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Clorgiline

Summary

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 (Ki = 3.2 nM)[3][5] and with very high affinity to the I2 imidazoline receptor (Ki = 40 pM).[6]

Clorgiline
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • N-[3-(2,4-dichlorophenoxy)propyl]-N-methyl-prop-2-yn-1-amine
CAS Number
  • 17780-72-2 checkY
PubChem CID
  • 4380
IUPHAR/BPS
  • 6636
DrugBank
  • DB04017 checkY
ChemSpider
  • 4227 checkY
UNII
  • LYJ16FZU9Q
KEGG
  • D03248 checkY
ChEBI
  • CHEBI:3763 ☒N
ChEMBL
  • ChEMBL8706 checkY
CompTox Dashboard (EPA)
  • DTXSID3048445 Edit this at Wikidata
Chemical and physical data
FormulaC13H15Cl2NO
Molar mass272.17 g·mol−1
3D model (JSmol)
  • Interactive image
  • Clc1cc(Cl)ccc1OCCCN(CC#C)C
  • 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 checkY
  • Key:BTFHLQRNAMSNLC-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Clorgiline is also a multidrug efflux pump inhibitor.[7] Holmes et al., 2012 reverse azole fungicide resistance using clorgiline, showing promise for its use in multiple fungicide resistance.[7]

References edit

  1. ^ a b 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. ^ a b 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. ^ a b
    •  • 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.