Olanzapine N-Oxide | CAS#174794-02-6 | antipsychotic

MedKoo Cat#: 581003 | Name: Olanzapine N-oxide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Olanzapine N-oxide is a metabolite of Olanzapine. Olanzapine (originally branded Zyprexa) is an antipsychotic medication used to treat schizophrenia and bipolar disorder.

Chemical Structure

Olanzapine N-oxide

CAS#174794-02-6

Theoretical Analysis

MedKoo Cat#: 581003

Name: Olanzapine N-oxide

CAS#: 174794-02-6

Chemical Formula: C17H20N4OS

Exact Mass: 328.1358

Molecular Weight: 328.43

Elemental Analysis: C, 62.17; H, 6.14; N, 17.06; O, 4.87; S, 9.76

Price and Availability

Size	Price	Availability	Quantity
2mg	USD 450.00

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Synonym

Olanzapine N-oxide; Olanzapine N oxide;

IUPAC/Chemical Name

1-Methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazine 1-oxide

InChi Key

LJVNYCDXBXGQIK-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H20N4OS/c1-12-11-13-16(20-7-9-21(2,22)10-8-20)18-14-5-3-4-6-15(14)19-17(13)23-12/h3-6,11,19H,7-10H2,1-2H3

SMILES Code

CC(S1)=CC2=C1NC3=CC=CC=C3N=C2N4CC[N+](C)([O-])CC4

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Olanzapine N-oxide is a metabolite of Olanzapine.

In vitro activity:

This study’s initial hypothesis that olanzapine may enhance temozolomide's anti-tumor activity could be confirmed in U87MG and A172 glioblastoma cell lines. Moreover, treatment with olanzapine alone resulted in a marked anti-proliferative effect on U87MG, A172 and two glioma stem-like cells with IC50 values ranging from 25 to 79.9 µM. In U87MG cells, anchorage-independent growth was dose-dependently inhibited. Reference: J Neurooncol. 2015 Mar;122(1):21-33. https://pubmed.ncbi.nlm.nih.gov/25524815/

In vivo activity:

In experiment 1, the highest dose of chronically administered olanzapine (3 mg/kg) induced significant weight gain accompanied by augmentation of periuterine fat depots, with no changes in locomotor activity. In experiment 2, chronic administration did not alter energy expenditure, whereas, decreased respiratory quotient (RQ). In experiment 3, subcutaneously infused olanzapine evidenced a dose and time-dependent increase of body weight and HF-HS diet consumed. Reference: Psychopharmacology (Berl). 2006 Jul;186(4):561-71. https://pubmed.ncbi.nlm.nih.gov/16758241/

Preparing Stock Solutions

The following data is based on the product molecular weight 328.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Vucicevic L, Misirkic-Marjanovic M, Paunovic V, Kravic-Stevovic T, Martinovic T, Ciric D, Maric N, Petricevic S, Harhaji-Trajkovic L, Bumbasirevic V, Trajkovic V. Autophagy inhibition uncovers the neurotoxic action of the antipsychotic drug olanzapine. Autophagy. 2014;10(12):2362-78. doi: 10.4161/15548627.2014.984270. PMID: 25551567; PMCID: PMC4502661. 2. Karpel-Massler G, Kast RE, Westhoff MA, Dwucet A, Welscher N, Nonnenmacher L, Hlavac M, Siegelin MD, Wirtz CR, Debatin KM, Halatsch ME. Olanzapine inhibits proliferation, migration and anchorage-independent growth in human glioblastoma cell lines and enhances temozolomide's antiproliferative effect. J Neurooncol. 2015 Mar;122(1):21-33. doi: 10.1007/s11060-014-1688-7. Epub 2014 Dec 19. PMID: 25524815. 3. Liu X, Zhang H, Zhang S, Mao W, Liu L, Deng C, Hu CH. Olanzapine-induced decreases of FGF21 in brown adipose tissue via histone modulations drive UCP1-dependent thermogenetic impairment. Prog Neuropsychopharmacol Biol Psychiatry. 2023 Mar 2;122:110692. doi: 10.1016/j.pnpbp.2022.110692. Epub 2022 Dec 9. PMID: 36509252. 4. Coccurello R, Caprioli A, Ghirardi O, Conti R, Ciani B, Daniele S, Bartolomucci A, Moles A. Chronic administration of olanzapine induces metabolic and food intake alterations: a mouse model of the atypical antipsychotic-associated adverse effects. Psychopharmacology (Berl). 2006 Jul;186(4):561-71. doi: 10.1007/s00213-006-0368-5. Epub 2006 May 13. PMID: 16758241.

