Iprindole: Difference between revisions

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| verifiedrevid = 439569389
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| IUPAC_name = 3-(6,7,8,9,10,11-hexahydro- 5''H''-cycloocta[b]indol-5-yl)-''N'',''N''-dimethylpropan-1-amine
| IUPAC_name = 3-(6,7,8,9,10,11-hexahydro- 5''H''-cycloocta[b]indol-5-yl)-''N'',''N''-dimethylpropan-1-amine
| image = Iprindole-structure.png
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| width = 200
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| image2 = Iprindole3Dan.gif
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| StdInChIKey = PLIGPBGDXASWPX-UHFFFAOYSA-N
| StdInChIKey = PLIGPBGDXASWPX-UHFFFAOYSA-N
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              __NOTOC__
{{SI}}
{{CMG}}
==Overview==


'''Iprindole''' ('''Prondol''', '''Galatur''', '''Tertran'''), formerly known as '''pramindole''', is a [[tricyclic antidepressant]] (TCA) used in [[Europe]] for the treatment of [[major depressive disorder|depression]].<ref name="isbn0-7817-2468-6">{{cite book | author = Ayd, Frank J. | title = Lexicon of psychiatry, neurology, and the neurosciences | publisher = Lippincott-Williams & Wilkins | location = Philadelphia, Pa | year = 2000 | pages = | isbn = 0-7817-2468-6 | oclc = | doi = | url = http://books.google.com/?id=ea_QVG2BFy8C&lpg=PA531&dq=iprindole&pg=PA531#v=onepage&q=iprindole}}</ref><ref name="isbn0-412-54090-8">{{cite book | author = | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | pages = | isbn = 0-412-54090-8 | oclc = | doi = | url = http://books.google.com/?id=x2Su3GKCvtsC&lpg=PA3975&dq=iprindole%20prondol&pg=PA3975#v=onepage&q=}}</ref><ref name="isbn0-471-63107-8">{{cite book | author = Davison, Gerald C.; Hooley, Jill M.; Neale, John M. | title = Readings in abnormal psychology | publisher = Wiley | location = New York | year = 1989 | pages = | isbn = 0-471-63107-8 | oclc = | doi = | url = http://books.google.com/?id=jYhnhQ4X-e8C&lpg=PA186&dq=iprindole%20trimipramine&pg=PA186#v=onepage&q=iprindole}}</ref> It was introduced by [[Wyeth]] and has been used clinically since 1967.<ref name="pmid5548547">{{cite journal | author = | title = Jaundice from iprindole (Prondol) | journal = Drug and Therapeutics Bulletin | volume = 9 | issue = 3 | pages = 10–1 |date=January 1971 | pmid = 5548547 | doi = | url = http://dtb.bmj.com/content/9/3/10.abstract}}</ref> Notably, iprindole was the first [[second-generation antidepressant]] to be launched.<ref name="doi:10.1002/ddr.430030302">{{cite journal | author = Horn AS, Trace RC | title = Second generation antidepressants: The pharmacological and clinical significance of selected examples | journal = Drug Development Research | volume = 3 | issue = 3 | pages = 203–211 |date=January 1983 | doi = 10.1002/ddr.430030302 | url = http://www3.interscience.wiley.com/journal/109670310/abstract}}</ref>
'''Iprindole''' ('''Prondol''', '''Galatur''', '''Tertran'''), formerly known as '''pramindole''', is a [[tricyclic antidepressant]] (TCA) used in [[Europe]] for the treatment of [[major depressive disorder|depression]].<ref name="isbn0-7817-2468-6">{{cite book | author = Ayd, Frank J. | title = Lexicon of psychiatry, neurology, and the neurosciences | publisher = Lippincott-Williams & Wilkins | location = Philadelphia, Pa | year = 2000 | pages = | isbn = 0-7817-2468-6 | oclc = | doi = | url = http://books.google.com/?id=ea_QVG2BFy8C&lpg=PA531&dq=iprindole&pg=PA531#v=onepage&q=iprindole}}</ref><ref name="isbn0-412-54090-8">{{cite book | author = | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | pages = | isbn = 0-412-54090-8 | oclc = | doi = | url = http://books.google.com/?id=x2Su3GKCvtsC&lpg=PA3975&dq=iprindole%20prondol&pg=PA3975#v=onepage&q=}}</ref><ref name="isbn0-471-63107-8">{{cite book | author = Davison, Gerald C.; Hooley, Jill M.; Neale, John M. | title = Readings in abnormal psychology | publisher = Wiley | location = New York | year = 1989 | pages = | isbn = 0-471-63107-8 | oclc = | doi = | url = http://books.google.com/?id=jYhnhQ4X-e8C&lpg=PA186&dq=iprindole%20trimipramine&pg=PA186#v=onepage&q=iprindole}}</ref> It was introduced by [[Wyeth]] and has been used clinically since 1967.<ref name="pmid5548547">{{cite journal | author = | title = Jaundice from iprindole (Prondol) | journal = Drug and Therapeutics Bulletin | volume = 9 | issue = 3 | pages = 10–1 |date=January 1971 | pmid = 5548547 | doi = | url = http://dtb.bmj.com/content/9/3/10.abstract}}</ref> Notably, iprindole was the first [[second-generation antidepressant]] to be launched.<ref name="doi:10.1002/ddr.430030302">{{cite journal | author = Horn AS, Trace RC | title = Second generation antidepressants: The pharmacological and clinical significance of selected examples | journal = Drug Development Research | volume = 3 | issue = 3 | pages = 203–211 |date=January 1983 | doi = 10.1002/ddr.430030302 | url = http://www3.interscience.wiley.com/journal/109670310/abstract}}</ref>
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{{Antidepressants}}
{{Antidepressants}}
{{Adrenergics}}
{{Cholinergics}}
{{Histaminergics}}
{{Serotonergics}}
{{Tricyclics}}


