Ketanserin

Last updated

Ketanserin
Ketanserin.png
Ketanserin 3D.png
Clinical data
Trade names Sufrexal
Other namesR-41468; R41468; R-41,468; KJK-945; R-49945; R49945
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 50% [1] [2]
Protein binding 95% (mainly albumin [2] [3]
Metabolism Extensive [3]
Metabolites • Ketanserin-ol [3]
Elimination half-life 10–29 hours [4] [1] [2]
Excretion Urine; 2% unchanged [3]
Identifiers
  • 3-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}quinazoline-2,4(1H,3H)-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.070.598 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H22FN3O3
Molar mass 395.434 g·mol−1
3D model (JSmol)
  • c1ccc2c(c1)c(=O)n(c(=O)[nH]2)CCN3CCC(CC3)C(=O)c4ccc(cc4)F
  • InChI=1S/C22H22FN3O3/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29/h1-8,16H,9-14H2,(H,24,29) Yes check.svgY
  • Key:FPCCSQOGAWCVBH-UHFFFAOYSA-N Yes check.svgY
   (verify)

Ketanserin, sold under the brand name Sufrexal, is an antihypertensive agent which is used to treat arterial hypertension and vasospastic disorders. [5] [6] [3] It is also used in scientific research as an antiserotonergic agent in the study of the serotonin system; specifically, the 5-HT2 receptor family. [7] The drug is taken by mouth. [6] [3]

Contents

Side effects of ketanserin include dizziness, tiredness, edema, dry mouth, weight gain, and QT interval prolongation. [6] Ketanserin acts as a selective antagonist of the serotonin 5-HT2A, α1-adrenergic, and histamine H1 receptors. [6] [8] [9] It also shows lower affinity for various other targets. [9]

Ketanserin was discovered at Janssen Pharmaceutica in 1980. [10] [11] It was the first serotonin 5-HT2A receptor antagonist to be discovered that showed selectivity over other serotonin receptors. [9] The drug is not available in the United States [1] and is mostly no longer marketed throughout the rest of the world. [12] [13]

Uses

Medical uses

Ketanserin is classified as an antihypertensive by the World Health Organization [14] and the National Institute of Health. [15]

It has been used to reverse pulmonary hypertension caused by protamine (which in turn was administered to reverse the effects of heparin overdose). [16]

The reduction in hypertension is not associated with reflex tachycardia. [17]

It has been used in cardiac surgery. [18]

A 2000 Cochrane Review found that, compared to placebo, ketanserin did not provide significant relief for people suffering from Raynaud's phenomenon attacks in the setting of progressive systemic sclerosis (an autoimmune disorder). While the frequency of the attacks was unaffected by ketanserin, there was a reduction in the duration of the individual attacks. However, due to the significant adverse effect burden, the authors concluded that ketanserin's utility for this indication is likely unbeneficial. [19]

Ketanserin is a selective 5-HT2A receptor antagonist that was initially developed as an anti-hypertensive medicine. However, now the drug is available as a topical gel formulation for treating wounds, burns, ulcers, and anal fissures. Its action is through the acceleration of epithelialization.

Research uses

With tritium (3H) radioactively labeled ketanserin is used as a radioligand for serotonin 5-HT2 receptors, e.g. in receptor binding assays and autoradiography. [20] This radio-labeling has enabled the study of serotonin 5-HT2A receptor distribution in the human brain. [21]

An autoradiography study of the human cerebellum has found an increasing binding of 3H-ketanserin with age (from below 50 femtomol per milligram tissue at around 30 years of age to over 100 above 75 years). [22] The same research team found no significant correlation with age in their homogenate binding study.

