25332-39-2 Usage
Description
Trazodone hydrochloride, also known as a serotonin uptake inhibitor, is a hydrochloride salt form of trazodone with antidepressant and sedative activities. It is primarily used in the treatment of major depression and serves as a serotonin antagonist and reuptake inhibitor (SARI). Trazodone hydrochloride has anti-anxiety and hypnotic effects, making it suitable for patients suffering from major depressive disorders, anxiety, and insomnia. It is an oral drug that functions by affecting the balance of chemicals (neurotransmitters) within the brain that nerves use to communicate with each other. It is a white to off-white solid and is sold under trade names such as Desyrel and Oleptro.
Uses
1. Used in Pharmaceutical Industry:
Trazodone hydrochloride is used as an antidepressant for the treatment of major depressive disorders, anxiety, and insomnia. It is particularly helpful for geriatric patients with severe agitation and certain depressive disorders associated with insomnia and anxiety.
2. Used in Clinical Toxicology and Forensic Analysis:
Trazodone hydrochloride is used as a certified Snap-N-Spike solution for use in clinical toxicology, forensic analysis, or urine drug testing methods by LC-MS/MS or GC/MS.
3. Used in Treatment of Panic Attacks and Aggressive Behavior:
Trazodone hydrochloride is used as an antihistamine and monoamine reuptake inhibitor for the treatment of panic attacks, aggressive behavior, agoraphobia, and cocaine withdrawal in combination with other drugs.
4. Used in Drug Delivery Systems:
Although not explicitly mentioned in the provided materials, trazodone hydrochloride could potentially be used in drug delivery systems to improve its delivery, bioavailability, and therapeutic outcomes, similar to the application of gallotannin in drug delivery systems.
References
https://en.wikipedia.org/wiki/Trazodone
http://www.medicinenet.com/trazodone/article.htm
https://www.drugbank.ca/drugs/DB00656
http://bodyandhealth.canada.com/drug/getdrug/ratio-trazodone
https://pubchem.ncbi.nlm.nih.gov/compound/62935#section=Top
Therapeutic Function
Tranquilizer
Biochem/physiol Actions
Antidepressant that potentiates the activity of serotonin uptake blockers and has full 5-HT2C serotonin receptor agonist activity. It is metabolized to the 5-HT1 serotonin receptor agonist 1-(3-Chlorophenyl)piperazine.
Clinical Use
Tricyclic-related antidepressant
Drug interactions
Potentially hazardous interactions with other drugs
Alcohol: increased sedative effects.
Antidepressants: avoid concomitant use with
MAOIs and moclobemide.
Antiepileptics: antagonism of anticonvulsant effect;
concentration reduced by carbamazepine.
Antimalarials: manufacturer advises avoid
concomitant use with artemether and lumefantrine
and piperaquine with artenimol.
Antivirals: concentration increased by ritonavir;
increased risk of ventricular arrhythmias with
saquinavir - avoid; concentration possibly increased
by telaprevir.
Metabolism
Trazodone is hepatically metabolised via the cytochrome P450 isoenzyme CYP3A4 by n-oxidation and hydroxylation. The metabolite m-chlorophenylpiperazine is active. Trazodone is excreted in the urine almost entirely in the form of its metabolites.
Check Digit Verification of cas no
The CAS Registry Mumber 25332-39-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,3,3 and 2 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 25332-39:
(7*2)+(6*5)+(5*3)+(4*3)+(3*2)+(2*3)+(1*9)=92
92 % 10 = 2
So 25332-39-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H22ClN5O.ClH/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25;/h1-3,5-7,9,15H,4,8,10-14H2;1H
25332-39-2Relevant articles and documents
Microwave-assisted synthesis of trazodone and its derivatives as new 5-HT1A ligands: Binding and docking studies
Jaskowska, Jolanta,Zar eba, Przemys?aw,Sliwa, Pawe?,Pindelska, Edyta,Sata?a, Grzegorz,Majka, Zbigniew
, (2019/05/01)
Trazodone, a well-known antidepressant drug widely used throughout the world, works as a 5-hydroxytryptamine (5-HT2) and α1-adrenergic receptor antagonist and a serotonin reuptake inhibitor. Our research aimed to develop a new method for the synthesis of trazodone and its derivatives. In the known methods of the synthesis of trazodone and its derivatives, organic and toxic solvents are used, and the synthesis time varies from several to several dozen hours. Our research shows that trazodone and its derivatives can be successfully obtained in the presence of potassium carbonate as a reaction medium in the microwave field in a few minutes. As a result of the research work, 17 derivatives of trazodone were obtained, including compounds that exhibit the characteristics of 5-HT1A receptor ligands. Molecular modeling studies were performed to understand the differences in the activity toward 5-HT1A and 5-HT2A receptors between ligand 10a (2-(6-(4-(3-chlorophenyl)piperazin-1-yl)hexyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one) (5-HT1A Ki = 16 nM) and trazodone. The docking results indicate the lack of the binding of ligand 10a to 5-HT2AR, which is consistent with the in vitro studies. On the other hand, the docking results for the 5-HT1A receptor indicate two possible binding modes. Crystallographic studies support the hypothesis of an extended conformation.
Preparation method of trazodone hydrochloride
-
Paragraph 0046; 0047, (2016/12/01)
The invention is applicable to the field of chemistry and chemical engineering and provides a preparation method of trazodone hydrochloride. The preparation method comprises the following steps: mixing N-(3-chloro-phenyl)-N'-(3-chloropropyl)-piperazine hydrochloride and 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one in a solvent; adding an alkali, and heating and reflowing; carrying out heat filtering into a reaction system, adding alkali liquid and heating and reflowing again in sequence; crystallizing to obtain trazodone; taking the trazodone to react with hydrochloric acid to obtain the trazodone hydrochloride. According to the preparation method of the trazodone hydrochloride, provided by the invention, the total yield of the product is improved, and the content of an impurity N-(3-chloro-phenyl)-N'-(3-chloropropyl)-piperazine is remarkably reduced, so that the industry limitation requirements can be directly met. The preparation method has simple flow steps so that the production cost is reduced; the process is stable and industrial production can be carried out.
TRAZODONE AND TRAZODONE HYDROCHLORIDE IN PURIFIED FORM
-
Page/Page column 13-16, (2009/04/25)
A process of production of trazodone or trazodone hydrochloride that comprises the steps of: (a) preparing an organic phase comprising trazodone in at least one organic solvent; (b) preparing an aqueous phase comprising at least one basic compound; (c) mixing said aqueous phase with said organic phase; (d) heating at a temperature o at least 40°C for at least 30 minutes; (e) recovering said trazodone; and, optionally, (f) treating said trazodone with hydrochloric acid to obtain trazodone hydrochloride. Trazodone or trazodone hydrochloride comprising less than 15 ppm of alkylating substances, and a pharmaceutical composition comprising said trazodone hydrochloride.