[[Category:5-HT2 antagonists]]
 
[[Category:Drug]]
[[Category:Tricyclic antidepressants]]
[[Category:Tricyclic antidepressants]]
[[Category:Indoles]]
[[Category:Indoles]]

Latest revision as of 16:32, 20 August 2015

Iprindole
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category
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Routes of
administration		Oral
ATC code
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Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability?
MetabolismHepatic[1]
Elimination half-life52.5 hours[2]
ExcretionUrine, Feces[3]
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CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H28N2
Molar mass284.439 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Iprindole (Prondol, Galatur, Tertran), formerly known as pramindole, is a tricyclic antidepressant (TCA) used in Europe for the treatment of depression.[4][5][6] It was introduced by Wyeth and has been used clinically since 1967.[7] Notably, iprindole was the first second-generation antidepressant to be launched.[8]

Iprindole is unique compared to most other TCAs in that it is a relatively weak inhibitor of the reuptake of serotonin and norepinephrine and instead acts predominantly as an antagonist of 5-HT2 receptors, hence its classification as 'second-generation'.[9][10][11] Additionally, side effects of iprindole are much less prominent relative to other TCAs and it is well tolerated.[12] However, iprindole's efficacy may not be as great as other TCAs, especially in regards to anxiety relief.[9][13]

Availability

Iprindole was sold under the trade name Prondol by Wyeth in the United Kingdom and Ireland for the indication of major depressive disorder,[14] and has also been sold as Galatur and Tertran by Wyeth as well.[15]

It has been discontinued throughout the world.[citation needed]

Chemistry

On a structural level, iprindole differs from other TCAs in that it contains an indole nucleus, similarly to the heterocyclic antipsychotic oxypertine, and has an eight-membered and saturated third ring.[12][16]

Pharmacology

Iprindole acts as an antagonist (or inverse agonist) of the following receptors:

And as an inhibitor of the following transporters:

It has negligible affinity (>10,000 nM) for β-adrenergic and sigma receptors.[32][33][34][35]

Dosage

Iprindole is used in doses of 30–180 mg daily.[4][36]

Side effects

Anticholinergic side effects such as dry mouth and constipation are either greatly reduced in comparison to imipramine and most other TCAs or fully lacking with iprindole.[12] However, it still has potent antihistamine effects and therefore can produce sedation, though this is diminished relative to imipramine as well, perhaps due to iprindole lacking significant alpha-blocking properties.[13]

Contraindications

Iprindole has been associated with jaundice and hepatotoxicity and should not be taken by alcoholics or people with pre-existing liver disease.[7][37][38][39] If such symptoms are encountered iprindole should be discontinued immediately.

Interactions

Iprindole has been shown to be a potent inhibitor of the aromatic hydroxylation and/or N-dealkylation-mediated metabolism of many substances including, but not limited to octopamine, amphetamine, methamphetamine, fenfluramine, phenelzine, tranylcypromine, trimipramine, and fluoxetine, likely via inactivating cytochrome P450 enzymes.[1][40][41][42][43][44] It also inhibits its own degradation.[43]

On account of these interactions, caution should be used when combining iprindole with other drugs.[1] As an example, when administered with amphetamine or methamphetamine, iprindole increases their brain concentrations and prolongs their half-lives by 2- to 3-fold, strongly augmenting both their physiological effects and neurotoxicity in the process.[45][46][47]

Overdose

In overdose, iprindole is much less toxic than most other TCAs and is considered relatively benign.[48] For instance, between 1974 and 1985, only two deaths associated with iprindole were recorded in the United Kingdom, whereas 278 were reported for imipramine.[48] However, it should be noted that imipramine is prescribed much more often than iprindole, and for that reason this comparison is likely not entirely representative of iprindole's true capacity for fatality in overdose.

See also

References

  1. ↑ 1.0 1.1 1.2 Rotzinger S, Bourin M, Akimoto Y, Coutts RT, Baker GB (August 1999). = 0272-4340&volume = 19&page = 427 "Metabolism of some "second"- and "fourth"-generation antidepressants: iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine" Check |url= value (help) (PDF). Cellular and Molecular Neurobiology. 19 (4): 427–42. doi:10.1023/A:1006953923305. PMID 10379419.
  2. ↑ Caillé G, de Montigny C, Besner JG (1982). "Quantitation of iprindole in plasma by GLC". Biopharmaceutics & Drug Disposition. 3 (1): 11–7. doi:10.1002/bdd.2510030103. PMID 7082775.
  3. ↑ Sisenwine SF, Tio CO, Ruelius HW (April 1979). "The disposition of [14C]iprindole in man, dog, miniature swine, rhesus monkey and rat". Xenobiotica. 9 (4): 237–46. doi:10.3109/00498257909038726. PMID 113942.
  4. ↑ 4.0 4.1 Ayd, Frank J. (2000). Lexicon of psychiatry, neurology, and the neurosciences. Philadelphia, Pa: Lippincott-Williams & Wilkins. ISBN 0-7817-2468-6.
  5. ↑ Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
  6. ↑ Davison, Gerald C.; Hooley, Jill M.; Neale, John M. (1989). Readings in abnormal psychology. New York: Wiley. ISBN 0-471-63107-8.
  7. ↑ 7.0 7.1 "Jaundice from iprindole (Prondol)". Drug and Therapeutics Bulletin. 9 (3): 10–1. January 1971. PMID 5548547.
  8. ↑ Horn AS, Trace RC (January 1983). "Second generation antidepressants: The pharmacological and clinical significance of selected examples". Drug Development Research. 3 (3): 203–211. doi:10.1002/ddr.430030302.
  9. ↑ 9.0 9.1 Zis AP, Goodwin FK (September 1979). "Novel antidepressants and the biogenic amine hypothesis of depression. The case for iprindole and mianserin". Archives of General Psychiatry. 36 (10): 1097–1107. doi:10.1001/archpsyc.1979.01780100067006. PMID 475543.
  10. ↑ Jaramillo J, Greenberg R (February 1975). "Comparative pharmacological studies on butriptyline and some related standard tricyclic antidepressants". Canadian Journal of Physiology and Pharmacology. 53 (1): 104–12. doi:10.1139/y75-014. PMID 166748.
  11. ↑ Horn AS, Trace RC (July 1974). "Structure-activity relations for the inhibition of 5-hydroxytryptamine uptake by tricyclic antidepressants into synaptosomes from serotoninergic neurones in rat brain homogenates". British Journal of Pharmacology. 51 (3): 399–403. doi:10.1111/j.1476-5381.1974.tb10675.x. PMC 1776771. PMID 4451753.
  12. ↑ 12.0 12.1 12.2 Progress in medicinal chemistry - Google Books.
  13. ↑ 13.0 13.1 Rickels K, Chung HR, Csanalosi I, Sablosky L, Simon JH (September 1973). "Iprindole and imipramine in non-psychotic depressed out-patients". The British Journal of Psychiatry : the Journal of Mental Science. 123 (574): 329–39. doi:10.1192/bjp.123.3.329. PMID 4583430.