Ketanserin has also been used with carbon (11C) radioactively labeled NNC112 in order to image cortical D1 receptors without contamination by 5-HT2 receptors. [23]

Increasing research into the use of psychedelics as antidepressants has seen ketanserin used to both block the hallucinogenic experience, and to disentangle the specific cognitive effects of 5-HT2A activation. [24] Ketanserin has been found to block the psychedelic effects of psilocybin, [25] lysergic acid diethylamide (LSD), [26] [27] mescaline, [28] and ayahausca (dimethyltryptamine) [29] in clinical studies. [24] [30]

Pharmacology

Human molecular targets of ketanserin [31] [32] [9]
TargetAffinity (Ki)Ref(s)
α1A-adrenergic 6.3 nM [32]
α1B-adrenergic 6.3 nM [32]
α1D-adrenergic 16 nM [32]
α2A-adrenergic 372 nM (HT29) [31]
α2B-adrenergic 199 nM [31]
α2C-adrenergic 159 nM (opossum) [31]
5-HT1A 1,044–>10,000 nM [32] [31]
5-HT1B 2,515–6,300 nM [32] [31]
5-HT1D 32–>10,000 nM [32] [33] [34]
5-HT1E >10,000 nM [31]
5-HT1F 1.25–>10,000 nM [31]
5-HT2A 0.20–9.8 nM [32] [31]
5-HT2B 200–3,236 nM [32] [31]
5-HT2C 17–186 nM [32] [31]
5-HT3 >10,000 nM (rodent) [31]
5-HT4L 1,000 nM (rat) [31]
5-HT5A 20,000 nM [32] [31]
5-HT5B 1,000–1,585 nM (rodent) [31]
5-HT6 2,800 nM [31]
5-HT7 320–1,334 nM [32] [31]
D1 190–464 nM [31]
D2 >10,000 nM [31]
D3  ?
D4 148 nM (canine) [31]
D5 2,500 nM [32] [31]
H1 1.79 nM [31]
DAT >10,000 nM [31]
VMAT1 1,600 nM [32]
VMAT2 22–540 nM [32] [9]

Pharmacodynamics

Ketanserin is a high-affinity non-selective antagonist of 5-HT2 receptors in rodents, [31] [35] [33] In addition to the 5-HT2 receptors, ketanserin is also a high affinity antagonist for the H1 receptor. [36] It has also been found to block the vesicular monoamine transporter 2 (VMAT2). [37] [38]

Occupancy of the serotonin 5-HT2A receptor by ketanserin in humans has been studied. [39]

Pharmacokinetics

The bioavailability of ketanserin is 50%. [1] [2] The plasma protein binding of ketanserin is 95.0% and it is mainly bound to albumin. [2] The elimination half-life of ketanserin is 10 to 29 hours. [4] [1]

Chemistry

Synthesis

Thieme Patents: Sino: Revised: Analogues Ketanserin synthesis.svg
Thieme Patents: Sino: Revised: Analogues

Either 3-(2-Chloroethyl)quinazoline-2,4(1H,3H)-dione [5081-87-8] (1a), or alternatively 2,3-dihydro-[1,3]oxazolo[2,3-b]quinazolin-5-one [52727-44-3] (1b) can be used as starting material. Attachment of the sidechain to 4-(4-Fluorobenzoyl)piperidine [56346-57-7] (2) completes the synthesis of Ketanserin (3).

Society and culture

Names

Ketanserin is the generic name of the drug and its INN Tooltip International Nonproprietary Name, USAN Tooltip United States Adopted Name, BAN Tooltip British Approved Name. [12] It is also known by its major brand name Sufrexal and by its former developmental code names R-41468, KJK-945, and R-49945. [12]

See also

Related Research Articles

<span class="mw-page-title-main">Empathogen</span> Class of psychoactive drugs that produce empathic experiences

Empathogens or entactogens are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, relatedness, emotional openness—that is, empathy or sympathy—as particularly observed and reported for experiences with 3,4-methylenedioxymethamphetamine (MDMA). This class of drug is distinguished from the classes of hallucinogen or psychedelic, and amphetamine or stimulants. Major members of this class include MDMA, MDA, MDEA, MDOH, MBDB, 5-APB, 5-MAPB, 6-APB, 6-MAPB, methylone, mephedrone, GHB, αMT, and αET, MDAI among others. Most entactogens are phenethylamines and amphetamines, although several, such as αMT and αET, are tryptamines. When referring to MDMA and its counterparts, the term MDxx is often used. Entactogens are sometimes incorrectly referred to as hallucinogens or stimulants, although many entactogens such as ecstasy exhibit psychedelic or stimulant properties as well.

