| Identification | More | [Name]
Quetiapine fumarate | [CAS]
111974-72-2 | [Synonyms]
2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol hemifumarate
DIBENZOTHIAZEPINOHONEP
ICI-204636
QUETIAPINE FUMARATE
QUETIAPINE HEMIFUMARATE
SEROQUEL
QUETIAPINE FUMARATE, 99+%
Quetiapine Fumarate main intermediates
Seroquel, ICI-204636, Dibenzothiazepinohonep
QUETIAPINE HEMIGUMARTE
Quetiapine·0.5fumaric acid | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C46H54N6O8S2 | [MDL Number]
MFCD03423782 | [Molecular Weight]
883.09 | [MOL File]
111974-72-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
174-176°C | [Fp ]
9℃ | [storage temp. ]
2-8°C | [solubility ]
DMSO: >10mg/mL | [form ]
powder | [color ]
white to off-white | [Usage]
Used as an antipsychotic. Benzothiazepine with mixed serotonin and dopamine receptor antagonistic properties | [Merck ]
14,8039 | [BCS Class]
2 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChIKey]
VRHJBWUIWQOFLF-WLHGVMLRSA-N | [SMILES]
C(/C(=O)O)=C\C(=O)O.C(N1CCN(C2=NC3C=CC=CC=3SC3=CC=CC=C23)CC1)COCCO | [CAS DataBase Reference]
111974-72-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Hazard]
Human systemic effects.
| [Description]
Quetiapine hemifumarate (111974-72-2) is an atypical antipsychotic agent. Antagonist at serotonin (5-HT2) and dopamine (D2) receptors, IC50s=148 and 329 nM respectively.2 Reverses depressive-like behavior and reduces DNA methyltransferase activity induced by maternal deprivation in a rat model.3 Efficacious as a monotherapy in the treatment of posttraumatic stress disorder.4 | [Brand name]
Seroquel (AstraZeneca). | [General Description]
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards | [Biochem/physiol Actions]
Quetiapine hemifumarate is an atypical antipsychotic, a combined serotonin (5HT2) and dopamine (D2) receptor antagonist. | [Synthesis]
General procedure for the synthesis of 2-(2-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy)ethan-1-ol hemifumarate from 11-(piperazin-1-yl)dibenzo[b,f][1,4]thiazepin-1-yl)ethoxy)ethan-1-ol:
Reagents: 16.5 g (44 mmol) of 11-(piperazin-1-yl)dibenzo[b,f][1,4]thiazepine hydrochloride, 7.2 g (58 mmol) of 2-(2-chloroethoxy)ethanol, 28.5 g (270 mmol) of Na2CO3, 270 mg (0.18 mmol) of NaI, 3 g of TBAB, 82.5 mL of toluene.
Steps:
1. add the above reagents to a round-bottomed flask equipped with a magnetic stirrer and a condenser with a calcium chloride drying tube.
2. Place the flask in an oil bath at 105°C and heat under mild reflux conditions.
3. after 24 hours, a Dean-Stark water separator is connected and the azeotropic mixture of water and toluene is distilled.
4. The residue in the flask was filtered and the precipitate (inorganic salt) was washed with a small amount of toluene on a Brinell funnel.
5. Combine the washings with the filtrate and discard the precipitate.
6. 2.6 g (22 mmol) of fumaric acid is added to the filtrate and the mixture is heated to boiling in a heating bath.
7. Remove the flask from the heating bath and continue stirring to precipitate quetiapine hemifumarate crystals.
8. The flask was cooled in an ice bath and the crystalline product was collected by filtration.
9. The resulting solid was recrystallized from 150 ml of ethanol.
Yield: 14.0 g, 72% yield. | [in vitro]
quetiapine has shown affinity for various neurotransmitter receptorsincluding dopamine, serotonin, histamine, and adrenergicreceptors, quetiapine exihibited binding characteristics at the dopamine-2receptorsimilar to those of clozapine [1]. | [in vivo]
in animal models, quetiapine exihibited a preclinical profile suggestive of antipsychotic activity with a reduced tendency to cause extrapyramidal symptoms (eps) and sustained prolactin elevation. quetiapine altered neurotensin neurotransmission and c-fos expression in limbic but not motor brain regions.in humans, quetiapine exhibited linear pharmacokinetics with a mean terminal half-life of 7 hours.the optimal dosing range for quetiapine was 150 to 750 mg/day, and recent results suggested that once-daily dosing might be suitable for some patients [1].quetiapine prevented schizophrenia and depression in hippocampal cell proliferation and bdnf expression caused by chronic restraint stress (crs) in rats in a dose-dependent manner. quetiapine (5 mg/kg) in combination with venlafaxine (2.5 mg/kg) increaseed hippocampal cell proliferation and prevented bdnf decrease in stressed rats, while each of the drugs exerted mild or no effects [2].in rats subjected to chronic-restraint stress, chronic administration of quetiapine attenuated the decrease in levels of brain-derived neurotrophic factor (bdnf) in the hippocampi. the stress-induced suppression of hippocampal neurogenesis was reversed after post-stress administration of quetiapine (10 mg/kg) for 7 or 21 days, evidenced in the numbers of pcreb-positive and brdu-labeled cells that were comparable to those in non-stressed rats but higher than those in the vehicle-treated rats [3]. | [target]
Androgen Receptor | Estrogen receptor | Progestogen receptor | [storage]
+4°C | [References]
1) Ellenbroek et al. (1996); Activity of “seroquel” (ICI 204,636) in animal models for atypical properties of antipsychotics: a comparison with clozapine; Neuropsychopharmacology 15 406
2) Saller and Salama (1993), Seroquel: biochemical profile of a potential atypical antipsychotic; Psychopharmacolgy (Berl) 112 285
3) Ignacio et al. (2017), Quetiapine treatment reverses depressive-like behavior and reduces DNA methyltransferase activity induced by maternal deprivation; Behav. Brain Res. 320 225
4) Villarreal et al. (2016), Efficacy of Quetiapine Monotherapy in Posttraumatic Stress Disorder: A Randomized, Placebo-Controlled Trial; Am. J. Psychiatry 173 1205 |
| Questions And Answer | Back Directory | [Antipsychotics]
Quetiapine fumarate is an antipsychotic, successfully developed by the AstraZeneca United States, it interacts with a variety of neurotransmitter receptors, in the brain, it displays high degree affinity for serotonin (5-HT2) receptor, and it is greater than dopamine D1 and D2 dopamine receptor affinity in the brain. Quetiapine also has high affinity for histamine H1 receptor and adrenergic α1 receptors, and low affinity for α2 receptors, but it basically displays no affinity for cholinergic muscarinic receptors or benzodiazepine receptors . It shows positive results in antipsychotic activity assays such as conditioned avoidance reflex . In clinical, it is mainly used in treatment for adults with severe depression, acute manic episodes of bipolar disorder and schizophrenia of different types . It is not only effective for the positive symptoms of schizophrenia, but also having a certain effect for negative symptoms . It can also alleviate affective symptoms associated with schizophrenia, such as depression, anxiety symptoms and cognitive deficits.
The above information is edited by the chemicalbook of Tian Ye.
| [Chemical properties]
White crystalline powder.
| [Uses]
A non-classical antipsychotics.
|
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Jia Xing Isenchem Co.,Ltd
|
| Telephone: |
0573-85285100 18627885956 |
| Website: |
https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm |
|