Product Name

  • Name

    Ketanserin

  • EINECS 277-680-2
  • CAS No. 74050-98-9
  • Article Data4
  • CAS DataBase
  • Density 1.281 g/cm3
  • Solubility DMF: 10 mg/mL, clear, colorless
  • Melting Point 227-235 °C
  • Formula C22H22FN3O3
  • Boiling Point
  • Molecular Weight 395.433
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 74050-98-9 (Ketanserin)
  • Hazard Symbols
  • Synonyms Ketanserine [INN-French];3-[2-[4-(4-fluorobenzoyl)-1-piperidyl]ethyl]-1H-quinazoline-2,4-dione;Ketanserinum [INN-Latin];R 41468;Ketanserin (USAN);Ketanserina [INN-Spanish];2,4(1H,3H)-Quinazolinedione, 3-(2-(4-(4-fluorobenzoyl)-1-piperidinyl)ethyl)-;R 41,468;Ketanserin [USAN:BAN:INN];3-(2-(4-(p-Fluorobenzoyl)piperidino)ethyl)-2,4-(1H,3H)-quinazolinedione;
  • PSA 75.17000
  • LogP 2.36170

Synthetic route

(4-fluorophenyl)-piperidin-4-ylmethanone
56346-57-7

(4-fluorophenyl)-piperidin-4-ylmethanone

3-(2-chloroethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline
5081-87-8

3-(2-chloroethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
With sodium carbonate In butanone for 24h; Reflux;86%
(4-fluorophenyl)-piperidin-4-ylmethanone
56346-57-7

(4-fluorophenyl)-piperidin-4-ylmethanone

2,3-dihydro-5H-oxazolo<2,3-b>quinazolin-5-one
52727-44-3

2,3-dihydro-5H-oxazolo<2,3-b>quinazolin-5-one

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
In neat (no solvent) at 110℃;85%
In toluene for 40h; Reflux;80%
4-(4-fluorobenzoyl)piperidine hydrochloride
25519-78-2

4-(4-fluorobenzoyl)piperidine hydrochloride

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

3-(2-chloroethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline
5081-87-8

3-(2-chloroethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
With sodium carbonate In water2,2 parts (27%)
...Expand
2,4-Dioxo-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinazoline
1207-75-6

2,4-Dioxo-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinazoline

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / chloroform / 4 h / Reflux
2: sodium carbonate / butanone / 24 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride / 1,2-dichloro-ethane / 2 h / 20 - 80 °C
2: sodium carbonate / acetonitrile / 7 h / 85 °C
3: toluene / 40 h / Reflux
View Scheme
4-(4-fluorobenzoyl)piperidine hydrochloride
25519-78-2

4-(4-fluorobenzoyl)piperidine hydrochloride

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / methanol / 4 h / 20 °C
2: neat (no solvent) / 110 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate / methanol / 4 h / 20 °C
2: sodium carbonate / butanone / 24 h / Reflux
View Scheme
2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: chloroform / 0.5 h / 50 °C
1.2: 4 h / 150 °C
2.1: sodium carbonate / butanone / 24 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: chloroform / 50 °C
2: chloroform / 4 h / 150 °C
3: thionyl chloride / chloroform / 4 h / Reflux
4: sodium carbonate / butanone / 24 h / Reflux
View Scheme
ethyl (2-ethoxycarbonyl)phenylcarbamate
108890-73-9

ethyl (2-ethoxycarbonyl)phenylcarbamate

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: chloroform / 4 h / 150 °C
2: thionyl chloride / chloroform / 4 h / Reflux
3: sodium carbonate / butanone / 24 h / Reflux
View Scheme
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate / tetrahydrofuran; water / 12 h / -5 - 20 °C
2: 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 140 °C
3: thionyl chloride / 1,2-dichloro-ethane / 2 h / 20 - 80 °C
4: sodium carbonate / acetonitrile / 7 h / 85 °C
5: toluene / 40 h / Reflux
View Scheme
methyl 2-((ethoxycarbonyl)amino)benzoate
83846-67-7

methyl 2-((ethoxycarbonyl)amino)benzoate

ketanserine
74050-98-9

ketanserine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 140 °C
2: thionyl chloride / 1,2-dichloro-ethane / 2 h / 20 - 80 °C
3: sodium carbonate / acetonitrile / 7 h / 85 °C
4: toluene / 40 h / Reflux
View Scheme
ketanserine
74050-98-9

ketanserine

tartaric acid
87-69-4

tartaric acid

ketanserin tartrate
83846-83-7, 97987-92-3, 121322-28-9, 129046-76-0

ketanserin tartrate

Conditions
ConditionsYield
In ethanol100%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