<span class="mw-page-title-main">5-HT receptor</span> Class of transmembrane proteins

5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission. The serotonin receptors are activated by the neurotransmitter serotonin, which acts as their natural ligand.

<span class="mw-page-title-main">5-Hydroxytryptophan</span> Chemical compound

5-Hydroxytryptophan (5-HTP), used medically as oxitriptan, is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitter serotonin.

5-HT<sub>2A</sub> receptor Subtype of serotonin receptor

The 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor (GPCR). The 5-HT2A receptor is a cell surface receptor, but has several intracellular locations.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

<span class="mw-page-title-main">Pipamperone</span> Antipsychotic drug

Pipamperone, sold under the brand name Dipiperon, is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia and as a sleep aid for depression. It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan. Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.

A serotonin antagonist, or serotonin receptor antagonist, is a drug used to inhibit the action of serotonin and serotonergic drugs at serotonin (5-HT) receptors.

5-HT<sub>2B</sub> receptor Mammalian protein found in Homo sapiens

5-Hydroxytryptamine receptor 2B (5-HT2B) also known as serotonin receptor 2B is a protein that in humans is encoded by the HTR2B gene. 5-HT2B is a member of the 5-HT2 receptor family that binds the neurotransmitter serotonin (5-hydroxytryptamine, 5-HT). Like all 5-HT2 receptors, the 5-HT2B receptor is Gq/G11-protein coupled, leading to downstream activation of phospholipase C.

<span class="mw-page-title-main">WAY-100635</span> Chemical compound

WAY-100635 is a piperazine drug and research chemical widely used in scientific studies. It was originally believed to act as a selective 5-HT1A receptor antagonist, but subsequent research showed that it also acts as potent full agonist at the D4 receptor. It is sometimes referred to as a silent antagonist at the former receptor. It is closely related to WAY-100135.

<span class="mw-page-title-main">Sarpogrelate</span> Chemical compound

Sarpogrelate is a drug which acts as an antagonist at the 5HT2A and 5-HT2B receptors. It blocks serotonin-induced platelet aggregation, and has applications in the treatment of many diseases including diabetes mellitus, Buerger's disease, Raynaud's disease, coronary artery disease, angina pectoris, and atherosclerosis.

<span class="mw-page-title-main">Quipazine</span> Chemical compound

Quipazine is a serotonergic drug of the piperazine group which is used in scientific research. It was originally intended as an antidepressant but never developed for medical use.

α-Methylserotonin Chemical compound

α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non-selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system.

<span class="mw-page-title-main">SDZ SER-082</span> Chemical compound

SDZ SER-082 is a drug which acts as a mixed antagonist for the 5-HT2B and 5-HT2C serotonin receptors, with good selectivity over other serotonin receptor subtypes and slight preference for 5-HT2C over 5-HT2B. It has been used in animal studies into the behavioural effects of the different 5-HT2 subtypes, and how they influence the effects of other drugs such as cocaine.

<span class="mw-page-title-main">SB-215505</span> Chemical compound

SB-215505 is a drug which acts as a potent and selective antagonist at the serotonin 5-HT2B receptor, with good selectivity over the related 5-HT2A and 5-HT2C receptors. It is used in scientific research into the function of the 5-HT2 family of receptors, especially to study the role of 5-HT2B receptors in the heart, and to distinguish 5-HT2B-mediated responses from those produced by 5-HT2A or 5-HT2C.

