111974-72-2 Usage
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 lookchem of Tian Ye.
Uses
Different sources of media describe the Uses of 111974-72-2 differently. You can refer to the following data:
1. A non-classical antipsychotics.
2. Used as an antipsychotic. Benzothiazepine with mixed serotonin and dopamine receptor antagonistic properties
3. antihypertensive adrenergic receptor blocking agent with selective alpha1- and nonselective beta-adrenergic receptor blocking actions in a single substance.
4. Quetiapine hemifumarate salt has been used as an antagonist for β-arrestin 2 mutant T205M recruitment.
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
Chemical Properties
White Crystalline Solid
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
Hazard
Human systemic effects.
Biochem/physiol Actions
Quetiapine hemifumarate is an atypical antipsychotic, a combined serotonin (5HT2) and dopamine (D2) receptor antagonist.
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].
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
Check Digit Verification of cas no
The CAS Registry Mumber 111974-72-2 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, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 111974-72:
(8*1)+(7*1)+(6*1)+(5*9)+(4*7)+(3*4)+(2*7)+(1*2)=122
122 % 10 = 2
So 111974-72-2 is a valid CAS Registry Number.
InChI:InChI=1S/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+
111974-72-2Relevant articles and documents
An Improved and single pot process for the production of quetiapine hemifumarate substantially free from potential impurities
Niphade, Navnath C.,Mali, Anil C.,Pandit, Bhushan S.,Jagtap, Kunal M.,Jadhav, Sanjay A.,Jachak, Madhukar N.,Mathad, Vijayavitthal T.
, p. 792 - 797 (2009)
An improved and single pot process for the preparation of Quetiapine hemifumarate (1), an antipsychotic drug, free from potential impurities is reported with an overall yield of 80%. The reported process for its preparation suffers from the drawback of producing potential impurities identified as 11-piperazin-1- yldibenzo[b,f][1,4]thiazepine (6), 2-(4-dibenzo[b,f][1,4] thiazepin-11- ylpiperazin-1-yl)ethanol (10), dimer (9), and N-methyl- Nphenyldibenzo[ b,f][1,4]thiazapine-11-amine (14). Elimination of these impurities in the process is achieved by chlorination of 3 followed by in situ condensation of obtained 4 with highly pure 8 and subsequently establishing the pH based workup to obtain free base 2, which is further converted to quetiapine hemifumarate salt free from all these impurities. In this report, different aspects of process development such as scheme selection, optimization of different process parameters, identification, synthesis, origin and control of impurities, and development of an accurate analytical method during the development of a scalable process for quetiapine hemifumarate are discussed.
A [...] synthesis process (by machine translation)
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Paragraph 0058, (2017/02/17)
The present invention discloses a process for synthesizing [...], comprises the following steps: compound of formula (II), C1 - C4 acid mixed, and heated to 80 - 100 °C, adding zinc powder or iron powder, thermal insulation reaction 4 - 6h, shall quetiapine; with the resulting quetiapine fumaric acid salifying, [...], wherein quetiapine with fumaric acid feeding molar ratio of 1: 0.5. The process of the invention has simple operation, high yield, the resulting high purity of the product advantages, and is easy to realize industrial. (by machine translation)
PROCESS FOR THE PREPARATION OF QUETIAPINE FUMARATE
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Page/Page column 10, (2012/04/04)
The present invention relates to an improved process for the preparation of quetiapine and pharmaceutically acceptable salts. It also relates to improved process for the preparation of intermediates of quetiapine.