2,3,7,8-tetrafluorothianthrene-S-oxide

2,3,7,8-tetrafluorothianthrene-S-oxide

ketanserine
74050-98-9

ketanserine

C34H25F5N3O3S2(1+)*BF4(1-)

C34H25F5N3O3S2(1+)*BF4(1-)

Conditions
ConditionsYield
With 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction;60%
...Expand
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

2,3,7,8-tetrafluorothianthrene-S-oxide

2,3,7,8-tetrafluorothianthrene-S-oxide

ketanserine
74050-98-9

ketanserine

C34H25F5N3O3S2(1+)*BF4(1-)

C34H25F5N3O3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; 2,3,7,8-tetrafluorothianthrene-S-oxide; ketanserine With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 2h;
Stage #2: sodium tetrafluoroborate In dichloromethane; water		60%
...Expand
ethereal hydrogen chloride

ethereal hydrogen chloride

ketanserine
74050-98-9

ketanserine

2-chloro-N,N-dimethylacetamide
2675-89-0

2-chloro-N,N-dimethylacetamide

2-[3-{2-[4-(4-Fluorobenzoyl)-1-piperidinyl]ethyl}-2,4-dioxo-3,4-dihydro-1(2H)-quinazolinyl]-N,N-dimethylacetamide hydrochloride
298696-31-8

2-[3-{2-[4-(4-Fluorobenzoyl)-1-piperidinyl]ethyl}-2,4-dioxo-3,4-dihydro-1(2H)-quinazolinyl]-N,N-dimethylacetamide hydrochloride

Conditions
ConditionsYield
With NaH In N,N-dimethyl-formamide; mineral oil
...Expand
ketanserine
74050-98-9

ketanserine

Ketanserinol

Ketanserinol

Conditions
ConditionsYield
With sodium borohydrid In methanol; water

Ketanserin History

Ketanserin (74050-98-9) was discovered at Janssen Pharmaceutica in 1980.

Ketanserin Standards and Recommendations

Loss on drying: ≤0.5% 0.3%
Assay: ≥97.0% 98.1%

Ketanserin Specification

The IUPAC name of Ketanserin is 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-1H-quinazoline-2,4-dione. With the CAS registry number 74050-98-9, it is also named as 2,4(1H,3H)-Quinazolinedione, 3-(2-(4-(4-fluorobenzoyl)-1-piperidinyl)ethyl)-. The classification codes are Antihypertensive agents; Cardiovascular Agents; Hematologic Agents; Neurotransmitter Agents; Platelet aggregation inhibitors; Serotonin Agents; Serotonin antagonist; Serotonin antagonists. It is white to light yellow crystalline powder.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.36; (4)ACD/LogD (pH 7.4): 3.046; (5)ACD/BCF (pH 5.5): 1.891; (6)ACD/BCF (pH 7.4): 91.702; (7)ACD/KOC (pH 5.5): 13.047; (8)ACD/KOC (pH 7.4): 632.69; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.593; (13)Molar Refractivity: 104.594 cm3; (14)Molar Volume: 308.689 cm3; (15)Polarizability: 41.464×10-24 cm3; (16)Surface Tension: 49.583 dyne/cm; (17)Rotatable Bond Count: 5; (18)Tautomer Count: 10; (19)Exact Mass: 395.16452; (20)MonoIsotopic Mass: 395.16452; (21)Topological Polar Surface Area: 69.7; (22)Heavy Atom Count: 29.

Uses of Ketanserin: It is drug with affinity for multiple GPCR receptors. It has been used to reverse hypertension caused by protamine (which in turn was administered to reverse the effects of heparin overdose). It also has been used in cardiac surgery. With tritium (3H) radioactively labeled Ketanserin is used as a radioligand for the serotonin 5-HT2A receptor, e.g. in receptor binding assays and autoradiography. Additionally, the drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation.

People can use the following data to convert to the molecule structure.
1. SMILES:c1ccc2c(c1)c(=O)n(c(=O)[nH]2)CCN3CCC(CC3)C(=O)c4ccc(cc4)F
2. InChI:InChI=1/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)

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