<span class="mw-page-title-main">Naphthylpiperazine</span> Chemical compound

1-(1-Naphthyl)piperazine (1-NP) is a drug which is a phenylpiperazine derivative. It acts as a non-selective, mixed serotonergic agent, exerting partial agonism at the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F receptors, while antagonizing the 5-HT2A, 5-HT2B, and 5-HT2C receptors. It has also been shown to possess high affinity for the 5-HT3, 5-HT5A, 5-HT6, and 5-HT7 receptors, and may bind to 5-HT4 and the SERT as well. In animals it produces effects including hyperphagia, hyperactivity, and anxiolysis, of which are all likely mediated predominantly or fully by blockade of the 5-HT2C receptor.

5-HT2C receptor agonists are a class of drugs that activate 5-HT2C receptors. They have been investigated for the treatment of a number of conditions including obesity, psychiatric disorders, sexual dysfunction and urinary incontinence.

<span class="mw-page-title-main">25CN-NBOH</span> Chemical compound

25CN-NBOH is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2014 at the University of Copenhagen. This compound is notable as one of the most selective agonist ligands for the 5-HT2A receptor yet discovered, with a pKi of 8.88 at the human 5-HT2A receptor and with 100x selectivity for 5-HT2A over 5-HT2C, and 46x selectivity for 5-HT2A over 5-HT2B. A tritiated version of 25CN-NBOH has also been accessed and used for more detailed investigations of the binding to 5-HT2 receptors and autoradiography.

<span class="mw-page-title-main">Pirenperone</span> Chemical compound

Pirenperone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name; developmental code names R-47456, R-50656) is a serotonin receptor antagonist described as an antipsychotic and tranquilizer which was never marketed. It is a relatively selective antagonist of the serotonin 5-HT2 receptors and has been used in scientific research to study the serotonin system. In the 1980s, the drug was found to block the effects of the lysergic acid diethylamide (LSD) in animals, and along with ketanserin, led to the elucidation of the 5-HT2A receptor as the biological mediator of the effects of serotonergic psychedelics.

A trip killer, or hallucinogen antidote, is a drug that aborts or reduces the effects of a hallucinogenic drug experience. As there are different types of hallucinogens that work in different ways, there are different types of trip killers. They can completely block or reduce the effects of hallucinogens or they can simply provide anxiety relief and sedation. Examples of trip killers, in the case of serotonergic psychedelics, include serotonin receptor antagonists, like antipsychotics and certain antidepressants, and benzodiazepines. Trip killers are sometimes used by recreational psychedelic users as a form of harm reduction to manage so-called bad trips, for instance difficult experiences with prominent anxiety. They can also be used clinically to manage effects of hallucinogens, like anxiety and psychomotor agitation, for instance in the emergency department.

