Ketanserin | CAS#74050-98-9 | 5-HT2A receptor antagonist | hypertension

Ketanserin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540257

CAS#: 74050-98-9 (free base)

Description: Ketanserin is a 5-HT2A receptor antagonist and potential α1-adrenergic receptor antagonist used to treat hypertension. It decreases blood pressure, improves left ventricular remodeling, increases capillary density in myocardial tissue, and may suppress TRPV1 channel-evoked thermal hyperalgesia.

Chemical Structure

Ketanserin

CAS# 74050-98-9 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540257
Name: Ketanserin
CAS#: 74050-98-9 (free base)
Chemical Formula: C22H22FN3O3
Exact Mass: 395.16
Molecular Weight: 395.430
Elemental Analysis: C, 66.82; H, 5.61; F, 4.80; N, 10.63; O, 12.14

Price and Availability

Size	Price	Availability
100mg	USD 150	Ready to ship
200mg	USD 250	Ready to ship
500mg	USD 450	Ready to ship
1g	USD 750	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 83846-83-7 (tartrate) 74050-98-9 (free base)

Synonym: Ketanserin; R 41468; R-41468; R41468;

IUPAC/Chemical Name: 3-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)quinazoline-2,4(1H,3H)-dione

InChi Key: FPCCSQOGAWCVBH-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(N1CCN2CCC(C(C3=CC=C(F)C=C3)=O)CC2)NC4=C(C=CC=C4)C1=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#C21B10B20

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Ketanserin is a selective 5-HT2 receptor antagonist that also blocks hERG current (IhERG) in a concentration-dependent manner (IC50=0.11 μM).
In vitro activity:	Cells were treated with 5-HT (1 µM 5-HT hydrochloride was added to the cell culture medium) or with both 5-HT and ketanserin (5-HT+K; 0.1 μM ketanserin was added 30 minutes before the addition of 5-HT) for 72 hours. In addition to the enhanced expression of α-SMA mRNA in PFs (portal fibroblast), the phosphorylation of smad2/3 and the expression of collagen I, collagen III, and α-SMA protein increased after 72 hours of culture. Ketanserin significantly decreased the phosphorylation of smad2 and smad3 by 52% and 58%, respectively, and reduced the expression of collagen I and collagen III protein by 63% and 56%, respectively; this was concurrent with 63% and 76% decreases in α-SMA mRNA and protein expression. The transdifferentiation of PFs into MFs was also suppressed because α-SMA–positive cells were notably reduced 72 hours after ketanserin administration. The results indicated that ketanserin inhibited 5-HT–activated TGF-β1–smad2/3 signaling in vitro and thereby depressed the MF conversion of PFs. Reference: Liver Transpl. 2014 Nov;20(11):1317-26. https://pubmed.ncbi.nlm.nih.gov/25045122/
In vivo activity:	To investigate whether ketanserin reduces susceptibility to colitis, colitis was induced in mice using DSS. The mice with DSS-induced colitis exhibited a continuous decrease in body weight from day 4 to day 7 and shortened colon lengths. By contrast, the administration of ketanserin during the induction of colitis significantly prevented the decrease in body weight and colon shortening. A histological examination of the colons of the mice with DSS-induced colitis revealed severe inflammation with ulcerative lesions, loss of crypts and the infiltration of inflammatory cells, whereas treatment with ketanserin alleviated these histological changes and damage to the colon, characterized by a decrease in the loss of architecture, fewer ulcerative lesions, and a decrease in inflammatory cell infiltration into the inflamed mucosa. The data therefore suggest that ketanserin exerts a potent therapeutic effect, ameliorating DSS-induced colitis. Reference: Int J Mol Med. 2016 Mar;37(3):659-68. https://pubmed.ncbi.nlm.nih.gov/26865503/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	16.7	42.16

