Sertraline

Base Information

• Chemical Name: Sertraline
• CAS No.: 79617-96-2
• Molecular Formula: C17H17Cl2N
• Molecular Weight: 306.235
• European Community (EC) Number: 616-708-3,642-001-4
• UNII: QUC7NX6WMB
• DSSTox Substance ID: DTXSID6023577
• Nikkaji Number: J33.072H
• Wikipedia: Sertraline
• Wikidata: Q407617
• NCI Thesaurus Code: C61939
• RXCUI: 36437
• Pharos Ligand ID: YUTBHTLKAWT2
• Metabolomics Workbench ID: 38699
• ChEMBL ID: CHEMBL809
• Mol file: 79617-96-2.mol

Synonyms:Altruline;Apo Sertraline;Apo-Sertraline;Aremis;Besitran;Gen Sertraline;Gen-Sertraline;Gladem;Hydrochloride, Sertraline;Lustral;Novo Sertraline;Novo-Sertraline;ratio Sertraline;ratio-Sertraline;Rhoxal sertraline;Rhoxal-sertraline;Sealdin;Sertraline;Sertraline Hydrochloride;Sertraline Hydrochloride (1S-cis)-Isomer;Zoloft

Chemical Property of Sertraline

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 8.68E-34mmHg at 25°C
• Melting Point: 246 - 249oC
• Boiling Point: 416.3 °C at 760 mmHg
• PKA: pKa 9.48±0.04(H2O I > 0)(Approximate)
• Flash Point: 205.6 °C
• PSA: 12.03000
• Density: 1.25 g/cm³
• LogP: 5.57050
• Water Solubility.: <0.1g/L(room temperature)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 305.0738049
• Heavy Atom Count: 20
• Complexity: 322

Purity/Quality:

99% ^*data from raw suppliers

Sertraline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CNC1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl
• Isomeric SMILES: CN[C@H]1CC[C@H](C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl
• Recent ClinicalTrials: Vortioxetine in the Elderly vs. Selective Serotonin Reuptake Inhibitors (SSRIs): a Pragmatic Assessment
• Recent EU Clinical Trials: Antidepressant for the prevention of DEPression following first episode Psychosis trial
• Recent NIPH Clinical Trials: The psychotropic drug dopamine PET study
• Therapeutic Function: Antidepressant
• Biological Functions: Sertraline (Zoloft) has an elimination half-life of 25 hours and can be administered once a day, usually in the morning to avoid insomnia. Sertraline undergoes extensive hepatic metabolism, and doses must be reduced in patients with liver disease. Sertraline may produce more gastrointestinal side effects, such as nausea and diarrhea, than does fluoxetine and is generally thought to be less activating than fluoxetine. It is highly bound to serum proteins (98%) and may alter plasma protein binding of other medications.A 14-day washout period is recommended before starting a MAOI. Sertraline is a weak inhibitor of cytochrome P450 2D6. Intensive therapeutic drug monitoring is indicated when combining sertraline with drugs metabolized by this route that have a narrow therapeutic index, such as the TCAs and the type 1C antiarrhythmics propafenone, encainide, and flecainide.
• Clinical Use: SSRI: Antidepressant Post-traumatic stress disorder Obsessive compulsive disorder
• Drug interactions: Sertraline is not a potent inhibitor of CYP3A4, and because CYP2D6 metabolism is a minor pathway for sertraline, drug–drug interactions with these isoforms is unlikely to be of clinical importance. Sertraline is metabolized by more than one CYP isoform in parallel; therefore, drug interactions or genetic polymorphisms are unlikely to cause clinically significant drug interaction via CYP isoform inhibition. Caution is advised, however, when coadministering sertraline with potential object drugs, especially those with narrow therapeutic indices in elderly patients. For example, sertraline has been shown to reduce the clearance of desipramine and imipramine as a result of CYP2D6 inhibition. Because sertraline is highly protein bound, patients receiving it concurrently with any highly protein-bound drug should be observed for potential adverse effects associated with combined therapy.

Technology Process of Sertraline

There total 104 articles about Sertraline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

sertraline hydrochloride (79559-97-0) → Sertraline (79617-96-2)

Guidance literature:

With sodium hydroxide; In water; toluene; for 0.25h; pH=> 10;

Reference yield: 93.0%

[(1S,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-methyl-amine D(-)mandelate → Sertraline (79617-96-2)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate; for 0.25h; pH=> 10;

Reference yield: 89.0%

benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl(methyl)carbamate (1346228-89-4) → Sertraline (79617-96-2)

Guidance literature:

With hydrogen; In methanol; dichloromethane; water; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jo201794k

upstream raw materials:

cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine

chloroformic acid ethyl ester

norsertraline

methanol

Downstream raw materials:

sertraline p-tosylate

sertraline benzoate

sertraline besylate

sertraline hydrochloride acetic acid solvate

Refernces

• 1、 Chénard, étienne,Cusson, Jean-Philippe,Hanessian, Stephen,Hensienne, Rapha?l. "Catalytic Lewis and Br?nsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes". . p. 292 - 306. Retrieved 2020/06/17.
• 2、 -. "End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives". . . Retrieved 2018/03/24.