3-(2-(4-((4-Fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-2,4(1H,3H)-quinazolinedione

HCID 156394CAS 76330-73-9

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Basic information

Standard SMILES: O=c1[nH]c2ccccc2c(=O)n1CCN1CCC(C(O)c2ccc(F)cc2)CC1
InChIKey: YOSNEENBUVSRQB-UHFFFAOYSA-N
Molecular formula: C22H24FN3O3
Average molar mass: 397.4 g/mol

Overview

major ketanserin metabolite; structure given in first source

Names & identifiers

Preferred name: 3-(2-(4-((4-Fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-2,4(1H,3H)-quinazolinedione
IUPAC: 3-[2-[4-[(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]ethyl]-1H-quinazoline-2,4-dione
English name: ketanserinol
Molecular weight: 0

Names & synonyms

Ketanserinol76330-73-9Reduced ketanserin2,4(1H,3H)-Quinazolinedione, 3-(2-(4-((4-fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-3-(2-(4-((4-Fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-2,4-(1H,3H)quinazolinedione3-[2-[4-[(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedioneR-46742R 46,7423-(2-(4-((4-Fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-2,4(1H,3H)-quinazolinedioneRefChem:9108993-[2-[4-[(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]ethyl]-1H-quinazoline-2,4-dioneR 46742

Show more names

3-[2-[4-[(4-Fluorophenylcarbonyl)(hydroxy)methyl]piperidin-1-yl]ethyl]-2,4(1H,3H)-quinazolinedione

KETANSERIN_met004KetanserinolReduced ketanserinSCHEMBL431162orb1987073DTXSID70997695CSAITASUWRGAOT-UHFFFAOYSA-NAKOS040746948HY-121208

Database identifiers

CAS: 76330-73-9
PubChem CID: 156394
DTXSID: DTXSID70997695

Properties

Computed structural properties

XLogP: 2.4
Topological polar surface area: 72.9 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 5
Heavy atoms: 29
Formal charge: 0
Complexity: 588

Experimental & physicochemical properties

Collision Cross Section193.56 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

storage temp.: 2 · 2-8°C, protect from light
form: Solid
color: White to off-white

Chemistry & industry

Applications · 2 items

DescriptionKetanserinol is the metabolite of ketanserin, a hypotensive drug with 5-HT2 receptor antagonism. Ketanserin is used to reverse pulmonary hypertension caused by protamine.

UsesKetanserinol (R 46742) is a metabolite of Ketanserin (HY-10562). Ketanserinol is a competitive antagonist of the effects of 5-HT (HY-B1473A) in both arteries. The KB values are 6.5 for large coronary arteries and 6.4 for pulmonary arteries[1].