Ketanserin

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Ketanserin
Ketanserin.png
Systematic (IUPAC) name
3-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}quinazoline-2,4(1H,3H)-dione
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 74050-98-9 YesY
ATC code C02KD01 (WHO) QD03AX90 (WHO)
PubChem CID: 3822
IUPHAR/BPS 88
ChemSpider 3690 YesY
UNII 97F9DE4CT4 YesY
KEGG D02363 YesY
ChEBI CHEBI:6123 N
ChEMBL CHEMBL51 YesY
Chemical data
Formula C22H22FN3O3
Molecular mass 395.43 g/mol
  • 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) YesY
  • Key:FPCCSQOGAWCVBH-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Ketanserin (INN, USAN, BAN) (brand name Sufrexal; former code name R41468) is a drug used clinically as an antihypertensive agent and in scientific research to study the serotonin system; specifically, the 5-HT2A receptor.[1] It was discovered at Janssen Pharmaceutica in 1980.

Uses

Antihypertensive

It is classified as an antihypertensive by the World Health Organization[2] and the National Institute of Health.[3]

It has been used to reverse pulmonary hypertension caused by protamine (which in turn was administered to reverse the effects of heparin overdose).[4]

The reduction in hypertension is not associated with reflex tachycardia.[5]

It has been used in cardiac surgery.[6]

As a radioligand

With tritium (3H) radioactively labeled ketanserin is used as a radioligand for the serotonin 5-HT2A receptor, e.g. in receptor binding assays and autoradiography.[7] This radiolabeling enables the study of the serotonin-2A receptor distribution in the human brain.[8]

An autoradiography study of the human cerebellum has found an increasing binding of H-3-ketanserin with age (from below 50 femtomol per milligram tissue at around 30 years og age to over 100 above 75 years).[9] The same research team found no significant correlation with age in their homogenate binding study.

As a blocker with another radioligand

Ketanserin has also been used with carbon (11C) radioactively labeled NNC112 in order to image cortical D1 receptors without contamination by 5-HT2A receptors.[10]

Pharmacology

Ketanserin is a high-affinity antagonist of the 5-HT2A receptor (Ki = 2-3 nM).[11][12] However, it also blocks the H1 receptor with high affinity (Ki = 2 nM).[12][13] In addition, ketanserin less potently antagonizes the α1-adrenergic (Ki = ~40 nM),[13] α2-adrenergic = ~200 nM), 5-HT1D (Ki = ? nM),[11][14] 5-HT2B (Ki = ? nM),[15] 5-HT2C (Ki = 100 nM),[13] 5-HT6 (Ki = ~300 nM),[16] 5-HT7 (Ki = ? nM),[11] D1 (~300 nM),[13] and D2 (Ki = ~500 nM) receptors.[12][13] It also blocks the vesicular monoamine transporter (VMAT2).[17][18]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ ATC/DDD Index
  3. ↑ Ketanserin
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 11.2 Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ 12.0 12.1 12.2 NIMH Psychoactive Drug Screening Program
  13. ↑ 13.0 13.1 13.2 13.3 13.4 Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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