Clorgiline

Clorgiline

Clinical data
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name N-[3-(2,4-dichlorophenoxy)propyl]-N-methyl-prop-2-yn-1-amine
CAS Number	17780-72-2  Y
PubChem CID	4380
IUPHAR/BPS	6636
DrugBank	DB04017  Y
ChemSpider	4227  Y
UNII	LYJ16FZU9Q
KEGG	D03248  Y
ChEBI	CHEBI:3763  N
ChEMBL	ChEMBL8706  Y
CompTox Dashboard (EPA)	DTXSID3048445
Chemical and physical data
Formula	C13H15Cl2NO
Molar mass	272.17 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1cc(Cl)ccc1OCCCN(CC#C)C
InChI InChI=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 Y Key:BTFHLQRNAMSNLC-UHFFFAOYSA-N Y
NY  (what is this?)    (verify)

Clorgiline (INN), or clorgyline (BAN), is a monoamine oxidase inhibitor (MAOI) structurally related to pargyline which is described as an antidepressant. ^{[1] [2]} Specifically, it is an irreversible and selective inhibitor of monoamine oxidase A (MAO-A). ^[3] Clorgiline was never marketed, ^[1] but it has found use in scientific research. ^[4] It has been found to bind with high affinity to the σ₁ receptor (K_i = 3.2 nM) ^{[3] [5]} and with very high affinity to the I₂ imidazoline receptor (K_i = 40 pM). ^[6]

Unlike selegiline, clorgiline does not appear to be a monoaminergic activity enhancer (MAE). ^{[7] [8] [9] [10]}

Clorgiline is also a multidrug efflux pump inhibitor. ^[11] Holmes et al., 2012 reverse azole fungicide resistance using clorgiline, showing promise for its use in multiple fungicide resistance. ^[11]

References

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 304–. ISBN   978-1-4757-2085-3.
2. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 80–. ISBN   978-94-011-4439-1.
3. Stone TW (January 1993). Acetylcholine, Sigma Receptors, CCK and Eicosanoids, Neurotoxins. Taylor & Francis. pp. 124–. ISBN   978-0-7484-0063-8.
4. Murphy DL, Karoum F, Pickar D, Cohen RM, Lipper S, Mellow AM, et al. (1998). "Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (Clorgyline) or MAO-B (Selegiline and pargyline)". MAO — the Mother of all Amine Oxidases. Journal of Neural Transmission. Supplement. Vol. 52. pp. 39–48. doi:10.1007/978-3-7091-6499-0_5. ISBN   978-3-211-83037-6. PMID   9564606.
5. Yossef I (1994). Sigma Receptors. Academic Press. p. 84. ISBN   978-0-12-376350-1.
6. Piletz JE, Halaris A, Ernsberger PR (1994). "Psychopharmacology of imidazoline and alpha 2-adrenergic receptors: implications for depression". Critical Reviews in Neurobiology. 9 (1): 29–66 (43). PMID   8828003.
7. Shimazu S, Miklya I (May 2004). "Pharmacological studies with endogenous enhancer substances: β-phenylethylamine, tryptamine, and their synthetic derivatives". Prog Neuropsychopharmacol Biol Psychiatry. 28 (3): 421–427. doi:10.1016/j.pnpbp.2003.11.016. PMID   15093948.
8. Knoll J (1983). "Deprenyl (selegiline): the history of its development and pharmacological action". Acta Neurol Scand Suppl. 95: 57–80. doi: 10.1111/j.1600-0404.1983.tb01517.x . PMID   6428148.
9. Knoll J (May 1992). "The pharmacological profile of (-)deprenyl (selegiline) and its relevance for humans: a personal view". Pharmacology & Toxicology. 70 (5 Pt 1): 317–321. doi:10.1111/j.1600-0773.1992.tb00480.x. PMID   1608919.
10. Yen TT, Dalló J, Knoll J (1982). "The aphrodisiac effect of low doses of (-) deprenyl in male rats". Pol J Pharmacol Pharm. 34 (5–6): 303–308. PMID   6821215.
11. •  •Prasad R, Banerjee A, Shah AH (February 2017). "Resistance to antifungal therapies". Essays in Biochemistry. 61 (1). Portland Press (Biochemical Society): 157–166. CiteSeerX   10.1.1.1066.1806 . doi:10.1042/ebc20160067. PMID   28258238. S2CID   3414820.
    •  •Holmes AR, Keniya MV, Ivnitski-Steele I, Monk BC, Lamping E, Sklar LA, Cannon RD (March 2012). "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". Antimicrobial Agents and Chemotherapy. 56 (3). American Society for Microbiology: 1508–1515. doi:10.1128/aac.05706-11. PMC   3294898 . PMID   22203607. S2CID   21170509.