U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H22FN3O3
Molecular Weight 395.4276
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETANSERIN

SMILES

c1ccc2c(c1)c(=O)n(CCN3CCC(CC3)C(=O)c4ccc(cc4)F)c(n2)O

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
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

Sources: Hideya Sait, Masaru Minami (1992) 'Antihypertensive Drugs Today', p.194

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.70000000000000018 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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
Curative
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
Curative
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
Curative
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

PubMed

TitleDatePubMed
Gastroprokinetic effect and mechanism of SK-896, a new motilin analogue, during the interdigestive period in conscious dogs.
2001
Effect of fluvoxamine and N-methyl-D-aspartate receptor antagonists on shock-induced depression in mice.
2001 Apr
Use of topical ketanserin for the treatment of ulcers in leprosy patients.
2001 Apr-Jun
Blood pressure patterns in pregnant patients on oral ketanserin.
2001 Apr-May
Role of prostanoids and endothelins in the prevention of cyclosporine-induced nephrotoxicity.
2001 Apr-May
Disturbance of serotonin 5HT2 receptors in remitted patients suffering from hereditary depressive disorder.
2001 Aug
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
Complex interaction of ergovaline with 5-HT2A, 5-HT1B/1D, and alpha1 receptors in isolated arteries of rat and guinea pig.
2001 Aug
Evidence that hypophagia induced by d-fenfluramine and d-norfenfluramine in the rat is mediated by 5-HT2C receptors.
2001 Aug
5-HT1A receptor-mediated activation of G-protein-gated inwardly rectifying K+ current in rat periaqueductal gray neurons.
2001 Aug
Blockade of D1 dopamine receptors in the ventral tegmental area decreases cocaine reward: possible role for dendritically released dopamine.
2001 Aug 1
Catecholamines inhibit lipid peroxidation in young, aged, and Alzheimer's disease brain.
2001 Aug 1
Activation of spinal serotonin(2A/2C) receptors augments nociceptive responses in the rat.
2001 Aug 10
Serotonin 2A receptor regulation of striatal neuropeptide gene expression is selective for tachykinin, but not enkephalin neurons following dopamine depletion.
2001 Aug 15
Role of 5-HT(2) receptor subtypes in depletion of 5-HT induced by p-chloroamphetamine in the mouse frontal cortex.
2001 Aug 24
Serotonin(2) receptors mediate respiratory recovery after cervical spinal cord hemisection in adult rats.
2001 Dec
Influence of serotonin on the glutamate-induced excitations of secondary vestibular neurons in the rat.
2001 Dec
Inhibitory presynaptic 5-hydroxytryptamine(2A) receptors regulate evoked glutamate release from rat cerebellar mossy fibers.
2001 Dec
Researching the antidepressant actions of Hypericum perforatum (St. John's wort) in animals and man.
2001 Jul
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
Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa.
2001 Jul
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
Chronic intermittent hypoxia elicits serotonin-dependent plasticity in the central neural control of breathing.
2001 Jul 15
Modulation of 5-HT(2A) receptor-mediated head-twitch behaviour in the rat by 5-HT(2C) receptor agonists.
2001 Jul-Aug
The effects of hypothyroidism on 5-HT1A and 5-HT2A receptors and the serotonin transporter protein in the rat brain.
2001 Jul-Aug
Platelet 3H ketanserin binding in migraine.
2001 Jun
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.
2001 Jun
Different receptor subtypes are involved in the serotonin-induced modulation of epileptiform activity in rat frontal cortex in vitro.
2001 Jun
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.
2001 Jun
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.
2001 Jun
Pharmacological evaluation of (+)-2- [123I]A-69024: a radioligand for in vivo studies of dopamine D1 receptors.
2001 Jun 29
Relaxation induced by serotonin and sumatriptan in isolated guinea pig gallbladder strips.
2001 Mar
Do mucosal mast cells contribute to the immediate asthma response?
2001 May
Characterisation of agonist binding on human 5-HT2C receptor isoforms.
2001 May 11
Antidepressant-like effects of aniracetam in aged rats and its mode of action.
2001 Nov
Platelet inhibition reduces cyclic flow variations and neointimal proliferation in normal and hypercholesterolemic-atherosclerotic canine coronary arteries.
2001 Nov 6
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
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
Physiology and pathophysiology of the serotonergic system and its implications on mental and physical performance. Part II.
2001 Oct
Activation of Erk mitogen-activated protein kinase proteins by vascular serotonin receptors.
2001 Oct
Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists.
2001 Oct
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.
2001 Oct
Neuroepithelial bodies in mammalian lung express functional serotonin type 3 receptor.
2001 Oct
Ketanserin attenuates the behavioural effects of corticosterone: implications for 5-HT(2A) receptor regulation.
2001 Oct 5
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
On the role of serotonin2A/2C receptors in the sensitization to cocaine.
2001 Sep
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
Serotonin receptors modulate GABA(A) receptor channels through activation of anchored protein kinase C in prefrontal cortical neurons.
2001 Sep 1
Stimulation of 5-HT2 receptors in the nucleus tractus solitarius enhances NMDA receptor-mediated reflex-evoked bradycardiac responses in the rat.
2001 Sep 17
Effects of 5-HT(2) receptor antagonists on the anti-immobility effects of imipramine in the forced swimming test with mice.
2001 Sep 21
Patents

Sample Use Guides

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
2% and 20% topical ketanserin significantly accelerates both the vascular epithelial rates of wound healing in full-thickness nonpathologic skin wounds.
Name Type Language
KETANSERIN
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
KETANSERIN [USAN]
Common Name English
KETANSERIN [INN]
Common Name English
R-41,468
Code English
KETANSERIN [WHO-DD]
Common Name 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 [MI]
Common Name English
R-41468
Code English
Classification Tree Code System Code
WHO-VATC QD03AX90
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
WHO-ATC C02KD01
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
NCI_THESAURUS C66885
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
WHO-VATC QC02KD01
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
Code System Code Type Description
IUPHAR
88
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
277-680-2
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
DRUG CENTRAL
1524
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
NCI_THESAURUS
C604
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
DRUG BANK
DB12465
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL51
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
INN
5087
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
MESH
D007650
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
WIKIPEDIA
KETANSERIN
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
FDA UNII
97F9DE4CT4
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
MERCK INDEX
M6614
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY Merck Index
EPA CompTox
74050-98-9
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
EVMPD
SUB08366MIG
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
CAS
74050-98-9
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
PUBCHEM
3822
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY
RXCUI
6131
Created by admin on Sat Jun 26 13:20:59 UTC 2021 , Edited by admin on Sat Jun 26 13:20:59 UTC 2021
PRIMARY RxNorm