5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),5,8,11,13-hexaene

• ChemBase ID: 73043
• Molecular Formular: C17H20N4S
• Molecular Mass: 312.4325
• Monoisotopic Mass: 312.14086766
• SMILES: N1c2c(C(=Nc3c1cccc3)N1CCN(CC1)C)cc(s2)C
• Canonical SMILES: CN1CCN(CC1)C1=Nc2ccccc2Nc2c1cc(s2)C
• InChI: InChI=1S/C17H20N4S/c1-12-11-13-16(21-9-7-20(2)8-10-21)18-14-5-3-4-6-15(14)19-17(13)22-12/h3-6,11,19H,7-10H2,1-2H3
• InChIKey: KVWDHTXUZHCGIO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),5,8,11,13-hexaene; 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^3,^7]tetradeca-1(14),3(7),5,8,10,12-hexaene; 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),5,8,11,13-hexaene
• IUPAC Traditional name: 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),5,8,11,13-hexaene; zyprexa; 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),5,8,11,13-hexaene; 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^3,^7]tetradeca-1(14),3(7),5,8,10,12-hexaene
• Synonyms: Zyprexa; Zalasta; Zolafren; Olzapin; Oferta; Olanzapine; 2-Methyl-4-(4-methyl-1-piperazinyl)- 10H-thieno[2,3-b][1,5]benzodiazepine; LY-170053; Olanzapine; 2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine; Integrol; LY 170053; Lanzac; Oleanz; Oliza; Oltal; Zyprexa Zydis; 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),5,8,11,13-hexaene; 2-Methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepine

Database IDs

• CAS Number: 132539-06-1
• MDL Number: MFCD00866702
• Beilstein Number: 7655141
• PubChem SID: 162037963
• PubChem CID: 4585

CALCULATED PROPERTIES

• Acid pKa: 14.174461
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.2482201
• LogD (pH = 7.4): 2.9497752
• Log P: 3.388495
• Molar Refractivity: 93.8737 cm^3
• Polarizability: 34.417046 Å^3
• Polar Surface Area: 30.87 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetronitrile; DMSO; DMSO: >15 mg/mL; Methanol
• Apperance: yellow powder; Yellow Solid
• Melting Point: 195°C
• Hydrophobicity(logP): 3.009

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H413
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: 5HT(2) and dopamine D2 receptor antagonist

Product Information

• Purity: ≥98% (HPLC); 95%; 95+%
• Salt Data: Free Base
• Application(s): Antipsychotic agent; Used in the treatment of schizophrenia and bipolar disorder
• Empirical Formula (Hill Notation): C17H20N4S

DETAILS

Selleck Chemicals - S2493

Research Area: Cardiovascular Disease
Biological Activity:
Olanzapine(Zyprexa) is a high affinity for 5-HT2 serotonin and D2 dopamine receptor antagonist. It has a higher affinity for 5-HT2 serotonin receptors than D2 dopamine receptors. Like most atypical antipsychotics, compared to the older typical ones, olanzapine has a lower affinity for histamine, cholinergic muscarinic and alpha adrenergic receptors. Olanzapine also exhibits weak affinity for GABAA, BZD receptor site which may contribute slightly to its sedating properties. Antagonizing H1 histamine receptors causes sedation and may cause weight gain, although antagonistic actions at 5-HT2C receptors have also been implicated in weight gain. [1]

Sigma Aldrich - O1141

Biochem/physiol Actions
Olanzapine is a 5-HT2 serotonin and D1/D2 dopamine receptor antagonist.

Toronto Research Chemicals - O253750

A serotonin (5-HT2) and dopamine (D1/D2) receptor antagonist with anticholinergic activity. Antipsychotic.

REFERENCES

• http://en.wikipedia.org/wiki/Olanzapine
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• Baldwin, D.S. and Montgomery, S.A.: Int. Clin. Psychopharmacol., 10, 239 (1993)
• Tohen, M., et al.: Am. J. Psychiatry, 156, 702 (1999)
• Eur. Pat., 1991, Lilly, 454 436; CA, 116, 83703u, (synth, pharmacol)
• Moore, N.A. et al., J. Pharmacol. Exp. Ther., 1992, 262, 545, (pharmacol)
• Fulle, R.W. et al., Res. Commun. Chem. Pathol. Pharmacol., 1992, 77, 87, (pharmacol)
• Fulton, B. et al., Drugs, 1997, 53, 281-298, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 683
• Bhana, N. et al., Drugs, 2001, 61, 111-161, (rev)