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Quetiapine(CAS No. 111974-69-7)

Quetiapine C21H25N3O2S (cas 111974-69-7) Molecular Structure

111974-69-7 Structure

Identification and Related Records

【Name】
Quetiapine
【CAS Registry number】
111974-69-7
【Synonyms】
2-(2-(4-Dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)ethanol
Co-Quetiapine
Seroquel
Ethanol,2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-
【Molecular Formula】
C21H25N3O2S (Products with the same molecular formula)
【Molecular Weight】
383.5071
【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】
URKOMYMAXPYINW-UHFFFAOYSA-N
【Canonical SMILES】
C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42
【MOL File】
111974-69-7.mol

Chemical and Physical Properties

【Appearance】
white to off-white crystalline powder
【Density】
1.27 g/cm3
【Melting Point】
172 - 174 C
【Boiling Point】
556.5 °C at 760 mmHg
【Vapour】
3.22E-13mmHg at 25°C
【Flash Point】
290.4 °C
【Water】
Soluble
【Solubilities】
Soluble Appearance:white to off-white crystalline powder
Transport Information:HAZARD
Hazard Symbols:UN NO.
【Color/Form】
Solid
【Computed Properties】
Molecular Weight:383.5071 [g/mol]
Molecular Formula:C21H25N3O2S
XLogP3-AA:2.1
H-Bond Donor:1
H-Bond Acceptor:5
Rotatable Bond Count:6
Exact Mass:383.166748
MonoIsotopic Mass:383.166748
Topological Polar Surface Area:73.6
Heavy Atom Count:27
Formal Charge:0
Complexity:496
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Cation Count:2
Feature 3D Ring Count:4
Effective Rotor Count:7.4
Conformer Sampling RMSD:0.8
CID Conformer Count:119

Safety and Handling

【Hazard Codes】
UN NO.
【Transport】
HAZARD
【Formulations/Preparations】
/Oral formulations/: Tablets, film-coated, 25 mg, 100 mg, 200 mg, 300 mg (of quetiapine) Seroquel with povidone, (AstraZeneca)
Trade name: Seroquel
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl quetiapine fumarate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Quetiapine fumarate/
【Octanol/Water Partition Coefficient】
log Kow = 2.29
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: EJ Warawa, BM Migler, EP 240228; eidem, US 4879288 (1987, 1989 both to ICI).

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
【Biomedical Effects and Toxicity】
Quetiapine fumarate is rapidly absorbed after oral administration, reaching peak plasma concentrations in 1.5 hours. The tablet formulation is 100% bioavailable relative to solution. The bioavailability of quetiapine is marginally affected by administration with food, with Cmax and AUC values increased by 25% and 15%, respectively.
Steady state concentrations are expected to be achieved within two days of dosing.
Quetiapine is widely distributed throughout the body with an apparent volume of distribution of 10 +/-4 L/kg. It is 83% bound to plasma proteins at therapeutic concentrations.
Hepatically impaired patients (n=8) had a 30% lower mean oral clearance of quetiapine than normal subjects. In two of the 8 hepatically impaired patients, AUC and C max were 3-times higher than those observed typically in healthy subjects. Since quetiapine is extensively metabolized by the liver, higher plasma levels are expected in the hepatically impaired population...
Quetiapine is distributed into milk in animals. Not known whether quetiapine is distributed into milk in humans.
A 26-year-old mother and her 3-month-old son were studied over a 24 hour quetiapine dose interval at steady-state. Quetiapine concentrations were quantified by high-performance liquid chromatography. Infant exposure was calculated as the concentration in milk multiplied by an estimated milk production of 0.15 L/kg/day and normalized to the weight-adjusted maternal dose. The average concentration in milk was 41 ug/L, the M:P ratio (measured using average concentrations in the elimination phase) was 0.29, and the relative infant dose was 0.09% of the maternal weight-adjusted dose (7273 ug/kg/day). The infant plasma concentration of 1.4 ug/L was some 6% of the corresponding maternal plasma concentration. No adverse effects were noted in the infant. [Rampono J, Kristensen J et al; Ann Pharmacother 41 (4): 711-4 (2007)] PubMed Abstract
The aim of this study was to study the placental transfer of quetiapine, a widely used atypical antipsychotic, with special reference to the role of the placental transporter protein, P-glycoprotein (P-gp). This was performed in 18 dually perfused placentas, using the well established P-gp inhibitors PSC833 (valspodar) and GG918 to inhibit the function of P-gp. We also aimed to clarify the significance of two potentially functional ABCB1 single nuclear polymorphisms (SNPs), 2677G>T/A and 3435C>T, on the transplacental transfer (TPT) of quetiapine. The placental transfer of quetiapine in the control group as measured by TPT(AUC) % (absolute fraction of the dose crossing placenta) was 3.7%, which is 29% less than the transfer of the freely diffusible antipyrine, which was 5.2%. The P-gp inhibitors had no significant effect on the transfer of quetiapine as measured by TPT(AUC) % (P = 0.77). No correlation was found between the transplacental transfer of quetiapine (TPT(AUC) %) and placental P-gp expression (P = 0.61). The 3435T allele in exon 26 was associated with significantly higher placental transfer of quetiapine (P = 0.04). /Investigators/ conclude that quetiapine passes the human placenta but that the blood-placental barrier partially limits the transplacental transfer of quetiapine. [Rahi M, Heikkinen T et al; J Psychopharmacol 21 (7): 751-6 (2007)] PubMed Abstract
Following oral administration of a single dose of quetiapine, approximately 73 and 20% of the dose is excreted in urine and feces, respectively; less than 1% of the dose is excreted unchanged.

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