References

  1. 1 2 3 4 5 Wolverton SE (8 March 2007). Comprehensive Dermatologic Drug Therapy (2 ed.). Elsevier Health Sciences. ISBN   978-1-4377-2070-9.
  2. 1 2 3 4 5 Hideya Saitō, Masaru Minami, eds. (1992). Antihypertensive Drugs Today. VSP. pp. 191–. ISBN   978-90-6764-140-1. OCLC   231351327.
  3. 1 2 3 4 5 6 Persson B, Heykants J, Hedner T (April 1991). "Clinical pharmacokinetics of ketanserin". Clin Pharmacokinet. 20 (4): 263–279. doi:10.2165/00003088-199120040-00002. PMID   2036747.
  4. 1 2 Cold GE, Dahl BL (11 November 2013). Topics in Neuroanaesthesia and Neurointensive Care: Experimental and Clinical Studies upon Cerebral Circulation, Metabolism and Intracranial Pressure. Springer Science & Business Media. pp. 193–. ISBN   978-3-662-04845-0. OCLC   1076237896.
  5. ↑ Symoens J (June 1990). "Ketanserin: a novel cardiovascular drug". Blood Coagul Fibrinolysis. 1 (2): 219–224. PMID   2130934.
  6. 1 2 3 4 Brogden RN, Sorkin EM (December 1990). "Ketanserin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in hypertension and peripheral vascular disease". Drugs. 40 (6): 903–949. doi:10.2165/00003495-199040060-00010. PMID   2079001.
  7. ↑ O'Donnell J, Ahuja GD (2005). Drug Injury: Liability, Analysis, and Prevention. Lawyers & Judges Publishing Company. pp. 304–. ISBN   978-0-913875-27-8.
  8. ↑ Awouters F (1985). "The pharmacology of ketanserin, the first selective serotonin S2‐antagonist". Drug Development Research. 6 (4). Wiley: 263–300. doi:10.1002/ddr.430060402. ISSN   0272-4391.
  9. 1 2 3 4 5 Casey AB, Cui M, Booth RG, Canal CE (June 2022). ""Selective" serotonin 5-HT2A receptor antagonists". Biochem Pharmacol. 200: 115028. doi:10.1016/j.bcp.2022.115028. PMC   9252399 . PMID   35381208. Since its discovery by Janssen Pharmaceuticals in 1981 (35), the quinazoline derivative ketanserin is among the most widely used tools for probing 5-HT2AR function in preclinical research (26–28, 36), and the sole antagonist used to delineate the 5-HT2AR-dependent effects of serotonergic psychedelics in humans (37–41). Although ketanserin was the first 5-HT2AR antagonist discovered that lacks high affinity for other serotonin and dopamine receptors, it is less appreciated that it has high affinity at several aminergic receptors, including α1A-, α1B-, α1D-adrenergic, and histamine H1 receptors (35, 42–44), as well as, moderate affinity at α2B-adrenergic and 5-HT2C receptors (Table 1). These off-target activities limit the utility of ketanserin as a specific tool for assessing 5-HT2AR activity.
  10. ↑ Healy D (1 July 2009). The Creation of Psychopharmacology. Harvard University Press. pp. 252–253. ISBN   978-0-674-03845-5.
  11. ↑ Schwartz H (August 1989). Breakthrough: the discovery of modern medicines at Janssen . Skyline Pub. Group. p.  74. ISBN   978-1-56019-100-1.
  12. 1 2 3 Schweizerischer Apotheker-Verein (2004). Index Nominum: International Drug Directory. Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 676. ISBN   978-3-88763-101-7 . Retrieved 8 October 2024.
  13. ↑ "Ketanserin (International database)". Drugs.com. 6 October 2024. Retrieved 8 October 2024.
  14. ↑ ATC/DDD Index
  15. ↑ Ketanserin
  16. ↑ van der Starre PJ, Solinas C (1996). "Ketanserin in the treatment of protamine-induced pulmonary hypertension". Texas Heart Institute Journal. 23 (4): 301–304. PMC   325377 . PMID   8969033.