Preparing Stock Solutions

The following data is based on the product molecular weight 395.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Bergqvist D, Arvidsson S, Haglund U, Hedner U, Lindblad B. The influence of ketanserin on hemostasis in vitro. Thromb Res. 1986 Jul 15;43(2):237-41. doi: 10.1016/0049-3848(86)90065-4. PMID: 2943051. 2. Chen L, Chen G, Guo Y, Liu L, Xiao L, Fan W, Shi B, Qian Y. Ketanserin, a serotonin 2A receptor antagonist, alleviates ischemia-related biliary fibrosis following donation after cardiac death liver transplantation in rats. Liver Transpl. 2014 Nov;20(11):1317-26. doi: 10.1002/lt.23947. PMID: 25045122. 3. Xiao J, Shao L, Shen J, Jiang W, Feng Y, Zheng P, Liu F. Effects of ketanserin on experimental colitis in mice and macrophage function. Int J Mol Med. 2016 Mar;37(3):659-68. doi: 10.3892/ijmm.2016.2486. Epub 2016 Feb 10. PMID: 26865503; PMCID: PMC4771115. 4. Liu C, Zhang X, Zhou JX, Wei W, Liu DH, Ke P, Zhang GF, Cai GJ, Su DF. The protective action of ketanserin against lipopolysaccharide-induced shock in mice is mediated by inhibiting inducible NO synthase expression via the MEK/ERK pathway. Free Radic Biol Med. 2013 Dec;65:658-666. doi: 10.1016/j.freeradbiomed.2013.07.045. Epub 2013 Aug 13. PMID: 23954471.
In vitro protocol:	1. Bergqvist D, Arvidsson S, Haglund U, Hedner U, Lindblad B. The influence of ketanserin on hemostasis in vitro. Thromb Res. 1986 Jul 15;43(2):237-41. doi: 10.1016/0049-3848(86)90065-4. PMID: 2943051. 2. Chen L, Chen G, Guo Y, Liu L, Xiao L, Fan W, Shi B, Qian Y. Ketanserin, a serotonin 2A receptor antagonist, alleviates ischemia-related biliary fibrosis following donation after cardiac death liver transplantation in rats. Liver Transpl. 2014 Nov;20(11):1317-26. doi: 10.1002/lt.23947. PMID: 25045122.
In vivo protocol:	1. Xiao J, Shao L, Shen J, Jiang W, Feng Y, Zheng P, Liu F. Effects of ketanserin on experimental colitis in mice and macrophage function. Int J Mol Med. 2016 Mar;37(3):659-68. doi: 10.3892/ijmm.2016.2486. Epub 2016 Feb 10. PMID: 26865503; PMCID: PMC4771115. 2. Liu C, Zhang X, Zhou JX, Wei W, Liu DH, Ke P, Zhang GF, Cai GJ, Su DF. The protective action of ketanserin against lipopolysaccharide-induced shock in mice is mediated by inhibiting inducible NO synthase expression via the MEK/ERK pathway. Free Radic Biol Med. 2013 Dec;65:658-666. doi: 10.1016/j.freeradbiomed.2013.07.045. Epub 2013 Aug 13. PMID: 23954471.

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1: Singh S, Dinesh N, Kaur PK, Shamiulla B. Ketanserin, an antidepressant, exerts its antileishmanial action via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR) enzyme of Leishmania donovani. Parasitol Res. 2014 Jun;113(6):2161-8. doi: 10.1007/s00436-014-3868-y. Epub 2014 Apr 12. PubMed PMID: 24728519.

2: Bijvank SW, Visser W, Duvekot JJ, Steegers EA, Edens MA, Roofthooft DW, Vulto AG, Hanff LM. Ketanserin versus dihydralazine for the treatment of severe hypertension in early-onset preeclampsia: a double blind randomized controlled trial. Eur J Obstet Gynecol Reprod Biol. 2015 Jun;189:106-11. doi: 10.1016/j.ejogrb.2015.02.002. Epub 2015 Mar 10. PubMed PMID: 25892082.

3: Chen L, Chen G, Guo Y, Liu L, Xiao L, Fan W, Shi B, Qian Y. Ketanserin, a serotonin 2A receptor antagonist, alleviates ischemia-related biliary fibrosis following donation after cardiac death liver transplantation in rats. Liver Transpl. 2014 Nov;20(11):1317-26. doi: 10.1002/lt.23947. PubMed PMID: 25045122.

4: Wang D, Zhou X, Hong Y. Effects of a combination of ketanserin and propranolol on inflammatory hyperalgesia in rats. Eur J Pharmacol. 2013 Dec 5;721(1-3):126-32. doi: 10.1016/j.ejphar.2013.09.043. Epub 2013 Sep 25. PubMed PMID: 24076184.

5: Miryala CS, Hiegel C, Uphouse L. Comparison of female Fischer and Sprague-Dawley rats in the response to ketanserin. Pharmacol Biochem Behav. 2013 Dec;114-115:52-7. doi: 10.1016/j.pbb.2013.10.024. Epub 2013 Nov 4. PubMed PMID: 24201045; PubMed Central PMCID: PMC3902122.

6: Aljuffali IA, Brainard BM, Moore JN, Kwon S, Allen D, Robertson TP, Arnold RD. Pharmacokinetic assessment of ketanserin in the horse. J Vet Pharmacol Ther. 2012 Oct;35(5):472-7. doi: 10.1111/j.1365-2885.2011.01346.x. Epub 2011 Nov 18. PubMed PMID: 22091605.

