Olanzapine
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MedKoo CAT#: 318383

CAS#: 132539-06-1 (free base)

Description: Olanzapine is an atypical antipsychotic. It is approved by the U.S. Food and Drug Administration (FDA) for the treatment of schizophrenia and bipolar disorder. Olanzapine is structurally similar to clozapine and quetiapine. It is a dopamine antagonist and is classified as a thienobenzodiazepine.


Chemical Structure

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Olanzapine
CAS# 132539-06-1 (free base)

Theoretical Analysis

MedKoo Cat#: 318383
Name: Olanzapine
CAS#: 132539-06-1 (free base)
Chemical Formula: C17H20N4S
Exact Mass: 312.14
Molecular Weight: 312.433
Elemental Analysis: C, 65.35; H, 6.45; N, 17.93; S, 10.26

Price and Availability

Size Price Availability Quantity
1g USD 350
2g USD 550
5g USD 950
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Related CAS #: 132539-06-1 (free base); 783334-36-1 (HCl)  

Synonym: LY-170052, LY170052, LY 170052, Olanzapine, Zyprexa, Zolafren

IUPAC/Chemical Name: 2-methyl-4-(4-methylpiperazin-1-yl)-5H-thieno[3,2-c][1,5]benzodiazepine

InChi Key: WXPNDRBBWZMPQG-UHFFFAOYSA-N

InChi Code: 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/h3-6,11,18H,7-10H2,1-2H3

SMILES Code: CN1CCN(C2=C(C=C(C)S3)C3=NC4=CC=CC=C4N2)CC1

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, not in water

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:
Biological target: Olanzapine (LY170053) is a selective, orally active monoaminergic antagonist with high affinity binding to serotonin H1, 5HT2A/2C, 5HT3, 5HT6 (Ki=7, 4, 11, 57, and 5 nM, respectively), dopamine D1-4 (Ki=11 to 31 nM), muscarinic M1-5 (Ki=1.9-25 nM), and adrenergic α1 receptor (Ki=19 nM).
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 64.01
DMSO 32.3 103.41
DMSO:PBS (pH 7.2) (1:1) 0.5 1.60
Ethanol 8.0 25.61

Preparing Stock Solutions

The following data is based on the product molecular weight 312.43 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.

Recalculate based on batch purity %
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: Fonte C, Fatigoni S, Roila F. A review of olanzapine as an antiemetic in chemotherapy-induced nausea and vomiting and in palliative care patients. Crit Rev Oncol Hematol. 2015 Aug;95(2):214-21. doi: 10.1016/j.critrevonc.2015.02.010. Epub 2015 Mar 5. Review. PubMed PMID: 25779971.

2: Ennis ZN, Damkier P. Pregnancy exposure to olanzapine, quetiapine, risperidone, aripiprazole and risk of congenital malformations. A systematic review. Basic Clin Pharmacol Toxicol. 2015 Apr;116(4):315-20. doi: 10.1111/bcpt.12372. Epub 2015 Jan 28. Review. PubMed PMID: 25536446.

3: Choi YJ. Efficacy of adjunctive treatments added to olanzapine or clozapine for weight control in patients with schizophrenia: a systematic review and meta-analysis. ScientificWorldJournal. 2015;2015:970730. doi: 10.1155/2015/970730. Epub 2015 Jan 13. Review. PubMed PMID: 25664341; PubMed Central PMCID: PMC4310265.

4: Luedecke D, Schöttle D, Karow A, Lambert M, Naber D. Post-injection delirium/sedation syndrome in patients treated with olanzapine pamoate: mechanism, incidence, and management. CNS Drugs. 2015 Jan;29(1):41-6. doi: 10.1007/s40263-014-0216-9. Review. PubMed PMID: 25424243.

5: Flank J, Sung L, Dvorak CC, Spettigue W, Dupuis LL. The safety of olanzapine in young children: a systematic review and meta-analysis. Drug Saf. 2014 Oct;37(10):791-804. doi: 10.1007/s40264-014-0219-y. Review. PubMed PMID: 25145624.

6: Kartashov VA, Chernova LV. [The detection of quentiapine and olanzapine in the biological objects]. Sud Med Ekspert. 2014 Sep-Oct;57(5):47-52. Review. Russian. PubMed PMID: 25764884.

7: Cristancho MA, Thase ME. Drug safety evaluation of olanzapine/fluoxetine combination. Expert Opin Drug Saf. 2014 Aug;13(8):1133-41. doi: 10.1517/14740338.2014.933804. Epub 2014 Jun 27. Review. PubMed PMID: 24972823.