  17. ↑ Hodsman NB, Colvin JR, Kenny GN (May 1989). "Effect of ketanserin on sodium nitroprusside requirements, arterial pressure control and heart rate following coronary artery bypass surgery". British Journal of Anaesthesia. 62 (5): 527–531. doi: 10.1093/bja/62.5.527 . PMID   2786422.
  18. ↑ Elbers PW, Ozdemir A, van Iterson M, van Dongen EP, Ince C (February 2009). "Microcirculatory Imaging in Cardiac Anesthesia: Ketanserin Reduces Blood Pressure But Not Perfused Capillary Density". Journal of Cardiothoracic and Vascular Anesthesia. 23 (1): 95–101. doi:10.1053/j.jvca.2008.09.013. PMID   19058975.
  19. ↑ Pope J, Fenlon D, Thompson A, Shea B, Furst D, Wells G, Silman A (2000). "Ketanserin for Raynaud's phenomenon in progressive systemic sclerosis". The Cochrane Database of Systematic Reviews. 1998 (2): CD000954. doi:10.1002/14651858.CD000954. PMC   7032891 . PMID   10796396.
  20. ↑ Eickhoff SB, Schleicher A, Scheperjans F, Palomero-Gallagher N, Zilles K (February 2007). "Analysis of neurotransmitter receptor distribution patterns in the cerebral cortex". NeuroImage. 34 (4): 1317–1330. doi:10.1016/j.neuroimage.2006.11.016. PMID   17182260. S2CID   23363050.
  21. ↑ Pazos A, Probst A, Palacios JM (April 1987). "Serotonin receptors in the human brain--IV. Autoradiographic mapping of serotonin-2 receptors". Neuroscience. 21 (1): 123–139. doi:10.1016/0306-4522(87)90327-7. PMID   3601071. S2CID   23711420.
  22. ↑ Eastwood SL, Burnet PW, Gittins R, Baker K, Harrison PJ (November 2001). "Expression of serotonin 5-HT(2A) receptors in the human cerebellum and alterations in schizophrenia". Synapse. 42 (2): 104–114. doi:10.1002/syn.1106. PMID   11574947. S2CID   40304220.
  23. ↑ Catafau AM, Searle GE, Bullich S, Gunn RN, Rabiner EA, Herance R, et al. (May 2010). "Imaging cortical dopamine D1 receptors using [11C]NNC112 and ketanserin blockade of the 5-HT 2A receptors". Journal of Cerebral Blood Flow and Metabolism. 30 (5): 985–993. doi:10.1038/jcbfm.2009.269. PMC   2949183 . PMID   20029452.
  24. 1 2 Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC   10851641 . PMID   37982394.
  25. ↑ Vollenweider FX, Vollenweider-Scherpenhuyzen MF, Bäbler A, Vogel H, Hell D (December 1998). "Psilocybin induces schizophrenia-like psychosis in humans via a serotonin-2 agonist action". NeuroReport. 9 (17): 3897–3902. doi:10.1097/00001756-199812010-00024. PMID   9875725.
  26. ↑ Holze F, Vizeli P, Ley L, Müller F, Dolder P, Stocker M, Duthaler U, Varghese N, Eckert A, Borgwardt S, Liechti ME (February 2021). "Acute dose-dependent effects of lysergic acid diethylamide in a double-blind placebo-controlled study in healthy subjects". Neuropsychopharmacology. 46 (3): 537–544. doi:10.1038/s41386-020-00883-6. PMC   8027607 . PMID   33059356.
  27. ↑ Becker AM, Klaiber A, Holze F, Istampoulouoglou I, Duthaler U, Varghese N, Eckert A, Liechti ME (February 2023). "Ketanserin Reverses the Acute Response to LSD in a Randomized, Double-Blind, Placebo-Controlled, Crossover Study in Healthy Participants". Int J Neuropsychopharmacol. 26 (2): 97–106. doi:10.1093/ijnp/pyac075. PMC   9926053 .
  28. ↑ Klaiber A, Schmid Y, Becker AM, Straumann I, Erne L, Jelusic A, Thomann J, Luethi D, Liechti ME (September 2024). "Acute dose-dependent effects of mescaline in a double-blind placebo-controlled study in healthy subjects". Transl Psychiatry. 14 (1): 395. doi:10.1038/s41398-024-03116-2. PMC   11442856 . PMID   39349427.
