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

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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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