In vitro protocol:

In vivo protocol:

1. Liu X, Zhang H, Zhang S, Mao W, Liu L, Deng C, Hu CH. Olanzapine-induced decreases of FGF21 in brown adipose tissue via histone modulations drive UCP1-dependent thermogenetic impairment. Prog Neuropsychopharmacol Biol Psychiatry. 2023 Mar 2;122:110692. doi: 10.1016/j.pnpbp.2022.110692. Epub 2022 Dec 9. PMID: 36509252. 2. Coccurello R, Caprioli A, Ghirardi O, Conti R, Ciani B, Daniele S, Bartolomucci A, Moles A. Chronic administration of olanzapine induces metabolic and food intake alterations: a mouse model of the atypical antipsychotic-associated adverse effects. Psychopharmacology (Berl). 2006 Jul;186(4):561-71. doi: 10.1007/s00213-006-0368-5. Epub 2006 May 13. PMID: 16758241.

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Chem Res Toxicol. 2020 Sep 21;33(9):2420-2431. doi: 10.1021/acs.chemrestox.0c00191. Epub 2020 Aug 17. PMID: 32786547. 4: Weston M, Kaserer T, Wu A, Mouravlev A, Carpenter JC, Snowball A, Knauss S, von Schimmelmann M, During MJ, Lignani G, Schorge S, Young D, Kullmann DM, Lieb A. Olanzapine: A potent agonist at the hM4D(Gi) DREADD amenable to clinical translation of chemogenetics. Sci Adv. 2019 Apr 17;5(4):eaaw1567. doi: 10.1126/sciadv.aaw1567. PMID: 31001591; PMCID: PMC6469940. 5: Reddy VP, Jones BC, Colclough N, Srivastava A, Wilson J, Li D. An Investigation into the Prediction of the Plasma Concentration-Time Profile and Its Interindividual Variability for a Range of Flavin-Containing Monooxygenase Substrates Using a Physiologically Based Pharmacokinetic Modeling Approach. Drug Metab Dispos. 2018 Sep;46(9):1259-1267. doi: 10.1124/dmd.118.080648. Epub 2018 Jun 12. PMID: 29895591. 6: Hendrickx S, Uğur DY, Yilmaz IT, Şener E, Van Schepdael A, Adams E, Broeckhoven K, Cabooter D. A sensitive capillary LC-UV method for the simultaneous analysis of olanzapine, chlorpromazine and their FMO-mediated N-oxidation products in brain microdialysates. Talanta. 2017 Jan 1;162:268-277. doi: 10.1016/j.talanta.2016.09.053. Epub 2016 Sep 28. PMID: 27837829. 7: Okubo M, Narita M, Murayama N, Akimoto Y, Goto A, Yamazaki H. Individual differences in in vitro and in vivo metabolic clearances of the antipsychotic drug olanzapine from non-smoking and smoking Japanese subjects genotyped for cytochrome P4502D6 and flavincontaining monooxygenase 3. Hum Psychopharmacol. 2016 Mar;31(2):83-92. doi: 10.1002/hup.2515. Epub 2016 Feb 8. PMID: 26856397. 8: Johnson JT, Everly AG, Kpakima FEF, Detke HC. Postmortem redistribution of olanzapine following intramuscular administration of olanzapine pamoate in dogs. Forensic Sci Int. 2015 Dec;257:353-358. doi: 10.1016/j.forsciint.2015.09.022. Epub 2015 Oct 22. PMID: 26517823. 