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Quetiapine
Quetiapine
Synonyms ICI-204636, ZD-5077, ZM-204636
Brand names Seroquel
IUPAC name

IUPAC name
2-(2-[4-(dibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy)ethanol
ChemSpider

4827

DrugBank

DB01224

PubChem

5002

PDB fields

N/A

Formula

C21H25N3O2S

InChI
InChI
1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2
InChIKey
InChIKey
URKOMYMAXPYINW-UHFFFAOYSA-N
SMILES
SMILES
C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42
(Jmol 3D structure)
Mol. mass

383.5071 g/mol

Quetiapine is an atypical antipsychotic that is used in the treatment of schizophrenia, bipolar disorder (including for manic and depressive phases and maintenance treatments to prevent future mood episodes), Parkinson's disease psychosis and as an adjunct (add-on medication) in treatment-resistant cases of major depression.[1] Recently it has been suggested that it might be of benefit in multiple sclerosis, although this theory is yet to be confirmed in clinical trials.[2]


Unexpectedly, however, as it does not generate euphoria it has been subject to misuse and abuse.[3][4][5]

Side effectsEdit

It causes less weight gain and changes in blood sugar and metabolic parameters than clozapine (although statistical significance has not been reached), iloperidone, olanzapine and zotepine, although more than amisulpride, aripiprazole, asenapine, haloperidol, lurasidone and ziprasidone.[6] It produces virtually no movement disorders and prolactin elevation as it is a quick on-off D2 antagonist due to its very low affinity for this receptor.[6]

PropertiesEdit

It has a short half-life of 6-7 hours, although it has an active metabolite called norquetiapine (N-desalkylquetiapine), hence permitting twice daily administration for immediate release formulations.[1] An extended release (XR) formulation is available that permits for once daily administration (although it is rather expensive at >$1 per tablet from the Chemist Warehouse, when it is not covered by the PBS). Norquetiapine is a significantly more potent partial agonist at 5-HT1A receptors, antagonist at α2 adrenergic, 5-HT2C and 5-HT7 receptors and noradrenaline reuptake inhibitor.[7]

Norquetiapine

Norquetiapine's structure



External linksEdit

Reference listEdit

  1. 1.0 1.1 Brayfield, A, ed. (13 August 2013). "Quetiapine Fumarate". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 7 September 2014. 
  2. Zhornitsky, S; Wee Yong, V; Koch, MW; Mackie, A; Potvin, S; Patten, SB; Metz, LM (October 2013). "Quetiapine fumarate for the treatment of multiple sclerosis: focus on myelin repair.". CNS Neuroscience & Therapeutics 19 (10): 737–44. PMID 23870612. doi:10.1111/cns.12154. 
  3. Tcheremissine, OV (November 2008). "Is quetiapine a drug of abuse? Reexamining the issue of addiction.". Expert Opinion on Drug Safety 7 (6): 739–48. PMID 18983220. doi:10.1517/14740330802496883. 
  4. Fischer, BA; Boggs, DL (March 2010). "The role of antihistaminic effects in the misuse of quetiapine: a case report and review of the literature.". Neuroscience and Biobehavioral Reviews 34 (4): 555–8. PMID 19896973. doi:10.1016/j.neubiorev.2009.11.003. 
  5. Dobbin, Malcolm (June 2014). "Pharmaceutical drug misuse in Australia". Australian Prescriber 37 (3): 79–81. 
  6. 6.0 6.1 Leucht, S; Cipriani, A; Spineli, L; Mavridis, D; Orey, D; Richter, F; Samara, M; Barbui, C; Engel, RR; Geddes, JR; Kissling, W; Stapf, MP; Lässig, B; Salanti, G; Davis, JM (September 2013). "Comparative efficacy and tolerability of 15 antipsychotic drugs in schizophrenia: a multiple-treatments meta-analysis.". Lancet 382 (9896): 951–62. PMID 23810019. doi:10.1016/S0140-6736(13)60733-3. 
  7. López-Muñoz, F; Alamo, C (September 2013). "Active metabolites as antidepressant drugs: the role of norquetiapine in the mechanism of action of quetiapine in the treatment of mood disorders.". Frontiers in Psychiatry 4: 102. PMC 3770982. PMID 24062697. doi:10.3389/fpsyt.2013.00102. 

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