Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Butriptyline

From Wikipedia, the free encyclopedia
Atypical tricyclic antidepressant medication
Pharmaceutical compound
Butriptyline
Clinical data
Trade namesEvadyne, others
Other namesAY-62014[1]
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability?[3]
Protein binding>90%[3]
MetabolismHepatic (N-demethylation)
MetabolitesNorbutriptyline[3]
Eliminationhalf-life20 hours[3]
Identifiers
  • (±)-3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)-N,N,2-trimethylpropan-1-amine
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H27N
Molar mass293.454 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • c1cc3c(cc1)CCc2c(cccc2)C3CC(C)CN(C)C
  • InChI=1S/C21H27N/c1-16(15-22(2)3)14-21-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)21/h4-11,16,21H,12-15H2,1-3H3 checkY
  • Key:ALELTFCQZDXAMQ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Butriptyline, sold under the brand nameEvadyne among others, is atricyclic antidepressant (TCA) that has been used in theUnited Kingdom and several otherEuropean countries for the treatment ofdepression but appears to no longer be marketed.[1][4][5][6][7] Along withtrimipramine,iprindole, andamoxapine, it has been described as an "atypical" or"second-generation" TCA due to its relatively late introduction and atypicalpharmacology.[8][9] It was very little-used compared to other TCAs, with the number ofprescriptions dispensed only in the thousands.[10]

Medical uses

[edit]

Butriptyline was used in the treatment ofdepression.[11] It was usually used at dosages of 150–300 mg/day.[12]

Side effects

[edit]

Butriptyline is closely related toamitriptyline, and produces similar effects as other TCAs, but itsside effects likesedation are said to be reduced in severity and it has a lower risk ofinteractions with other medications.[6][7][10]

Butriptyline has potentantihistamine effects, resulting insedation andsomnolence.[13] It also has potentanticholinergic effects,[14] resulting in side effects likedry mouth,constipation,urinary retention,blurred vision, andcognitive/memory impairment.[13] The drug has relatively weak effects as analpha-1 blocker and has no effects as anorepinephrine reuptake inhibitor,[15][16] so is associated with little to noantiadrenergic andadrenergic side effects.[15][14][additional citation(s) needed]

Overdose

[edit]
Main article:Tricyclic antidepressant overdose

Pharmacology

[edit]

Pharmacodynamics

[edit]
See also:Pharmacology of antidepressants andTricyclic antidepressant § Binding profiles
Butriptyline[17]
SiteKi (nM)SpeciesRef
SERTTooltip Serotonin transporter1,360
4,300
10,000 (IC50Tooltip Half-maximal inhibitory concentration)		Human
Rat
Rat		[16]
[18]
[19]
NETTooltip Norepinephrine transporter5,100
990
1,700 (IC50)		Human
Rat
Rat		[16]
[18]
[19]
DATTooltip Dopamine transporter3,940
2,800
5,200 (IC50)		Human
Rat
Rat		[16]
[18]
[19]
5-HT1A7,000Human[20]
5-HT2A380Human[20]
5-HT2CNDNDND
α1570Human[15]
α24,800Human[15]
D2NDNDND
H11.1Human[15]
mAChTooltip Muscarinic acetylcholine receptor35Human[15]
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site.

In vitro, butriptyline is a strongantihistamine andanticholinergic, moderate5-HT2 andα1-adrenergic receptorantagonist, and very weak or negligiblemonoamine reuptake inhibitor.[15][20][16][19] These actions appear to confer a profile similar to that ofiprindole andtrimipramine withserotonin-blocking effects as the apparent predominant mediator of mood-lifting efficacy.[21][19][18]

However, in smallclinical trials, using similar doses, butriptyline was found to be similarly effective to amitriptyline andimipramine as an antidepressant, despite the fact that both of these TCAs are far stronger as both 5-HT2 antagonists andserotonin–norepinephrine reuptake inhibitors.[15][20][22] As a result, it may be that butriptyline has a differentmechanism of action, or perhaps functions as aprodrug in the body to ametabolite with differentpharmacodynamics.

