sunderland T | title = MAO — the Mother of all Amine Oxidases | chapter = Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (Clorgyline) or MAO-B (Selegiline and pargyline) | display-authors = 6  | volume = 52 | pages = 39–48 | year = 1998 | pmid = 9564606 | doi = 10.1007/978-3-7091-6499-0_5 | isbn = 978-3-211-83037-6 | series = Journal of Neural Transmission. Supplement }}</ref> It has been found to bind with high [[affinity (pharmacology)|affinity]] to the [[sigma-1 receptor|σ<sub>1</sub> receptor]] (K<sub>i</sub> = 3.2&nbsp;nM)<ref name="Stone1993" /><ref name="Itzhak1994">{{cite book| vauthors = Yossef I |title=Sigma Receptors|url=https://books.google.com/books?id=ndRqAAAAMAAJ|year=1994|publisher=Academic Press|isbn=978-0-12-376350-1|page=84}}</ref> and with very high affinity to the [[Imidazoline receptor|I<sub>2</sub> imidazoline receptor]] (K<sub>i</sub> = 40&nbsp;pM).<ref name="pmid8828003">{{cite journal | vauthors = Piletz JE, Halaris A, Ernsberger PR | title = Psychopharmacology of imidazoline and alpha 2-adrenergic receptors: implications for depression | journal = Critical Reviews in Neurobiology | volume = 9 | issue = 1 | pages = 29–66 (43) | date = 1994 | pmid = 8828003 | doi = | url = https://books.google.com/books?id=EP9FAQAAIAAJ }}</ref>

Unlike [[selegiline]], clorgiline does not appear to be a [[monoaminergic activity enhancer]] (MAE).<ref name="ShimazuMiklya2004">{{cite journal | vauthors = Shimazu S, Miklya I | title = Pharmacological studies with endogenous enhancer substances: β-phenylethylamine, tryptamine, and their synthetic derivatives | journal = Prog Neuropsychopharmacol Biol Psychiatry | volume = 28 | issue = 3 | pages = 421–427 | date = May 2004 | pmid = 15093948 | doi = 10.1016/j.pnpbp.2003.11.016 | url = }}</ref><ref name="Knoll1983">{{cite journal | vauthors = Knoll J | title = Deprenyl (selegiline): the history of its development and pharmacological action | journal = Acta Neurol Scand Suppl | volume = 95 | issue = | pages = 57–80 | date = 1983 | pmid = 6428148 | doi = 10.1111/j.1600-0404.1983.tb01517.x | url = | doi-access = free }}</ref><ref name="Knoll1992">{{cite journal | vauthors = Knoll J | title = The pharmacological profile of (-)deprenyl (selegiline) and its relevance for humans: a personal view | journal = Pharmacology & Toxicology | volume = 70 | issue = 5 Pt 1 | pages = 317–321 | date = May 1992 | pmid = 1608919 | doi = 10.1111/j.1600-0773.1992.tb00480.x }}</ref><ref name="YenDallóKnoll1982">{{cite journal | vauthors = Yen TT, Dalló J, Knoll J | title = The aphrodisiac effect of low doses of (-) deprenyl in male rats | journal = Pol J Pharmacol Pharm | volume = 34 | issue = 5-6 | pages = 303–308 | date = 1982 | pmid = 6821215 | doi = | url = }}</ref>

Clorgiline is also a [[multidrug resistance pump|multidrug efflux pump]] inhibitor.<ref name="Fungus" /> Holmes ''et al.'', 2012 reverse [[azole fungicide resistance]] using clorgiline, showing promise for its use in [[multiple fungicide resistance]].<ref name="Fungus">
   {{Unbulleted list citebundle
      |{{*}} {{cite journal | vauthors = Prasad R, Banerjee A, Shah AH | title = Resistance to antifungal therapies | journal = Essays in Biochemistry | volume = 61 | issue = 1 | pages = 157–166 | date = February 2017 | pmid = 28258238 | doi = 10.1042/ebc20160067 | publisher = [[Portland Press]] ([[Biochemical Society]]) | s2cid = 3414820 | citeseerx = 10.1.1.1066.1806 }}
      |{{*}} {{cite journal | vauthors = Holmes AR, Keniya MV, Ivnitski-Steele I, Monk BC, Lamping E, Sklar LA, Cannon RD | title = The monoamine oxidase A inhibitor clorgyline is a broad-spectrum inhibitor of fungal ABC and MFS transporter efflux pump activities which reverses the azole resistance of Candida albicans and Candida glabrata clinical isolates | journal = Antimicrobial Agents and Chemotherapy | volume = 56 | issue = 3 | pages = 1508–1515 | date = March 2012 | pmid = 22203607 | pmc = 3294898 | doi = 10.1128/aac.05706-11 | publisher = [[American Society for Microbiology]] | s2cid = 21170509 }}
   }}
</ref>

== References ==
{{Reflist|2}}

{{Imidazoline receptor modulators}}
{{Monoamine metabolism modulators}}
{{Sigma receptor modulators}}

[[Category:Abandoned drugs]]
[[Category:Propargyl compounds]]
[[Category:Amines]]
[[Category:Chloroarenes]]
[[Category:Imidazoline receptor modulators]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Phenol ethers]]
[[Category:Sigma agonists]]

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