Oxaprotiline

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Oxaprotiline
Oxaprotiline.svg
Clinical data
Routes of
administration
Oral
Legal status
Legal status
  • In general: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C20H23NO
Molar mass 293.40 g/mol
3D model (JSmol)
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Oxaprotiline (developmental code name C 49-802 BDA), also known as hydroxymaprotiline, is a norepinephrine reuptake inhibitor of the tetracyclic antidepressant (TeCA) family that is related to maprotiline. Though investigated as an antidepressant,[1] it was never marketed.

Pharmacology[edit]

Dextroprotiline acts as a potent norepinephrine reuptake inhibitor[2][3] and H1 receptor antagonist,[4] as well as a very weak α1-adrenergic receptor antagonist.[2][5] It has negligible affinity for the serotonin transporter,[2] dopamine transporter, α2-adrenergic receptor,[2][5] and muscarinic acetylcholine receptors.[5] Whether it has any antagonistic effects on the 5-HT2, 5-HT7, or D2 receptors like its relative maprotiline is unclear.

Levoprotiline acts as a selective H1 receptor antagonist, with no affinity for adrenaline, dopamine, muscarinic acetylcholine, or serotonin receptors, or any of the monoamine transporters.[2][3][4]

Chemistry[edit]

Oxaprotiline is a racemic compound composed of two isomers, R(−)- or levo- oxaprotiline (levoprotiline; CGP-12,103-A), and S(+)- or dextro- oxaprotiline (dextroprotiline; CGP-12,104-A). Both enantiomers are active, with the levo- form acting as an antihistamine and the dextro- form having a additional pharmacology (see above), but with both unexpectedly still retaining antidepressant effects.[6]

See also[edit]

References[edit]

  1. ^ Giedke H, Gaertner H, Breyer-Pfaff U, Rein W, Axmann D (1986). "Amitriptyline and oxaprotiline in the treatment of hospitalized depressive patients. Clinical aspects, psychophysiology, and drug plasma levels". European Archives of Psychiatry and Neurological Sciences. 235 (6): 329–338. doi:10.1007/bf00381001. PMID 3527706. 
  2. ^ a b c d e Waldmeier PC, Baumann PA, Hauser K, Maitre L, Storni A (June 1982). "Oxaprotiline, a noradrenaline uptake inhibitor with an active and an inactive enantiomer". Biochemical Pharmacology. 31 (12): 2169–76. doi:10.1016/0006-2952(82)90510-X. PMID 7115436. 
  3. ^ a b Reimann IW, Firkusny L, Antonin KH, Bieck PR (1993). "Oxaprotiline: enantioselective noradrenaline uptake inhibition indicated by intravenous amine pressor tests but not alpha 2-adrenoceptor binding to intact platelets in man". European Journal of Clinical Pharmacology. 44 (1): 93–5. doi:10.1007/BF00315288. PMID 8382162. 
  4. ^ a b Noguchi S, Inukai T, Kuno T, Tanaka C (June 1992). "The suppression of olfactory bulbectomy-induced muricide by antidepressants and antihistamines via histamine H1 receptor blocking". Physiology & Behavior. 51 (6): 1123–7. doi:10.1016/0031-9384(92)90297-F. PMID 1353628. 
  5. ^ a b c Richelson E, Nelson A (July 1984). "Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro". The Journal of Pharmacology and Experimental Therapeutics. 230 (1): 94–102. PMID 6086881. 
  6. ^ Noguchi S, Fukuda Y, Inukai T (May 1992). "Possible contributory role of the central histaminergic system in the forced swimming model". Arzneimittel-Forschung. 42 (5): 611–3. PMID 1530672.