111974-69-7 Usage
Uses
Different sources of media describe the Uses of 111974-69-7 differently. You can refer to the following data:
1. antiviral
2. Labelled Quetiapine (Q510000). Used as an antipsychotic.
Brand name
Seroquel (AstraZeneca).
Biological Functions
Quetiapine is a dibenzothiazepine with a brain receptor–binding profile similar to that of clozapine. Quetiapine binds
most effectively to histaminergic H1, adrenergic a1 and a2, and serotonergic 5-HT2A receptors in the brain and has
even lower affinity than clozapine for dopaminergic D2 receptors. Unlike clozapine, however, quetiapine also has
very low affinity for muscarinic receptors.
General Description
Quetiapine, 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol fumarate (2:1,salt) (Seroquel), is a white to off-white crystalline powderthat is moderately water soluble. Quetiapine is rapidly absorbed,and peak plasma levels occur 1 to 2 hours after administration.Food does not appreciably affect the absorptionof quetiapine. The compound is 83% bound to plasma proteinsand it has a mean elimination half-life of 7 hours.Administration of a single dose of 14C-quetiapine showedthat only 1% of the drug was excreted unchanged, with 73%excreted into the urine and approximately 30% excreted inthe feces.Numerous metabolites of quetiapine are known,and the sulfoxide metabolite represents the major metabolitepresent in plasma. This metabolite is pharmacologicallyinactive. The remaining metabolites represent only5% of the total radioactivity found in plasma. The 7-hydroxyand the 7-hydroxy-N-desalkyl are active metabolites, but because of their low concentrations in plasma are not thoughtto contribute to the overall effects of quetiapine. Common side effects associated with quetiapine therapyare orthostatic hypotension and somnolence. These effects are presumably caused by -adrenergic and histamine H1 receptorblockade, respectively. As with other atypical antipsychotics,patients treated with quetiapine should be monitoredfor hyperglycemic symptoms. Also, children and adolescentswith major depressive disorder may experience an increase intheir depression or suicidal tendencies.typical antipsychotics such as chlorpromazine.This findingmay explain the lack of EPS associated with quetiapine.
Clinical Use
Schizophrenia
Mania in bipolar disorder
Depression in bipolar disorder
Side effects
Quetiapine is 100% bioavailable, but first-pass metabolism yields at least
20 metabolites via CYP3A4, with a half-life of approximately 6 hours. Quetiapine is about as effective as haloperidol
in treating the positive symptoms of schizophrenia, but it also manages negative symptoms and induces a lower
incidence of extrapyramidal side effects.
Drug interactions
Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: increased risk of convulsions with
tramadol; enhanced hypotensive and sedative
effects with opioids; increased risk of ventricular
arrhythmias with methadone.
Anti-arrhythmics: increased risk of ventricular
arrhythmias.
Antibacterials: concentration possibly increased by
macrolides - avoid.
Antidepressants: concentration of tricyclics possibly
increased.
Antiepileptics: antagonism of convulsive threshold;
metabolism accelerated by carbamazepine and
phenytoin; concentration possibly increased by
valproate.
Antifungals: concentration possibly increased by
imidazoles and triazoles - avoid.
Antimalarials: manufacturer advises avoid use with
artemether and lumefantrine.
Antipsychotics: possible increased risk of ventricular
arrhythmias with risperidone.
Antivirals: concentration possibly increased by
atazanavir, boceprevir, darunavir, fosamprenavir,
indinavir, lopinavir, ritonavir, saquinavir, telaprevir
and tipranavir - avoid.
Anxiolytics and hypnotics: enhanced sedative effects.
Atomoxetine: increased risk of ventricular
arrhythmias.
Cytotoxics: increased risk of ventricular arrhythmias
with arsenic trioxide.
Grapefruit juice: concentration of quetiapine possibly
increased - avoid.
Metabolism
Quetiapine is extensively metabolised in the liver by
sulfoxidation mediated mainly by the cytochrome P450
isoenzyme CYP3A4 and by oxidation. The primary
metabolite is norquetiapine, which is also eliminated by
CYP3A4. Following the administration of radiolabelled
quetiapine, the parent compound accounted for less than
5% of unchanged drug-related material in the urine or
faeces. Approximately 73% of the radioactivity is excreted
in the urine and 21% in the faeces, mainly as inactive
metabolites.
Check Digit Verification of cas no
The CAS Registry Mumber 111974-69-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,1,9,7 and 4 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 111974-69:
(8*1)+(7*1)+(6*1)+(5*9)+(4*7)+(3*4)+(2*6)+(1*9)=127
127 % 10 = 7
So 111974-69-7 is a valid CAS Registry Number.