9: Korprasertthaworn P, Polasek TM, Sorich MJ, McLachlan AJ, Miners JO, Tucker GT, Rowland A. In Vitro Characterization of the Human Liver Microsomal Kinetics and Reaction Phenotyping of Olanzapine Metabolism. Drug Metab Dispos. 2015 Nov;43(11):1806-14. doi: 10.1124/dmd.115.064790. Epub 2015 Sep 1. PMID: 26329789. 10: Söderberg MM, Dahl ML. Pharmacogenetics of olanzapine metabolism. Pharmacogenomics. 2013 Aug;14(11):1319-36. doi: 10.2217/pgs.13.120. PMID: 23930678. 11: Söderberg MM, Haslemo T, Molden E, Dahl ML. Influence of FMO1 and 3 polymorphisms on serum olanzapine and its N-oxide metabolite in psychiatric patients. Pharmacogenomics J. 2013 Dec;13(6):544-50. doi: 10.1038/tpj.2012.47. Epub 2012 Nov 13. PMID: 23147717. 12: Haslemo T, Olsen K, Lunde H, Molden E. Valproic Acid significantly lowers serum concentrations of olanzapine-an interaction effect comparable with smoking. Ther Drug Monit. 2012 Oct;34(5):512-7. doi: 10.1097/FTD.0b013e3182693d2a. PMID: 22972535. 13: Habicht SC, Duan P, Vinueza NR, Fu M, Kenttämaa HI. Liquid chromatography/tandem mass spectrometry utilizing ion-molecule reactions and collision-activated dissociation for the identification of N-oxide drug metabolites. J Pharm Biomed Anal. 2010 Mar 11;51(4):805-11. doi: 10.1016/j.jpba.2009.09.047. Epub 2009 Oct 7. PMID: 19897332. 14: Nagashima S, Shimizu M, Yano H, Murayama N, Kumai T, Kobayashi S, Guengerich FP, Yamazaki H. Inter-individual variation in flavin-containing monooxygenase 3 in livers from Japanese: correlation with hepatic transcription factors. Drug Metab Pharmacokinet. 2009;24(3):218-25. doi: 10.2133/dmpk.24.218. PMID: 19571433; PMCID: PMC4755719. 15: Cashman JR, Zhang J, Nelson MR, Braun A. Analysis of flavin-containing monooxygenase 3 genotype data in populations administered the anti-schizophrenia agent olanzapine. Drug Metab Lett. 2008 Apr;2(2):100-14. doi: 10.2174/187231208784040942. PMID: 19356079. 16: Duan P, Fu M, Gillespie TA, Winger BE, Kenttämaa HI. Identification of aliphatic and aromatic tertiary N-oxide functionalities in protonated analytes via ion/molecule and dissociation reactions in an FT-ICR mass spectrometer. J Org Chem. 2009 Feb 6;74(3):1114-23. doi: 10.1021/jo802001e. PMID: 19133762. 17: Williams JB, Mallorga PJ, Conn PJ, Pettibone DJ, Sur C. Effects of typical and atypical antipsychotics on human glycine transporters. Schizophr Res. 2004 Nov 1;71(1):103-12. doi: 10.1016/j.schres.2004.01.013. PMID: 15374578. 18: Kratzsch C, Peters FT, Kraemer T, Weber AA, Maurer HH. Screening, library- assisted identification and validated quantification of fifteen neuroleptics and three of their metabolites in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization. J Mass Spectrom. 2003 Mar;38(3):283-95. doi: 10.1002/jms.440. PMID: 12644990. 19: Callaghan JT, Bergstrom RF, Ptak LR, Beasley CM. Olanzapine. 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