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 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12569067	Antagonist 2778		2.7 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Skin ulcer 8 Sources: http://www.medicatione.com/?c=drug&s=sufrexal%20p&ingredient=benzocaine/ketanserin	Curative	Approved 8429	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 8429	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 8429	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 40 Sources: http://www.medicatione.com/?c=drug&s=sufrexal%20p&ingredient=benzocaine/ketanserin	Curative	Approved 8429	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 8429	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
High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action.	1999 May	10217294
The role of serotonin(2) receptors in mediating cocaine-induced convulsions.	2000 Apr	10764922
Expression of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors in the mouse embryo.	2000 Nov	10978843
Gastroprokinetic effect and mechanism of SK-896, a new motilin analogue, during the interdigestive period in conscious dogs.	2001	11490202
Ketanserin for the treatment of preeclampsia.	2001	11234612
Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling.	2001 Apr	11259531
Role of prostanoids and endothelins in the prevention of cyclosporine-induced nephrotoxicity.	2001 Apr-May	11418017
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
5-HT1A receptor-mediated activation of G-protein-gated inwardly rectifying K+ current in rat periaqueductal gray neurons.	2001 Aug	11489454
Ex vivo binding of flibanserin to serotonin 5-HT1A and 5-HT2A receptors.	2001 Feb	11243720
Pharmacological characterisation of the decrease in 5-HT synthesis in the mouse brain evoked by the selective serotonin re-uptake inhibitor citalopram.	2001 Feb	11218075
The distribution of a kinin-like peptide and its co-localization with a CRF-like peptide in the blood-feeding bug, Rhodnius prolixus.	2001 Feb	11179809
Serotonin modifies the neuronal inhibitory responses to gamma-aminobutyric acid in the red nucleus: a microiontophoretic study in the rat.	2001 Jan	11161597
Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa.	2001 Jul	11431241
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
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.	2001 Jun	11414657
The inhibitory effect of serotonin on the spontaneous discharge of suprachiasmatic neurons in hypothalamic slice is mediated by 5-HT(7) receptor.	2001 Mar 1	11306191
Systemic vascular effects of thrombin and thrombin receptor activating peptide in rats.	2001 Mar 15	11323004
Serotonin-induced hypercontraction through 5-hydroxytryptamine 1B receptors in atherosclerotic rabbit coronary arteries.	2001 Mar 6	11238275
Do mucosal mast cells contribute to the immediate asthma response?	2001 May	11430471
Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism.	2001 May 18	11412837
Antidepressant-like effects of aniracetam in aged rats and its mode of action.	2001 Nov	11702095
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
Serotonin receptors modulate GABA(A) receptor channels through activation of anchored protein kinase C in prefrontal cortical neurons.	2001 Sep 1	11517239
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 `Sat Dec 16 17:56:06 GMT 2023` Edited by `admin` on `Sat Dec 16 17:56:06 GMT 2023`
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