  29. ↑ Valle M, Maqueda AE, Rabella M, Rodríguez-Pujadas A, Antonijoan RM, Romero S, Alonso JF, Mañanas MÀ, Barker S, Friedlander P, Feilding A, Riba J (July 2016). "Inhibition of alpha oscillations through serotonin-2A receptor activation underlies the visual effects of ayahuasca in humans". Eur Neuropsychopharmacol. 26 (7): 1161–1175. doi:10.1016/j.euroneuro.2016.03.012. hdl: 2117/101863 . PMID   27039035.
  30. ↑ Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi: 10.1016/j.bpsc.2024.01.007 .
  31. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 NIMH Psychoactive Drug Screening Program
  32. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 "Ketanserin Ligand page". IUPHAR/BPS Guide to PHARMACOLOGY.
  33. 1 2 Meneses A (11 March 2014). The Role of 5-HT Systems on Memory and Dysfunctional Memory: Emergent Targets for Memory Formation and Memory Alterations. Elsevier Science. pp. 23–. ISBN   978-0-12-801083-9.
  34. ↑ Olivier B, van Wijngaarden I, Soudijn W (10 July 1997). Serotonin Receptors and their Ligands. Elsevier. pp. 118–. ISBN   978-0-08-054111-2.
  35. ↑ Creed-Carson M, Oraha A, Nobrega JN (June 2011). "Effects of 5-HT(2A) and 5-HT(2C) receptor antagonists on acute and chronic dyskinetic effects induced by haloperidol in rats". Behavioural Brain Research. 219 (2): 273–279. doi:10.1016/j.bbr.2011.01.025. PMID   21262266. S2CID   205882443.
  36. ↑ Coyne CP (9 January 2008). Comparative Diagnostic Pharmacology: Clinical and Research Applications in Living-System Models. John Wiley & Sons. pp. 104–. ISBN   978-0-470-34429-3.
  37. ↑ Muller CP, Jacobs B (30 December 2009). Handbook of the Behavioral Neurobiology of Serotonin. Academic Press. pp. 592–. ISBN   978-0-08-087817-1.
  38. ↑ Henry JP, Sagné C, Botton D, Isambert MF, Gasnier B (1998). Molecular Pharmacology of the Vesicular Monoamine Transporter. Advances in Pharmacology. Vol. 42. San Diego, Calif.: Academic Press. pp. 236–9 (237). doi:10.1016/s1054-3589(08)60736-x. ISBN   978-0-08-058134-7. PMID   9327887.
  39. ↑ Holze F, Madsen MK, Svarer C, Gillings N, Stenbaek DS, Rudin D, Duthaler U, Liechti ME, Fisher PM, Knudsen GM (August 2024). "Ketanserin exhibits dose- and concentration-proportional serotonin 2A receptor occupancy in healthy individuals: Relevance for psychedelic research". Eur Neuropsychopharmacol. 88: 43–48. doi:10.1016/j.euroneuro.2024.07.003.
  40. ↑ US 4335127,Vandenberk J, Kennis L, Van der Aa M, Van Heertum A,issued 1982, assigned to Janssen Pharmaceutica, N.V.
  41. ↑ EP 0098499,Signorini R, Verga A,issued 1984, assigned to Ravizza SpA
  42. ↑ CN 106866625,Shiwen R, et al.,issued 2017, assigned to Shanghai Ding Ya Pharmaceutical Chemistry Science And Technology Ltd)
  43. ↑ Fakhraian H, Heydary M (January 2014). "Reinvestigation of the Synthesis of Ketanserin (5) and its Hydrochloride Salt (5. HCl) via 3-(2-Chloroethyl)-2, 4-(1H, 3H)-quinazolinedione (2) or Dihydro-5H-oxazole (2, 3-b) quinazolin-5-one (1)". Journal of Heterocyclic Chemistry. 51 (1): 151–156. doi:10.1002/jhet.1897..
  44. ↑ Herndon JL, Ismaiel A, Ingher SP, Teitler M, Glennon RA (December 1992). "Ketanserin analogues: structure-affinity relationships for 5-HT2 and 5-HT1C serotonin receptor binding". Journal of Medicinal Chemistry. 35 (26): 4903–10. doi:10.1021/jm00104a017. PMID   1479590.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.