Pharmacokinetics

[edit]

Therapeutic concentrations of butriptyline are in the range of 60–280 ng/mL (204–954 nmol/L).[23] Itsplasma protein binding is greater than 90%.[3]

Chemistry

[edit]

Butriptyline is atricyclic compound, specifically adibenzocycloheptadiene, and possesses threerings fused together with aside chain attached in itschemical structure.[24] Other dibenzocycloheptadiene TCAs includeamitriptyline,nortriptyline, andprotriptyline.[24] Butriptyline is ananalogue of amitriptyline with anisobutylside chain instead of apropylidene side chain.[10][25] It is atertiary amine TCA, with itsside chain-demethylated metabolite norbutriptyline being asecondary amine.[26][27] Other tertiary amine TCAs includeamitriptyline,imipramine,clomipramine,dosulepin (dothiepin),doxepin, andtrimipramine.[28][29] Thechemical name of butriptyline is 3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)-N,N,2-trimethylpropan-1-amine and itsfree base form has achemical formula of C21H27N with amolecular weight of 293.446 g/mol.[1] The drug has been used commercially both as the free base and as thehydrochloridesalt.[1][4] TheCAS Registry Number of the free base is 15686-37-0 and of the hydrochloride is 5585-73-9.[1][4]

History

[edit]

Butriptyline was developed byWyeth and introduced in theUnited Kingdom in either 1974 or 1975.[5][30][31]

Society and culture

[edit]

Generic names

[edit]

Butriptyline is theEnglish andFrenchgeneric name of the drug and itsINNTooltip International Nonproprietary Name,BANTooltip British Approved Name, andDCFTooltip Dénomination Commune Française, whilebutriptyline hydrochloride is itsBANMTooltip British Approved Name andUSANTooltip United States Adopted Name.[1][4][11] Its generic name inLatin isbutriptylinum, inGerman isbutriptylin, and inSpanish isbutriptylina.[4]

Brand names

[edit]

Butriptyline has been marketed under the brand namesEvadene,Evadyne,Evasidol, andCentrolese.[1][4][5]

Availability

[edit]

Butriptyline has been marketed inEurope, including in theUnited Kingdom,Belgium,Luxembourg,Austria, andItaly.[4][5]

