Quetiapine hemifumarate
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MedKoo CAT#: 318598

CAS#: 111974-72-2 (hemifumarate)

Description: Quetiapine, also known as ICI 204636, is an antipsychotic agent. It targets the serotonin 5-HT2 receptor, histamine H1 receptor, adreneragic alpha1 and alpha2 rectors as well as the dopamine D1 and D2 receptors. It is used in the treatment of schizophrenia, bipolar disorder and depressive disorder.

Chemical Structure

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Quetiapine hemifumarate
CAS# 111974-72-2 (hemifumarate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318598
Name: Quetiapine hemifumarate
CAS#: 111974-72-2 (hemifumarate)
Chemical Formula: C46H54N6O8S2
Exact Mass: 0.00
Molecular Weight: 441.540
Elemental Analysis: C, 62.56; H, 6.16; N, 9.52; O, 14.49; S, 7.26

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
2g USD 450 2 Weeks
5g USD 750 2 Weeks
10g USD 1250 2 Weeks
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Related CAS #: 111974-72-2 (hemifumarate)   111974-69-7 (free base)    

Synonym: ICI 204,636; IC-204,636; ICI204,636; ICI-204636; ICI 204636; ICI204636; Quetiapine Fumarate; Quetiapine hemifumarate; Seroquel XR.

IUPAC/Chemical Name: 2-(2-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy)ethan-1-ol; fumarate (2:1)

InChi Key: ZTHJULTYCAQOIJ-WXXKFALUSA-N

InChi Code: InChI=1S/2C21H25N3O2S.C4H4O4/c2*25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21;5-3(6)1-2-4(7)8/h2*1-8,25H,9-16H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+

SMILES Code: OC(/C=C/C(O)=O)=O.OCCOCCN(CC1)CCN1C2=NC(C=CC=C3)=C3SC4=C2C=CC=C4

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: Related CAS# CAS# 111974-72-2 ( Quetiapine hemifumarate) CAS#111974-69-7 ( Quetiapine free base).

Product Data:
Product Data
Instruction:
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Biological target: Quetiapine hemifumarate is a dopamine receptor antagonist with a pIC50 of 6.33 for human D2 receptor. It has moderate to high affinity for the human D2, HT1A, 5-HT2A, 5-HT2C receptor with pKis of 7.25, 5.74, 7.54, 5.55.
In vitro activity: Using PC12 cell cultures and the MTT assay for cell viability found that the atypical antipsychotics clozapine, quetiapine, and risperidone may exert a neuroprotective function after serum withdrawal through the modulation of SOD1 and p75NTR expression. They also found that 1) the atypical antipsychotics (clozapine, quetiapine, and risperidone) can protect PC12 cells from death after serum withdrawal and 2) these drugs up-regulated the SOD1 gene expression to more than 120% and also down-regulated p75NTR mRNA levels to less than 65% of their respective control values. Reference: J Neurosci Res. 2002 Jul 15;69(2):278-83. https://pubmed.ncbi.nlm.nih.gov/12111809/
In vivo activity: Quetiapine significantly reduced depressive-like behaviors induced by chronic mild stress in adult rats. MPO activity and IL-6 levels increased in the serum of animals submitted to CMS. Quetiapine significantly reduced MPO activity and IL-6 levels. These results corroborate other evidence, indicating that chronic stress is a relevant phenomenon in the etiology of depression and suggesting that quetiapine induces an antidepressant effect because it reduces oxidative and inflammatory mechanisms. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2023 Feb 3. https://pubmed.ncbi.nlm.nih.gov/36735044/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 22.1 50.00