8: Vella T, Mifsud J. Interactions between valproic acid and quetiapine/olanzapine in the treatment of bipolar disorder and the role of therapeutic drug monitoring. J Pharm Pharmacol. 2014 Jun;66(6):747-59. doi: 10.1111/jphp.12209. Epub 2014 Jan 7. Review. PubMed PMID: 24392714.

9: Hocking CM, Kichenadasse G. Olanzapine for chemotherapy-induced nausea and vomiting: a systematic review. Support Care Cancer. 2014 Apr;22(4):1143-51. doi: 10.1007/s00520-014-2138-y. Epub 2014 Feb 13. Review. PubMed PMID: 24522741.

10: Wang SY, Yang ZJ, Zhang L. Olanzapine for preventing nausea and vomiting induced by moderately and highly emetogenic chemotherapy. Asian Pac J Cancer Prev. 2014;15(22):9587-92. Review. PubMed PMID: 25520071.

11: Brafford MV, Glode A. Olanzapine: an antiemetic option for chemotherapy-induced nausea and vomiting. J Adv Pract Oncol. 2014 Jan;5(1):24-9. Review. PubMed PMID: 25032030; PubMed Central PMCID: PMC4093458.

12: Zhao J, Ou J, Xue H, Liu L, Montgomery W, Treuer T. Clinical utility of orally disintegrating olanzapine in Chinese patients with schizophrenia: a review of effectiveness, patient preference, adherence, and other properties. Neuropsychiatr Dis Treat. 2014 Feb 19;10:355-9. doi: 10.2147/NDT.S39055. eCollection 2014. Review. PubMed PMID: 24600225; PubMed Central PMCID: PMC3933704.

13: Navari RM. Olanzapine for the prevention and treatment of chronic nausea and chemotherapy-induced nausea and vomiting. Eur J Pharmacol. 2014 Jan 5;722:180-6. doi: 10.1016/j.ejphar.2013.08.048. Epub 2013 Oct 21. Review. PubMed PMID: 24157985.

14: Xue HB, Liu L, Zhang H, Montgomery W, Treuer T. Olanzapine in Chinese patients with schizophrenia or bipolar disorder: a systematic literature review. Neuropsychiatr Dis Treat. 2014 May 16;10:841-64. doi: 10.2147/NDT.S58096. eCollection 2014. Review. PubMed PMID: 24876777; PubMed Central PMCID: PMC4037301.

15: van der Zwaal EM, Janhunen SK, la Fleur SE, Adan RA. Modelling olanzapine-induced weight gain in rats. Int J Neuropsychopharmacol. 2014 Jan;17(1):169-86. doi: 10.1017/S146114571300093X. Epub 2013 Oct 8. Review. PubMed PMID: 24103788.

16: Kansagra A, Patel S, Wilcox SR. Prolonged hypothermia due to olanzapine in the setting of renal failure: a case report and review of the literature. Ther Adv Psychopharmacol. 2013 Dec;3(6):335-9. doi: 10.1177/2045125313490304. Review. PubMed PMID: 24294486; PubMed Central PMCID: PMC3840808.

17: Schöttle D, Kuhnigk O, Naber D. Drug safety evaluation of olanzapine pamoate. Expert Opin Drug Saf. 2013 Nov;12(6):897-903. doi: 10.1517/14740338.2013.832753. Epub 2013 Sep 12. Review. PubMed PMID: 24024627.

18: Lee HB, Yoon BH, Kwon YJ, Woo YS, Lee JG, Kim MD, Bahk WM. The efficacy and safety of switching to ziprasidone from olanzapine in patients with bipolar I disorder: an 8-week, multicenter, open-label study. Clin Drug Investig. 2013 Oct;33(10):743-53. doi: 10.1007/s40261-013-0120-y. Review. PubMed PMID: 23990283.

19: Schulz C, Haight RJ. Safety of olanzapine use in adolescents. Expert Opin Drug Saf. 2013 Sep;12(5):777-82. doi: 10.1517/14740338.2013.815164. Epub 2013 Jul 22. Review. PubMed PMID: 23876012.

20: Perera V, Gross AS, Polasek TM, Qin Y, Rao G, Forrest A, Xu J, McLachlan AJ. Considering CYP1A2 phenotype and genotype for optimizing the dose of olanzapine in the management of schizophrenia. Expert Opin Drug Metab Toxicol. 2013 Sep;9(9):1115-37. doi: 10.1517/17425255.2013.795540. Epub 2013 May 4. Review. PubMed PMID: 23641727.