References

[edit]
  1. ^abcdefgElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 201–.ISBN 978-1-4757-2085-3.
  2. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
  3. ^abcdeDörwald FZ (4 February 2013)."Dibenzazepines and Related Tricyclic Compounds".Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 313–.ISBN 978-3-527-64565-7.
  4. ^abcdefgSwiss Pharmaceutical Society (2000).Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers.ISBN 3-88763-075-0.Archived from the original on 2023-01-12. Retrieved2020-10-30.
  5. ^abcdWilliam Andrew Publishing (22 October 2013).Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 777–.ISBN 978-0-8155-1856-3.
  6. ^abHolenz J, Diaz JL, Buschmann H (16 April 2007)."Tricyclic and tetracyclic antidepressants". In Buschmann H (ed.).Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Wiley. pp. 180–.ISBN 978-3-527-31058-6.[permanent dead link]
  7. ^abPaykel ES (1992).Handbook of Affective Disorders. Guilford Press. pp. 339–.ISBN 978-0-89862-674-2.
  8. ^Sharma SS, Chawala P (18 November 2009)."Drug Therapy of Affective Disorders". In Seth A (ed.).Textbook Of Pharmacology. Elsevier India. pp. 119–.ISBN 978-81-312-1158-8.
  9. ^Bhattacharya A (2003)."Central Nervous System".Pharmacology (2nd ed.). Elsevier India. pp. 292–.ISBN 978-81-8147-009-6.
  10. ^abcAronson JK (2009).Meyler's Side Effects of Psychiatric Drugs. Elsevier. pp. 7, 18, 31.ISBN 978-0-444-53266-4.Archived from the original on 2024-07-26. Retrieved2017-08-13.
  11. ^abMorton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 58–.ISBN 978-94-011-4439-1.
  12. ^Paykel ES (29 October 1982)."Treatment for Affective Disorders". In Wing JK, Wing L (eds.).Handbook of Psychiatry: Volume 3, Psychoses of Uncertain Aetiology. CUP Archive. pp. 167–.ISBN 978-0-521-28438-7.
  13. ^abGillman PK (July 2007)."Tricyclic antidepressant pharmacology and therapeutic drug interactions updated".British Journal of Pharmacology.151 (6):737–748.doi:10.1038/sj.bjp.0707253.PMC 2014120.PMID 17471183.
  14. ^abMumenthaler M, van Zwieten PA, Farcot JM, eds. (1990)."Reactions to Antidepressant Drugs and Lithium Salts".Treatment of Chronic Pain: Possibilities, Limitations, and Long-term Follow-up. CRC Press. pp. 114–.ISBN 978-3-7186-5027-9.Archived from the original on 2024-07-26. Retrieved2017-08-13.
  15. ^abcdefghRichelson 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.doi:10.1016/S0022-3565(25)21446-X.PMID 6086881.
  16. ^abcdeTatsumi 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):249–258.doi:10.1016/s0014-2999(97)01393-9.PMID 9537821.
  17. ^Roth BL, Driscol J."PDSP Ki Database".Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health.Archived from the original on 2 December 2023. Retrieved14 August 2017.
  18. ^abcdRichelson E, Pfenning M (September 1984). "Blockade by antidepressants and related compounds of biogenic amine uptake into rat brain synaptosomes: most antidepressants selectively block norepinephrine uptake".European Journal of Pharmacology.104 (3–4):277–286.doi:10.1016/0014-2999(84)90403-5.PMID 6499924.
  19. ^abcdeRandrup A, Braestrup C (August 1977). "Uptake inhibition of biogenic amines by newer antidepressant drugs: relevance to the dopamine hypothesis of depression".Psychopharmacology.53 (3):309–314.doi:10.1007/BF00492370.PMID 408861.S2CID 8183053.
  20. ^abcdWander 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):115–121.doi:10.1016/0014-2999(86)90596-0.PMID 3816971.
  21. ^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):104–112.doi:10.1139/y75-014.PMID 166748.
  22. ^Stuart S (22 October 2013)."Tricyclic Antidepressants".Drugs in Psychiatric Practice. Elsevier. pp. 194–.ISBN 978-1-4831-9193-5.Archived from the original on 26 July 2024. Retrieved13 August 2017.
  23. ^Smith RN (6 December 2012)."Radioimmunoassay of Drugs in Body Fluids in a Forensic Context". In Maehly A, Williams RL (eds.).Forensic Science Progress. Springer Science & Business Media. pp. 24–.ISBN 978-3-642-73058-0.
  24. ^abRitsner MS (15 February 2013)."Appendix 2: List of Psychotropic Medications".Polypharmacy in Psychiatry Practice, Volume I: Multiple Medication Use Strategies. Springer Science & Business Media. pp. 270–271.ISBN 978-94-007-5805-6.
  25. ^Zavod RM, Knittel JJ (24 January 2012)."Drug Design and Relationship of Functional Groups to Pharmacological Activity". In Lemke TL, Williams DA (eds.).Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 604–.ISBN 978-1-60913-345-0.Archived from the original on 12 January 2023. Retrieved13 August 2017.
  26. ^Dawkins K, Manji HK, Potter WZ (20 September 1994)."Pharmacodynamics of Antidepressants". In Cutler NR, Sramek JJ, Narang PK (eds.).Pharmacodynamics and Drug Development: Perspectives in Clinical Pharmacology. John Wiley & Sons. pp. 160–.ISBN 978-0-471-95052-3.
  27. ^Baumann P, Hiemke C (23 February 2012)."Central Nervous System Drugs". In Anzenbacher P, Zanger UM (eds.).Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. pp. 302–.ISBN 978-3-527-64632-6.
  28. ^Anthony PK (2002)."Drugs Used in the Therapy of Depression".Pharmacology Secrets. Elsevier Health Sciences. pp. 39–.ISBN 1-56053-470-2.Archived from the original on 2023-01-10. Retrieved2017-08-16.
  29. ^Cowen P, Harrison P, Burns T (9 August 2012)."Drugs and Other Physical Treatments".Shorter Oxford Textbook of Psychiatry. OUP Oxford. pp. 532–.ISBN 978-0-19-162675-3.Archived from the original on 10 January 2023. Retrieved16 August 2017.
  30. ^Ghose K (11 November 2013)."Side-effects of tricyclic and related antidepressants". In Ghose K (ed.).Antidepressants for Elderly People. Springer. pp. 182–.ISBN 978-1-4899-3436-9.Archived from the original on 14 January 2023. Retrieved13 August 2017.
  31. ^Dawson AH (2004)."Cyclic Antidepressant Drugs". In Dart RC (ed.).Medical Toxicology. Lippincott Williams & Wilkins. pp. 836–.ISBN 978-0-7817-2845-4.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
Retrieved from "https://en.wikipedia.org/w/index.php?title=Butriptyline&oldid=1280963295"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp