KETANSERIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H22FN3O3
Molecular Weight	395.4268
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(C=C1)C(=O)C2CCN(CCN3C(=O)NC4=C(C=CC=C4)C3=O)CC2

InChI

InChIKey=FPCCSQOGAWCVBH-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C22H22FN3O3
Molecular Weight	395.4268
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17147663

Ketanserin is a selective 5HT2A receptor antagonist which was initially developed as an anti-hypertensive medicine. However, now the drug is available as a topical gel formulation for the treatment of wounds, burns, ulcers and anal fissure (Sufrexal brand name). The drug action is explained by its ability to accelerate epithelialization.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2a (5-HT2a) receptor 229 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12569067	Antagonist 2737		2.7 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Skin ulcer 7 Sources: http://www.medicatione.com/?c=drug&s=sufrexal%20p&ingredient=benzocaine/ketanserin	Curative	Approved 8307	Sufrexal Approved Use Non-neoplastic dermal and uterine cervix ulcers. Traumatic wounds such as decubitus ulcers. Preparation of tissue for grafting and flaps. Uninfected burns. Regeneration of the uterine cervix. Anal fissure
Cervix ulcer 2 Sources: http://www.medicatione.com/?c=drug&s=sufrexal%20p&ingredient=benzocaine/ketanserin	Curative	Approved 8307	Sufrexal Approved Use Non-neoplastic dermal and uterine cervix ulcers. Traumatic wounds such as decubitus ulcers. Preparation of tissue for grafting and flaps. Uninfected burns. Regeneration of the uterine cervix. Anal fissure
Traumatic wounds 2 Sources: http://www.medicatione.com/?c=drug&s=sufrexal%20p&ingredient=benzocaine/ketanserin	Curative	Approved 8307	Sufrexal Approved Use Non-neoplastic dermal and uterine cervix ulcers. Traumatic wounds such as decubitus ulcers. Preparation of tissue for grafting and flaps. Uninfected burns. Regeneration of the uterine cervix. Anal fissure
Burn 39 Sources: http://www.medicatione.com/?c=drug&s=sufrexal%20p&ingredient=benzocaine/ketanserin	Curative	Approved 8307	Sufrexal Approved Use Non-neoplastic dermal and uterine cervix ulcers. Traumatic wounds such as decubitus ulcers. Preparation of tissue for grafting and flaps. Uninfected burns. Regeneration of the uterine cervix. Anal fissure
Anal fissure 6 Sources: http://www.medicatione.com/?c=drug&s=sufrexal%20p&ingredient=benzocaine/ketanserin	Curative	Approved 8307	Sufrexal Approved Use Non-neoplastic dermal and uterine cervix ulcers. Traumatic wounds such as decubitus ulcers. Preparation of tissue for grafting and flaps. Uninfected burns. Regeneration of the uterine cervix. Anal fissure

PubMed

Title	Date	PubMed
Gastroprokinetic effect and mechanism of SK-896, a new motilin analogue, during the interdigestive period in conscious dogs.	2001	11490202
Effect of fluvoxamine and N-methyl-D-aspartate receptor antagonists on shock-induced depression in mice.	2001 Apr	11480226
Use of topical ketanserin for the treatment of ulcers in leprosy patients.	2001 Apr-Jun	11579646
Blood pressure patterns in pregnant patients on oral ketanserin.	2001 Apr-May	11447496
Role of prostanoids and endothelins in the prevention of cyclosporine-induced nephrotoxicity.	2001 Apr-May	11418017
Disturbance of serotonin 5HT2 receptors in remitted patients suffering from hereditary depressive disorder.	2001 Aug	11556203
In vivo evaluation of 4-[123I]iodo-N-[2[4-(6-trifluoromethyl-2-pyridinyl)-1-piperazinyl]ethyl]benzamide, a potential SPECT radioligand for the 5-HT1A receptor.	2001 Aug	11518645
Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig.	2001 Aug	11518230
Evidence that hypophagia induced by d-fenfluramine and d-norfenfluramine in the rat is mediated by 5-HT2C receptors.	2001 Aug	11489456
5-HT1A receptor-mediated activation of G-protein-gated inwardly rectifying K+ current in rat periaqueductal gray neurons.	2001 Aug	11489454
Blockade of D1 dopamine receptors in the ventral tegmental area decreases cocaine reward: possible role for dendritically released dopamine.	2001 Aug 1	11466456
Catecholamines inhibit lipid peroxidation in young, aged, and Alzheimer's disease brain.	2001 Aug 1	11461768
Activation of spinal serotonin(2A/2C) receptors augments nociceptive responses in the rat.	2001 Aug 10	11489268
Serotonin 2A receptor regulation of striatal neuropeptide gene expression is selective for tachykinin, but not enkephalin neurons following dopamine depletion.	2001 Aug 15	11483243
Role of 5-HT(2) receptor subtypes in depletion of 5-HT induced by p-chloroamphetamine in the mouse frontal cortex.	2001 Aug 24	11511381
Serotonin(2) receptors mediate respiratory recovery after cervical spinal cord hemisection in adult rats.	2001 Dec	11717232
Influence of serotonin on the glutamate-induced excitations of secondary vestibular neurons in the rat.	2001 Dec	11716569
Inhibitory presynaptic 5-hydroxytryptamine(2A) receptors regulate evoked glutamate release from rat cerebellar mossy fibers.	2001 Dec	11714900
Researching the antidepressant actions of Hypericum perforatum (St. John's wort) in animals and man.	2001 Jul	11518072
Synthesis and 5-HT2A antagonist activity of derivatives of the novel heterocycles indolo[3,2-d]pyrrolo[3,2-g]azecine and benzo[d]pyrrolo[3,2-g]azecine compared to the benz[d]indolo[2,3-g]azecine derivative LE 300.	2001 Jul	11512275
Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa.	2001 Jul	11431241
Effects of 5-HT2 and 5-HT3 receptors on the modulation of nociceptive transmission in rat spinal cord according to the formalin test.	2001 Jul 13	11470259
Chronic intermittent hypoxia elicits serotonin-dependent plasticity in the central neural control of breathing.	2001 Jul 15	11438615
Modulation of 5-HT(2A) receptor-mediated head-twitch behaviour in the rat by 5-HT(2C) receptor agonists.	2001 Jul-Aug	11509227
The effects of hypothyroidism on 5-HT1A and 5-HT2A receptors and the serotonin transporter protein in the rat brain.	2001 Jul-Aug	11508497
Platelet 3H ketanserin binding in migraine.	2001 Jun	11472383
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.	2001 Jun	11459121
Different receptor subtypes are involved in the serotonin-induced modulation of epileptiform activity in rat frontal cortex in vitro.	2001 Jun	11453105
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.	2001 Jun	11414657
Pharmacological evaluation of (+)-2- [123I]A-69024: a radioligand for in vivo studies of dopamine D1 receptors.	2001 Jun 29	11476188
Relaxation induced by serotonin and sumatriptan in isolated guinea pig gallbladder strips.	2001 Mar	11426669
Do mucosal mast cells contribute to the immediate asthma response?	2001 May	11430471
Characterisation of agonist binding on human 5-HT2C receptor isoforms.	2001 May 11	11426831
Antidepressant-like effects of aniracetam in aged rats and its mode of action.	2001 Nov	11702095
Expression of serotonin 5-HT(2A) receptors in the human cerebellum and alterations in schizophrenia.	2001 Nov	11574947
Platelet inhibition reduces cyclic flow variations and neointimal proliferation in normal and hypercholesterolemic-atherosclerotic canine coronary arteries.	2001 Nov 6	11696474
Binding affinity of a newly synthesized 5-HT2 antagonist, AT-1015 (N-[2-[4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-piperidino]ethyl]-1-formyl-4-piperidinecarboxamide monohydrochloride monohydrate), in the rabbit platelet membrane.	2001 Oct	11642330
Enhanced contraction to 5-hydroxytryptamine is not due to "unmasking" of 5-hydroxytryptamine(1b) receptors in the mesenteric artery of the deoxycorticosterone acetate-salt rat.	2001 Oct	11641304
Physiology and pathophysiology of the serotonergic system and its implications on mental and physical performance. Part II.	2001 Oct	11590475
Activation of Erk mitogen-activated protein kinase proteins by vascular serotonin receptors.	2001 Oct	11588524
Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists.	2001 Oct	11562430
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.	2001 Oct	11561066
Neuroepithelial bodies in mammalian lung express functional serotonin type 3 receptor.	2001 Oct	11557597
Ketanserin attenuates the behavioural effects of corticosterone: implications for 5-HT(2A) receptor regulation.	2001 Oct 5	11675041
Autoradiographic mapping of 5-HT(1B) and 5-HT(1D) receptors in the post mortem human brain using [(3)H]GR 125743.	2001 Oct 5	11578619
On the role of serotonin2A/2C receptors in the sensitization to cocaine.	2001 Sep	11596864
Prostaglandins may participate in opioidergic and cholinergic control of the diurnal changes of tuberoinfundibular dopaminergic neuronal activity and serum prolactin level in ovariectomized, estrogen-treated rats.	2001 Sep 1	11604250
Serotonin receptors modulate GABA(A) receptor channels through activation of anchored protein kinase C in prefrontal cortical neurons.	2001 Sep 1	11517239
Stimulation of 5-HT2 receptors in the nucleus tractus solitarius enhances NMDA receptor-mediated reflex-evoked bradycardiac responses in the rat.	2001 Sep 17	11570703
Effects of 5-HT(2) receptor antagonists on the anti-immobility effects of imipramine in the forced swimming test with mice.	2001 Sep 21	11567652

Patents

Sample Use Guides

In Vivo Use Guide

Apply a thin layer twice a day (topical gel) or use one applicator every 24 hours at night before bed for two weeks (vaginal application). In case of anal fissure, apply a small amount of the gel digitally in the anus area 3 times a day, preferably after bowel movement and cleaning the area with soap and water. The minimum recommended treatment time is 15 days.

Route of Administration: Topical

In Vitro Use Guide

2% and 20% topical ketanserin significantly accelerates both the vascular epithelial rates of wound healing in full-thickness nonpathologic skin wounds.

Substance Class	Chemical Created by `admin` on `Sun Dec 18 21:05:57 UTC 2022` Edited by `admin` on `Sun Dec 18 21:05:57 UTC 2022`
Record UNII	97F9DE4CT4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KETANSERIN

Official Name

English

KETANSERIN [USAN]

Common Name

English

ketanserin [INN]

Common Name

English

R-41,468

Code

English

3-(2-(4-(P-FLUOROBENZOYL)PIPERIDINO)ETHYL)-2,4-(1H,3H)-QUINAZOLINEDIONE

Common Name

English

KETANSERIN [MART.]

Common Name

English

2,4(1H,3H)-QUINAZOLINEDIONE, 3-(2-(4-(4-FLUOROBENZOYL)-1-PIPERIDINYL)ETHYL)-

Systematic Name

English

Ketanserin [WHO-DD]

Common Name

English

KETANSERIN [MI]

Common Name

English

R-41468

Code

English

Classification Tree Code System Code

WHO-VATC

QD03AX90