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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 of KETANSERIN

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

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
2.7 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
The role of serotonin(2) receptors in mediating cocaine-induced convulsions.
2000 Apr
Mechanism of airway hyperresponsiveness to adenosine induced by allergen challenge in actively sensitized Brown Norway rats.
2001 Apr
Roles of 5-HT receptors in the release and action of secretin on pancreatic secretion in rats.
2001 Apr
Blood pressure patterns in pregnant patients on oral ketanserin.
2001 Apr-May
Monocyte 5-HT1A receptors mediate pindobind suppression of natural killer cell activity: modulation by catalase.
2001 Feb
Pharmacological characterisation of the decrease in 5-HT synthesis in the mouse brain evoked by the selective serotonin re-uptake inhibitor citalopram.
2001 Feb
Intestinal serotonin acts as a paracrine substance to mediate vagal signal transmission evoked by luminal factors in the rat.
2001 Feb 1
Activation of nicotinic receptors on GABAergic amacrine cells in the rabbit retina indirectly stimulates dopamine release.
2001 Jan-Feb
Analyses of [(18)F]altanserin bolus injection PET data. II: consideration of radiolabeled metabolites in humans.
2001 Jul
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.
2001 Jun
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.
2001 Jun
Could the 5-HT1B receptor inverse agonism affect learning consolidation?
2001 Mar
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
Systemic vascular effects of thrombin and thrombin receptor activating peptide in rats.
2001 Mar 15
Association study of the 5-HT(2A) receptor gene polymorphism, T102C and essential hypertension.
2001 May
Electrophysiological effects of cocaethylene, cocaine, and ethanol on dopaminergic neurons of the ventral tegmental area.
2001 May
Phrenic long-term facilitation requires 5-HT receptor activation during but not following episodic hypoxia.
2001 May
Antidepressant-like effects of aniracetam in aged rats and its mode of action.
2001 Nov
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
Ketanserin attenuates the behavioural effects of corticosterone: implications for 5-HT(2A) receptor regulation.
2001 Oct 5
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 23:15:23 UTC 2023
Edited
by admin
on Thu Jul 06 23:15:23 UTC 2023
Record UNII
97F9DE4CT4
Record Status Validated (UNII)
Record Version
  • Download
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
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
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
WHO-ATC C02KD01
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
NCI_THESAURUS C66885
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
WHO-VATC QC02KD01
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
Code System Code Type Description
IUPHAR
88
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
277-680-2
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
DRUG CENTRAL
1524
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
NCI_THESAURUS
C604
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
DRUG BANK
DB12465
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL51
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
CHEBI
6123
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
SMS_ID
100000082848
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
INN
5087
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
MESH
D007650
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
WIKIPEDIA
KETANSERIN
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
FDA UNII
97F9DE4CT4
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
MERCK INDEX
M6614
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3023188
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
EVMPD
SUB08366MIG
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
CAS
74050-98-9
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
PUBCHEM
3822
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY
RXCUI
6131
Created by admin on Thu Jul 06 23:15:24 UTC 2023 , Edited by admin on Thu Jul 06 23:15:24 UTC 2023
PRIMARY RxNorm
Related Record Type Details
LABELED -> NON-LABELED
TARGET -> INHIBITOR
Binding Assay
IC50
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY