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

Olanzapine N-Oxide
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581003

CAS#: 174794-02-6

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 581003
Name: Olanzapine N-Oxide
CAS#: 174794-02-6
Chemical Formula: C17H20N4OS
Exact Mass: 328.14
Molecular Weight: 328.434
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
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 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

More Info:

Product Data:

Product Data

Instruction:

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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:	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.
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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1: 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. PubMed PMID: 26856397.

2: Johnson JT, Everly AG, Kpakima FE, Detke HC. Postmortem redistribution of olanzapine following intramuscular administration of olanzapine pamoate in dogs. Forensic Sci Int. 2015 Dec;257:353-8. doi: 10.1016/j.forsciint.2015.09.022. Epub 2015 Oct 22. PubMed PMID: 26517823.

3: 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. PubMed PMID: 26329789.

4: Söderberg MM, Dahl ML. Pharmacogenetics of olanzapine metabolism. Pharmacogenomics. 2013 Aug;14(11):1319-36. doi: 10.2217/pgs.13.120. Review. PubMed PMID: 23930678.

5: 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. PubMed PMID: 23147717.

6: 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. PubMed PMID: 22972535.

7: 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. PubMed PMID: 19897332.

8: 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. PubMed PMID: 19571433; PubMed Central PMCID: PMC4755719.

9: 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. PubMed PMID: 19356079.

10: 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. PubMed PMID: 19133762.

11: 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. PubMed PMID: 15374578.

12: 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. PubMed PMID: 12644990.

13: Callaghan JT, Bergstrom RF, Ptak LR, Beasley CM. Olanzapine. Pharmacokinetic and pharmacodynamic profile. Clin Pharmacokinet. 1999 Sep;37(3):177-93. Review. PubMed PMID: 10511917.

14: Murphy AT, Lake BG, Bernstein JR, Franklin RB, Gillespie TA. Characterization of olanzapine (LY170053) in human liver slices by liquid chromatography/tandem mass spectrometry. J Mass Spectrom. 1998 Dec;33(12):1237-45. PubMed PMID: 9875525.

15: Mattiuz E, Franklin R, Gillespie T, Murphy A, Bernstein J, Chiu A, Hotten T, Kassahun K. Disposition and metabolism of olanzapine in mice, dogs, and rhesus monkeys. Drug Metab Dispos. 1997 May;25(5):573-83. PubMed PMID: 9152596.

16: Kassahun K, Mattiuz E, Nyhart E Jr, Obermeyer B, Gillespie T, Murphy A, Goodwin RM, Tupper D, Callaghan JT, Lemberger L. Disposition and biotransformation of the antipsychotic agent olanzapine in humans. Drug Metab Dispos. 1997 Jan;25(1):81-93. PubMed PMID: 9010634.

17: Schlicker E, Marr I. The moderate affinity of clozapine at H3 receptors is not shared by its two major metabolites and by structurally related and unrelated atypical neuroleptics. Naunyn Schmiedebergs Arch Pharmacol. 1996 Feb;353(3):290-4. PubMed PMID: 8692283.

18: Ring BJ, Catlow J, Lindsay TJ, Gillespie T, Roskos LK, Cerimele BJ, Swanson SP, Hamman MA, Wrighton SA. Identification of the human cytochromes P450 responsible for the in vitro formation of the major oxidative metabolites of the antipsychotic agent olanzapine. J Pharmacol Exp Ther. 1996 Feb;276(2):658-66. PubMed PMID: 8632334.

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Olanzapine N-Oxide featured