  14. ↑ Sean C. Sweetman (2009). Martindale: The Complete Drug Reference, 36th Edition. London: Pharmaceutical Press. ISBN 0-85369-840-6.
  15. ↑ "DrugFuture.com - Iprindole".
  16. ↑ Baxter BL, Gluckman MI (August 1969). "Iprindole: an antidepressant which does not block REM sleep". Nature. 223 (5207): 750–2. Bibcode:1969Natur.223..750B. doi:10.1038/223750a0. PMID 4308422.
  17. ↑ Wander TJ, Nelson A, Okazaki H, Richelson E (December 1986). "Antagonism by antidepressants of serotonin S1 and S2 receptors of normal human brain in vitro". European Journal of Pharmacology. 132 (2–3): 115–21. doi:10.1016/0014-2999(86)90596-0. PMID 3816971.
  18. ↑ 18.0 18.1 Pälvimäki EP, Roth BL, Majasuo H; et al. (August 1996). "Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor". Psychopharmacology. 126 (3): 234–40. doi:10.1007/BF02246453. PMID 8876023.
  19. ↑ 19.0 19.1 Darvesh AS, Shankaran M, Gudelsky GA (April 2002). "3,4-Methylenedioxymethamphetamine produces glycogenolysis and increases the extracellular concentration of glucose in the rat brain". The Journal of Pharmacology and Experimental Therapeutics. 301 (1): 138–44. doi:10.1124/jpet.301.1.138. PMID 11907167.
  20. ↑ 20.0 20.1 Bevan P, Bradshaw CM, Szabadi E (September 1975). "Effects of iprindole on responses of single cortical and caudate neurones to monoamines and acetylcholine". British Journal of Pharmacology. 55 (1): 17–25. doi:10.1111/j.1476-5381.1975.tb07605.x. PMC 1666724. PMID 1182344.
  21. ↑ 21.0 21.1 Nagayama H, Hingtgen JN, Aprison MH (July 1981). "Postsynaptic action by four antidepressive drugs in an animal model of depression". Pharmacology, Biochemistry, and Behavior. 15 (1): 125–30. doi:10.1016/0091-3057(81)90350-6. PMID 6974869.
  22. ↑ 22.0 22.1 22.2 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.
  23. ↑ García-Sevilla JA, Hollingsworth PJ, Smnith CB (September 1981). "Alpha 2-adrenoreceptors on human platelets: selective labelling by [3H]clonidine and [3H]yohimbine and competitive inhibition by antidepressant drugs". European Journal of Pharmacology. 74 (4): 329–41. doi:10.1016/0014-2999(81)90052-2. PMID 6271559.
  24. ↑ Kanba S, Richelson E (June 1984). "Histamine H1 receptors in human brain labelled with [3H]doxepin". Brain Research. 304 (1): 1–7. doi:10.1016/0006-8993(84)90856-4. PMID 6146381.
  25. ↑ Hall H, Ogren SO (February 1984). "Effects of antidepressant drugs on histamine-H1 receptors in the brain". Life Sciences. 34 (6): 597–605. doi:10.1016/0024-3205(84)90494-6. PMID 6141518.
  26. ↑ Onodera K, Ogura Y (January 1984). "Effects of histaminergic drugs on muricide induced by thiamine deficiency". Japanese Journal of Pharmacology. 34 (1): 15–21. doi:10.1254/jjp.34.15. PMID 6143844.
  27. ↑ Tsai BS, Yellin TO (November 1984). "Differences in the interaction of histamine H2 receptor antagonists and tricyclic antidepressants with adenylate cyclase from guinea pig gastric mucosa". Biochemical Pharmacology. 33 (22): 3621–5. doi:10.1016/0006-2952(84)90147-3. PMID 6150708.
  28. ↑ El-Fakahany E, Richelson E (January 1983). "Antagonism by antidepressants of muscarinic acetylcholine receptors of human brain". British Journal of Pharmacology. 78 (1): 97–102. doi:10.1111/j.1476-5381.1983.tb17361.x. PMC 2044798. PMID 6297650.
  29. ↑ Golds PR, Przyslo FR, Strange PG (March 1980). "The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors". British Journal of Pharmacology. 68 (3): 541–9. doi:10.1111/j.1476-5381.1980.tb14570.x. PMC 2044199. PMID 7052344.
  30. ↑ Weinstock M, Cohen D (December 1976). "Tricyclic antidepressant drugs as antagonists of muscarinic receptors in sympathetic ganglia". European Journal of Pharmacology. 40 (2): 321–8. doi:10.1016/0014-2999(76)90069-8. PMID 62672.
