(2E)-but-2-enedioic acid; 2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol; 2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol

• ChemBase ID: 72798
• Molecular Formular: C46H54N6O8S2
• Molecular Mass: 883.08636
• Monoisotopic Mass: 882.34445472
• SMILES: c1ccc2c(c1)N=C(c1c(S2)cccc1)N1CCN(CC1)CCOCCO.OC(=O)/C=C/C(=O)O.c12c(cccc1)N=C(c1c(S2)cccc1)N1CCN(CC1)CCOCCO
• Canonical SMILES: OC(=O)/C=C/C(=O)O.OCCOCCN1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2.OCCOCCN1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2
• InChI: 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+
• InChIKey: ZTHJULTYCAQOIJ-WXXKFALUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; 2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol; 2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol; bis(2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,9,11,13-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol); but-2-enedioic acid; (2E)-but-2-enedioic acid; bis(2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol)
• IUPAC Traditional name: 2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethanol; fumaric acid; quetiapine; butenedioic acid; bis(quetiapine); (2E)-but-2-enedioic acid; bis(2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol); fumaric acid; bis(quetiapine)
• Synonyms: ICI-204636; ZD 5077; ZM 204636; Quetiapine fumarate; 2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol hemifumarate; Quetiapine fumarate; Quetiapine hemifumarate salt; Seroquel; Ketipinor; Quetiapine Fumarate; 2-(2-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy)ethanol hemifumarate

Database IDs

• CAS Number: 111974-72-2
• MDL Number: MFCD03423782
• PubChem SID: 162037719
• PubChem CID: 5281025

CALCULATED PROPERTIES

• Acid pKa: 15.121227
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.2358336
• LogD (pH = 7.4): 2.6430545
• Log P: 2.8079426
• Molar Refractivity: 114.0854 cm^3
• Polarizability: 42.748154 Å^3
• Polar Surface Area: 48.3 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: -20°C; desiccated
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Antagonist of dopamine and serotonin receptors; Specifically the D1 and D2 dopamine, the alpha 1 adrenoreceptor and alpha 2 adrenoreceptor, and 5-HT1A and 5-HT2 serotonin receptor

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: 0.5 Fumarate; Fumarate
• Application(s): Antipsychotic and neuroleptic agent
• Empirical Formula (Hill Notation): C21H25N3O2S · 0.5C4H4O4

DETAILS

Selleck Chemicals - S1763

Research Area: Neurological Disease
Biological Activity:
Quetiapine fumarate(Seroquel) is an atypical antipsychotic used in the treatment of schizophrenia, bipolar I mania, bipolar II depression, bipolar I depression, and used off-label for a variety of other purposes, including insomnia and anxiety disorders.This means Quetiapine is dopamine, serotonin and adrenergic antagonist, anticholinergic substance and antihistamine. [1]

Sigma Aldrich - Q3638

Biochem/physiol Actions
Quetiapine hemifumarate is an atypical antipsychotic, a combined serotonin (5HT2) and dopamine (D2) receptor antagonist.

REFERENCES

• http://en.wikipedia.org/wiki/Quetiapine
• Eur. Pat., 1987, ICI Americas, 240 228; CA, 108, 37876q, (synth, pharmacol)
• Campbell, A. et al., Psychopharmacology (Berlin), 1991, 103, 323, (pharmacol)
• Pullen, R.H. et al., J. Chromatogr., 1992, 573, 49, (hplc, gc-ms)
• Saller, C.F. et al., Psychopharmacology (Berlin), 1993, 112, 285; 293; 299, (pharmacol)
• Goldstein, J.M., Drugs of Today (Barcelona), 1999, 35, 193-210
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 690
• Warawa, E.J. et al., J. Med. Chem., 2001, 44, 372-389, (synth, pharmacol)