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 ayahuasca (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">Psychedelic drug</span> Hallucinogenic class of psychoactive drug

Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states and a perceived "expansion of consciousness". Also referred to as classic hallucinogens or serotonergic hallucinogens, the term psychedelic is sometimes used more broadly to include various types of hallucinogens, such as those which are atypical or adjacent to psychedelia like salvia and MDMA, respectively.

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

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin, is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad. It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, the power, bufo, and toad venom.

<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-MeO-AMT</span> Chemical compound

5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.

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">5-Methoxytryptamine</span> Chemical compound

5-Methoxytryptamine, also known as serotonin methyl ether or O-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to occur naturally in the body in low levels, especially in the pineal gland. It is formed via O-methylation of serotonin or N-deacetylation of melatonin.

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">Sarpogrelate</span> Chemical compound

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

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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">Serotonin releasing agent</span> Class of compounds

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<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">Volinanserin</span> Chemical compound

Volinanserin (INN) is a highly selective 5-HT2A receptor antagonist that is frequently used in scientific research to investigate the function of the 5-HT2A receptor. It was also tested in clinical trials as a potential antipsychotic, antidepressant, and treatment for insomnia but was never marketed.

<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.

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

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<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.

Hyperlocomotion, also known as locomotor hyperactivity, hyperactivity, or increased locomotor activity, is an effect of certain drugs in animals in which locomotor activity (locomotion) is increased. It is induced by certain drugs like psychostimulants and NMDA receptor antagonists and is reversed by certain other drugs like antipsychotics and certain antidepressants. Stimulation of locomotor activity is thought to be mediated by increased signaling in the nucleus accumbens.

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References

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  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.
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