Olanzapine

Base Information

• Chemical Name: Olanzapine
• CAS No.: 132539-06-1
• Molecular Formula: C17H20N4S
• Molecular Weight: 312.439
• Hs Code.: 29349990
• Mol file: 132539-06-1.mol

Synonyms:2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno(2,3-b)(1,5)benzodiazepine;Olansek;10H-Thieno(2,3-b)(1,5)benzodiazepine, 2-methyl-4-(4-methyl-1-piperazinyl)-;Symbyax;Zyprexa (TN);Olanzapine [USAN:INN];2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepine;Olanzapine;

Chemical Property of Olanzapine

Chemical Property:

• Appearance/Colour: yellowish crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 195 °C
• Refractive Index: 1.709
• Boiling Point: 476.035 °C at 760 mmHg
• PKA: 7.78±0.20(Predicted)
• Flash Point: 241.697 °C
• PSA: 59.11000
• Density: 1.32 g/cm³
• LogP: 2.88860
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: >15mg/mL

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Olanzapine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn,F
• Hazard Codes: Xi,Xn,F
• Statements: 36/38-36-20/21/22-11
• Safety Statements: 26-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Used to control schizophrenia, bipolar mania and other diseases A serotonin (5-HT2) and dopamine (D1/D2) receptor antagonist with anticholinergic activity. Antipsychotic. intermediate for Imidacloprid, Indobufen, Nitroguanidine, Nalorphine, Tazarotene, Trovafloxacin anti-ulcer, gastrointestinal-emptying agent enhances motility in the upper gastrointestinal tract
• Production method: 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzo-diazepin-hydrochloride and N-methylpiperazine in toluene and dimethylsulfoxide , reflux under nitrogen for 20h, to obtain olanzapine.
• Description: O lanzapine is classed as an atypical antipsychotic and is considered a firstline agent in the management of newly diagnosed psychosis. It has a similar mechanism of action to classical antipsychotics but with a lower incidence of adverse events. O lanzapine rarely produces hypotension and has less potential for QT prolongation. It is used in the management of delirium in ICU. Zyprexa was launched in Canada, Germany, the UK and US as an antipsychotic agent. Prepared in three steps via the intermediate diazepinone, it is an atypical antipsychotic with a high affinity for dopaminergic and serotonergic receptors. Specifically, olazapine is a potent 5-HT2/D2 antagonist with anticholinergic activity. It has a greater antagonistic effect at 5-HT2a than at dopamine D2 receptors and in vivo is clozapine-like. Thus it is less likely to produce extrapyramidal side effects and does not produce any granulocytopenia. Its 10 metabolic products are all inactive.
• Therapeutic Function: Antipsychotic
• Clinical Use: The thienobenzodiazepine olanzapine is an effective atypical antipsychotic agent that is close in structure to clozapine but has a somewhat different neuropharmacological profile, in that it is a more potent antagonist at dopamine D2 and, especially, serotonin 5-HT2A receptors. Olanzapine is well absorbed after oral administration and is metabolized mainly by CYP1A2 to inactive metabolites, with a variable half-life of approximately 20 to 50 hours.
• 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 ciprofloxacin. Antidepressants: fluvoxamine increases concentration of olanzapine; increased concentration of tricyclics. Antiepileptics: antagonism (convulsive threshold lowered); carbamazepine increases metabolism of olanzapine; increased risk of neutropenia with valproate. Antimalarials: avoid with artemether/lumefantrine. Antipsychotics: increased risk of ventricular arrhythmias with risperidone. Antivirals: concentration reduced by ritonavir - consider increasing olanzapine dose. Anxiolytics and hypnotics: increased sedative effects; increased risk of hypotension, bradycardia and respiratory depression with IM olanzapine and parenteral benzodiazepines. Atomoxetine: increased risk of ventricular arrhythmias. Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide.

Technology Process of Olanzapine

There total 43 articles about Olanzapine 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: 100.0%

2-methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine acetic acid monosolvate → zyprexa (132539-06-1)

Guidance literature:

at 65 - 70 ℃; for 18h; Vacuo;

Reference yield: 99.0%

N-desmethyl olanzapine (161696-76-0) + methyl iodide (74-88-4) → zyprexa (132539-06-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 2h; Product distribution / selectivity;

Reference yield: 92.5%

1-methyl-piperazine (109-01-3) + 4-amino-2-methyl-10H-thiene [2,3-b][1,5]-benzodiazepine hydrochloride (138564-60-0) → zyprexa (132539-06-1)

Guidance literature:

In ethanol; dimethyl sulfoxide; at 100 - 130 ℃; Solvent; Temperature;

upstream raw materials:

1-methyl-piperazine

4-amino-2-methyl-10H-thieno[2,3-b][1,5]benzodiazepine hydrochloride

ortho-nitrofluorobenzene

2-(2-nitroanilino)-5-methylthiophene-3-carbonitrile

Downstream raw materials:

Olanzapine N-Oxide

C₇H₆O₃*C₁₇H₂₀N₄S

C₃₃H₃₃N₅O₂S₂

C₃₃H₃₂BrN₅O₂S₂

Refernces

• 1、 Shevchenko,Nagaev,Kuznetsov,Polunin,Zozulya,Myasoedov. "A synthesis of tritium-labeled olanzapine". . p. 378 - 382. Retrieved 2005.
• 2、 -. "A method of improving the crystal form II olanzapine and method". Paragraph 0050-0051; 0053; 0055. . Retrieved 2018/03/01.
• 3、 -. "Method of manufacturing olanzapine II type". Paragraph 0045-0050. . Retrieved 2018/10/16.