Preparing Stock Solutions

The following data is based on the product molecular weight 441.54 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. Bai O, Wei Z, Lu W, Bowen R, Keegan D, Li XM. Protective effects of atypical antipsychotic drugs on PC12 cells after serum withdrawal. J Neurosci Res. 2002 Jul 15;69(2):278-83. doi: 10.1002/jnr.10290. PMID: 12111809. 2. Gahr M, Kölle MA, Freudenmann RW, Schönfeldt-Lecuona C. Aseptic gingivitis related to quetiapine hemifumarate. Pharmacopsychiatry. 2013 Jan;46(1):39-40. doi: 10.1055/s-0032-1321906. Epub 2012 Aug 22. PMID: 22915485. 3. Cross AJ, Widzowski D, Maciag C, Zacco A, Hudzik T, Liu J, Nyberg S, Wood MW. Quetiapine and its metabolite norquetiapine: translation from in vitro pharmacology to in vivo efficacy in rodent models. Br J Pharmacol. 2016 Jan;173(1):155-66. doi: 10.1111/bph.13346. Epub 2015 Dec 1. PMID: 26436896; PMCID: PMC4813385.
In vitro protocol: 1. Bai O, Wei Z, Lu W, Bowen R, Keegan D, Li XM. Protective effects of atypical antipsychotic drugs on PC12 cells after serum withdrawal. J Neurosci Res. 2002 Jul 15;69(2):278-83. doi: 10.1002/jnr.10290. PMID: 12111809.
In vivo protocol: 1. Gahr M, Kölle MA, Freudenmann RW, Schönfeldt-Lecuona C. Aseptic gingivitis related to quetiapine hemifumarate. Pharmacopsychiatry. 2013 Jan;46(1):39-40. doi: 10.1055/s-0032-1321906. Epub 2012 Aug 22. PMID: 22915485. 2. Cross AJ, Widzowski D, Maciag C, Zacco A, Hudzik T, Liu J, Nyberg S, Wood MW. Quetiapine and its metabolite norquetiapine: translation from in vitro pharmacology to in vivo efficacy in rodent models. Br J Pharmacol. 2016 Jan;173(1):155-66. doi: 10.1111/bph.13346. Epub 2015 Dec 1. PMID: 26436896; PMCID: PMC4813385.

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1: Gonçalves de Lima L, Rossi de Campos D. Development of a level A in vitro-in
vivo correlation for extended release dosage forms of quetiapine fumarate. Drug
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2: Upadhyay P, Trivedi J, Pundarikakshudu K, Sheth N. Comparative study between
simple and optimized liposomal dispersion of quetiapine fumarate for diffusion
through nasal route. Drug Deliv. 2015 Dec 8:1-8. [Epub ahead of print] PubMed
PMID: 26643946.


3: Kalyankar P, Panzade P, Lahoti S. Formulation Design and Optimization of
Orodispersible Tablets of Quetiapine Fumarate by Sublimation Method. Indian J
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PMCID: PMC4502140.


4: Bauer M, Thase ME, Liu S, Earley W, Eriksson H. Analysis of potentially
predictive factors of efficacy of adjunct extended-release quetiapine fumarate in
patients with major depressive disorder. J Psychopharmacol. 2015
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25257148.


5: Kulinowski P, Woyna-Orlewicz K, Rappen GM, Haznar-Garbacz D, Węglarz WP,
Dorożyński PP. An understanding of modified release matrix tablets behavior
during drug dissolution as the key for prediction of pharmaceutical product
performance - case study of multimodal characterization of quetiapine fumarate
tablets. Int J Pharm. 2015 Apr 30;484(1-2):235-45. doi:
10.1016/j.ijpharm.2015.02.040. Epub 2015 Feb 18. PubMed PMID: 25701626.


6: Li JC, Zhang WJ, Zhu JX, Zhu N, Zhang HM, Wang X, Zhang J, Wang QQ.
Preparation and brain delivery of nasal solid lipid nanoparticles of quetiapine
fumarate in situ gel in rat model of schizophrenia. Int J Clin Exp Med. 2015 Oct
15;8(10):17590-600. eCollection 2015. PubMed PMID: 26770349; PubMed Central
PMCID: PMC4694249.


7: Bonafede M, Locklear JC, Wahlqvist P, Fajutrao L, Szamosi J, Pan K, Eriksson
H. Impact of once-daily extended-release quetiapine fumarate on hospitalization
length in patients with acute bipolar mania. J Comp Eff Res. 2015 Jan;4(1):51-9.
doi: 10.2217/cer.14.48. PubMed PMID: 25168473.


8: Kasper S, Montagnani G, Trespi G, Di Fiorino M. Treatment of depressive
symptoms in patients with schizophrenia: a randomized, open-label,
parallel-group, flexible-dose subgroup analysis of patients treated with
extended-release quetiapine fumarate or risperidone. Int Clin Psychopharmacol.
2015 Jan;30(1):14-22. doi: 10.1097/YIC.0000000000000053. PubMed PMID: 25356632.


9: Montgomery SA, Locklear JC, Svedsäter H, Eriksson H. Efficacy of once-daily
extended release quetiapine fumarate in patients with different levels of
severity of generalized anxiety disorder. Int Clin Psychopharmacol. 2014
Sep;29(5):252-62. doi: 10.1097/YIC.0000000000000026. PubMed PMID: 24394383.


10: Locklear JC, Wahlqvist P, Gustafsson U, Udd M, Fajutrao L, Eriksson H. Impact
of extended-release quetiapine fumarate on hospitalization length and cost in
schizophrenia and bipolar disorder patients: a retrospective, hospital-based,
US-cohort analysis. J Comp Eff Res. 2014 Jul;3(4):335-44. doi: 10.2217/cer.14.27.
PubMed PMID: 25275231.


11: Findling RL, Pathak S, Earley WR, Liu S, DelBello MP. Efficacy and safety of
extended-release quetiapine fumarate in youth with bipolar depression: an 8 week,
double-blind, placebo-controlled trial. J Child Adolesc Psychopharmacol. 2014
Aug;24(6):325-35. doi: 10.1089/cap.2013.0105. Epub 2014 Jun 23. PubMed PMID:
24956042; PubMed Central PMCID: PMC4137347.


12: Li Q, Su YA, Liu Y, Chen JX, Tan YL, Yang FD, Si TM. Pharmacokinetics and
tolerability of extended-release quetiapine fumarate in Han Chinese patients with
schizophrenia. Clin Pharmacokinet. 2014 May;53(5):455-65. doi:
10.1007/s40262-013-0127-9. PubMed PMID: 24385309.


13: Weisler R, Montgomery SA, Earley WR, Szamosi J, Eriksson H. Extended release
quetiapine fumarate in patients with major depressive disorder: suicidality data
from acute and maintenance studies. J Clin Psychiatry. 2014 May;75(5):520-7. doi:
10.4088/JCP.13m08624. PubMed PMID: 24816198.


14: Di Fiorino M, Montagnani G, Trespi G, Kasper S. Extended-release quetiapine
fumarate (quetiapine XR) versus risperidone in the treatment of depressive
symptoms in patients with schizoaffective disorder or schizophrenia: a
randomized, open-label, parallel-group, flexible-dose study. Int Clin
Psychopharmacol. 2014 May;29(3):166-76. doi: 10.1097/YIC.0000000000000017. PubMed
PMID: 24681810.


15: Montgomery SA, Altamura AC, Katila H, Datto C, Szamosi J, Eriksson H.
Efficacy of extended release quetiapine fumarate monotherapy in elderly patients
with major depressive disorder: secondary analyses in subgroups of patients
according to baseline anxiety, sleep disturbance, and pain levels. Int Clin
Psychopharmacol. 2014 Mar;29(2):93-105. doi: 10.1097/YIC.0000000000000007. PubMed
PMID: 24162081.


16: Clayton AH, Locklear JC, Svedsäter H, McIntyre RS. Sexual functioning in
patients with major depressive disorder in randomized placebo-controlled studies
of extended release quetiapine fumarate. CNS Spectr. 2014 Apr;19(2):182-96. doi:
10.1017/S1092852913000631. Epub 2013 Sep 25. PubMed PMID: 24067192.


17: McIntyre A, Paisley D, Kouassi E, Gendron A. Quetiapine fumarate
extended-release for the treatment of major depression with comorbid fibromyalgia
syndrome: a double-blind, randomized, placebo-controlled study. Arthritis
Rheumatol. 2014 Feb;66(2):451-61. doi: 10.1002/art.38228. PubMed PMID: 24504819.


18: Wang G, McIntyre A, Earley WR, Raines SR, Eriksson H. A randomized,
double-blind study of the efficacy and tolerability of extended-release
quetiapine fumarate (quetiapine XR) monotherapy in patients with major depressive
disorder. Neuropsychiatr Dis Treat. 2014 Jan 30;10:201-16. doi:
10.2147/NDT.S50248. eCollection 2014. PubMed PMID: 24511235; PubMed Central
PMCID: PMC3916085.


19: Khan A, Atkinson S, Mezhebovsky I, She F, Leathers T, Pathak S.
Extended-release quetiapine fumarate (quetiapine XR) as adjunctive therapy in
patients with generalized anxiety disorder and a history of inadequate treatment
response: a randomized, double-blind study. Ann Clin Psychiatry. 2014
Feb;26(1):3-18. PubMed PMID: 24660224.


20: Bandelow B, Bauer M, Vieta E, El-Khalili N, Gustafsson U, Earley WR, Eriksson
H. Extended release quetiapine fumarate as adjunct to antidepressant therapy in
patients with major depressive disorder: pooled analyses of data in patients with
anxious depression versus low levels of anxiety at baseline. World J Biol
Psychiatry. 2014 Feb;15(2):155-66. doi: 10.3109/15622975.2013.842654. PubMed
PMID: 24506289.