InChI:InChI=1/2C21H25N3O2S.C4H4O4/c2*25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21;5-3(6)1-2-4(7)8/h2*1-8,25H,9-16H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+
111974-69-7Relevant articles and documents
Pyrophosphoryl Chloride: A Green, Reductive Chlorination Reagent Utilized in the One-Pot Synthesis of Quetiapine
Mahmoodi,Pourhossein Parizad,Hosseini
, p. 1029 - 1034 (2015)
A one-pot synthesis of quetiapine from dibenzo[b,f][1,4]thiazepin-11(10H)-one and 4-hydroxyethoxy ethyl piperazine (HEEP) in toluene using N,N-dimethylaniline (DMA) and pyrophosphoryl chloride (P2O3Cl4) as a green reductive chlorination agent is described. A significant shortening of reaction times, a nearly quantitative yield, and high atom economy in the product were observed. The simplicity of the reaction, ease of execution, simple workup, and good yields, together with the use of easily accessible starting materials and an environmentally friendly procedure, are hallmarks of this process.
Crystallographic evaluation of the conformation of quetiapine included in β-cyclodextrin
Endo, Tomohiro,Ishihara, Shintaro,Kaga, Mayumi,Kawashima, Yoshiaki,Matsumoto, Takashi,Nagase, Hiromasa,Ogawa, Noriko,Ueda, Haruhisa,Yamamoto, Hiromitsu,Yasunaga, Toshiya
, (2020)
Single-crystal X-ray diffraction and theoretical calculations were conducted for insights into the β-cyclodextrin (β-CD)-quetiapine inclusion complex structure. β-CD and quetiapine form a host–guest inclusion complex at a ratio of 2:1 in which the β-CD molecules form head-to-head dimers with their secondary hydroxyl groups linked by multiple hydrogen bonds. Quetiapine is totally contained within the β-CD cavity and exhibits two kinds of disorder (parts 1 and 2) in opposite directions in the β-CD complex. To clarify the mobility of the guest molecule in the β-CD cavity, theoretical molecular conformational calculations, crystal optimization and crystal energy calculations were conducted using CONFLEX software. The results of theoretical molecular conformation calculations showed that the mobility of quetiapine is restricted because its tricyclic structure is covered by β-CD. The results of crystal energy calculations indicated that the conformation of disorder part 1, which has high occupancy, was more stable.
Synthesis of PEG-Functionalized Amines Using Ruthenium-Catalyzed Hydrogen Borrowing
Rossi, Federico V.,Starr, Jeremy T.,Uccello, Daniel P.,Young, Jennifer A.
, p. 5890 - 5894 (2020)
The polyethylene glycol (PEG) moiety has become increasingly important in medicinal chemistry. Herein, we describe the PEG functionalization of amines via hydrogen borrowing reductive amination. This was accomplished using the [Ru(p-cymene)Cl2]2 catalyst and phosphorus-containing ligand dppf or DPE to yield a variety of PEGylated primary and secondary amine products. Furthermore, we illustrate the utility of this method with the synthesis of quetiapine (Seroquel) in 62percent isolated yield.
Preparation method of quetiapine
-
Paragraph 0011; 0016; 0022-0031, (2021/06/13)
The invention discloses a method for synthesizing quetiapine by using a ruthenium catalyst. 11-[4-[2-(2-hydroxyethoxy) ethyl-1-piperazinyl]]-dibenzo [b, f] [1, 4] sulfur nitrogen is prepared from 11-piperazinyl dibenzo [b, f] [1, 4] sulfur nitrogen and diethylene glycol as raw materials under the catalytic action of a ruthenium catalyst, the product purity is greater than or equal to 95%, and the yield is greater than or equal to 90%. The method has the advantages of mild reaction conditions, high atom utilization rate, high product yield, low cost and environmental friendliness, and is suitable for industrial production, and water is the only by-product.
Nickel-Catalyzed Amination of (Hetero)aryl Halides Facilitated by a Catalytic Pyridinium Additive
Han, Dongyang,Li, Sasa,Xia, Siqi,Su, Mincong,Jin, Jian
supporting information, p. 12349 - 12354 (2020/09/09)
An efficient and operationally simple Ni-catalyzed amination protocol has been developed. This methodology features a simple NiII salt, an organic base and catalytic amounts of both a pyridinium additive and Zn metal. A diverse number of (hetero)aryl halides were coupled successfully with primary and secondary alkyl amines, and anilines in good to excellent yields. Similarly, benzophenone imine gave the corresponding N-arylation product in an excellent yield.