  31. ↑ 31.0 31.1 31.2 Tatsumi M, Groshan K, Blakely RD, Richelson E (December 1997). "Pharmacological profile of antidepressants and related compounds at human monoamine transporters". European Journal of Pharmacology. 340 (2–3): 249–58. doi:10.1016/S0014-2999(97)01393-9. PMID 9537821.
  32. ↑ Bylund DB, Snyder SH (July 1976). "Beta adrenergic receptor binding in membrane preparations from mammalian brain". Molecular Pharmacology. 12 (4): 568–80. PMID 8699.
  33. ↑ Ganry H, Bourin M (1988). "Is iprindole an indirect betamimetic drug?". Neuropsychobiology. 20 (4): 187–93. doi:10.1159/000118497. PMID 2908249.
  34. ↑ Ganry H, Bourin M (May 1993). "Has iprindole an alpha adrenergic activity?". Progress in Neuro-psychopharmacology & Biological Psychiatry. 17 (3): 435–51. doi:10.1016/0278-5846(93)90077-6. PMID 8097333.
  35. ↑ Largent BL, Gundlach AL, Snyder SH (August 1984). "Psychotomimetic opiate receptors labeled and visualized with (+)-[3H]3-(3-hydroxyphenyl)-N-(1-propyl)piperidine". Proceedings of the National Academy of Sciences of the United States of America. 81 (15): 4983–7. Bibcode:1984PNAS...81.4983L. doi:10.1073/pnas.81.15.4983. PMC 391617. PMID 6087359.
  36. ↑ Wing, Lorna; Wing, J. K. (1982). Psychoses of uncertain aetiology. Cambridge, UK: Cambridge University Press. ISBN 0-521-28438-4.
  37. ↑ Aronson, Jeffrey Kenneth (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. ISBN 0-444-53266-8.
  38. ↑ Ajdukiewicz AB, Grainger J, Scheuer PJ, Sherlock S (September 1971). "Jaundice due to iprindole". Gut. 12 (9): 705–8. doi:10.1136/gut.12.9.705. PMC 1411804. PMID 4106521.
  39. ↑ Clift AD (June 1971). "Allergy to iprindole (Prondole) with hepatotoxicity". British Medical Journal. 2 (5763): 712. doi:10.1136/bmj.2.5763.712. PMC 1796275. PMID 5556082.
  40. ↑ Sedlock ML, Ravitch J, Edwards DJ (August 1985). "The effects of imipramine and iprindole on the metabolism of octopamine in the rat". Neuropharmacology. 24 (8): 705–8. doi:10.1016/0028-3908(85)90002-4. PMID 3939325.
  41. ↑ Hegadoren KM, Baker GB, Coutts RT, Dewhurst WG (March 1991). "Interactions of iprindole with fenfluramine metabolism in rat brain and liver". Journal of Psychiatry & Neuroscience : JPN. 16 (1): 5–11. PMC 1188281. PMID 2049371.
  42. ↑ Yamamoto T, Takano R, Egashira T, Yamanaka Y (November 1984). "Metabolism of methamphetamine, amphetamine and p-hydroxymethamphetamine by rat-liver microsomal preparations in vitro". Xenobiotica. 14 (11): 867–75. doi:10.3109/00498258409151485. PMID 6506759.
  43. ↑ 43.0 43.1 Coutts RT, Hussain MS, Baker GB (December 1991). "Effect of iprindole on the metabolism of trimipramine in the rat". Journal of Psychiatry & Neuroscience : JPN. 16 (5): 272–5. PMC 1188365. PMID 1797102.
  44. ↑ Aspeslet LJ, Baker GB, Coutts RT, Torok-Both GA (1994). "The effects of desipramine and iprindole on levels of enantiomers of fluoxetine in rat brain and urine". Chirality. 6 (2): 86–90. doi:10.1002/chir.530060208. PMID 8204417.
  45. ↑ Fuller RW, Baker JC, Molloy BB (February 1977). "Biological disposition of rigid analogs of amphetamine". Journal of Pharmaceutical Sciences. 66 (2): 271–2. doi:10.1002/jps.2600660235. PMID 839428.
  46. ↑ Fuller RW, Hemrick-Luecke S (July 1980). "Long-lasting depletion of striatal dopamine by a single injection of amphetamine in iprindole-treated rats". Science. 209 (4453): 305–7. Bibcode:1980Sci...209..305F. doi:10.1126/science.7384808. PMID 7384808.
  47. ↑ Peat MA, Warren PF, Gibb JW (April 1983). "Effects of a single dose of methamphetamine and iprindole on the serotonergic and dopaminergic system of the rat brain". The Journal of Pharmacology and Experimental Therapeutics. 225 (1): 126–31. PMID 6187915.
  48. ↑ 48.0 48.1 Cassidy S, Henry J (October 1987). "Fatal toxicity of antidepressant drugs in overdose". British Medical Journal (Clinical Research Ed.). 295 (6605): 1021–4. doi:10.1136/bmj.295.6605.1021. PMC 1248068. PMID 3690249.

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