7: Schaafstra L, van Roon EN, Morssink LP, de Vries NK. The effect of maternal ketanserin use on the circulation of the neonate: a prospective, observational study. Eur J Obstet Gynecol Reprod Biol. 2012 May;162(1):11-5. doi: 10.1016/j.ejogrb.2012.01.013. Epub 2012 Feb 19. PubMed PMID: 22349270.

8: Liu C, Zhang GF, Song SW, Cai GJ, Liu WH, Miao CY, Su DF. Effects of ketanserin on endotoxic shock and baroreflex function in rodents. J Infect Dis. 2011 Nov 15;204(10):1605-12. doi: 10.1093/infdis/jir609. Epub 2011 Sep 14. PubMed PMID: 21917879.

9: Peiró AM, Climent L, Zapater P, Horga A, Horga JF. Ketanserin potentiates morphine-induced antinociception mediated by kappa-receptor activation. Pharmacol Res. 2011 Jul;64(1):80-4. doi: 10.1016/j.phrs.2011.02.009. Epub 2011 Mar 21. PubMed PMID: 21420495.

10: Van Peer A, Woestenborghs R, Embrechts L, Heykants J. Pharmacokinetic approach to equilibrium between ketanserin and ketanserin-ol. Eur J Clin Pharmacol. 1986;31(3):339-42. PubMed PMID: 3792431.

11: Bhatia KS, Szabo ST, Fowler JC, Wetsel WC, Lee TH. Reversal of long-term methamphetamine sensitization by combination of pergolide with ondansetron or ketanserin, but not mirtazapine. Behav Brain Res. 2011 Sep 30;223(1):227-32. doi: 10.1016/j.bbr.2011.04.045. Epub 2011 May 7. PubMed PMID: 21571009; PubMed Central PMCID: PMC3113440.

12: Coha B, Samardžić P, Dundjer I, Knežević-Praveček M. Cardiac arrhythmia as a side effect of ketanserin therapy in a patient with systemic scleroderma. Acta Dermatovenerol Croat. 2012;20(1):54-6. PubMed PMID: 22507478.

13: Leary WP, Reyes AJ, van der Byl K, Maharaj B. Comparative antihypertensive effects of ketanserin and a ketanserin-hydrochlorothiazide combination administered once daily. J Cardiovasc Pharmacol. 1987;10 Suppl 3:S127-34. PubMed PMID: 2446061.

14: Wang D, Gao Y, Ji H, Hong Y. Topical and systemic administrations of ketanserin attenuate hypersensitivity and expression of CGRP in rats with spinal nerve ligation. Eur J Pharmacol. 2010 Feb 10;627(1-3):124-30. doi: 10.1016/j.ejphar.2009.11.011. Epub 2009 Nov 11. PubMed PMID: 19913012.

15: Muguruza C, Moreno JL, Umali A, Callado LF, Meana JJ, González-Maeso J. Dysregulated 5-HT(2A) receptor binding in postmortem frontal cortex of schizophrenic subjects. Eur Neuropsychopharmacol. 2013 Aug;23(8):852-64. doi: 10.1016/j.euroneuro.2012.10.006. Epub 2012 Nov 21. PubMed PMID: 23176747; PubMed Central PMCID: PMC3586752.

16: Breckenridge A. Ageing, serotonin and ketanserin. Drugs. 1988;36 Suppl 1:44-54. Review. PubMed PMID: 3071462.

17: Bolte AC, van Eyck J, Gaffar SF, van Geijn HP, Dekker GA. Ketanserin for the treatment of preeclampsia. J Perinat Med. 2001;29(1):14-22. PubMed PMID: 11234612.

18: Beretta-Piccoli C, Amstein R, Bertel O, Brunner HR, Bühler FR, Follath F, Solèr M, Vallotton M. Antihypertensive efficacy of ketanserin alone or in combination with a beta-blocker or a diuretic: the Swiss Ketanserin Study. J Cardiovasc Pharmacol. 1987;10 Suppl 3:S119-23. PubMed PMID: 2446058.

19: Symoens J. Ketanserin: a novel cardiovascular drug. Blood Coagul Fibrinolysis. 1990 Jun;1(2):219-24. Review. PubMed PMID: 2130934.

20: Cazzola M, Guidetti E, Sepe J, Assogna G, Lucchetti G, Santangelo G, D'Amato G. Acute respiratory and cardiovascular effects of inhaled ketanserin in chronic obstructive pulmonary disease. A comparative study with intravenously administered ketanserin. Chest. 1990 Apr;97(4):901-5. PubMed PMID: 2182300.

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