Tìm theo
Escitalopram
Các tên gọi khác (7 ) :
  • (+)-Citalopram
  • (S)-Citalopram
  • Escitalopram Oxalate
  • Escitalopramum
  • Esertia
  • S-(+)-Citalopram
  • S(+)-Citalopram
antidepressive agents second generation, serotonin uptake inhibitors
Thuốc Gốc
Small Molecule
CAS: 128196-01-0
ĐG : AQ Pharmaceuticals Inc. , http://www.aqpharmaceuticals.com
CTHH: C20H21FN2O
PTK: 324.3919
Escitalopram, the S-enantiomer of citalopram, belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Escitalopram may be used to treat major depressive disorder (MDD) and generalized anxiety disorder (GAD).
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C20H21FN2O
Phân tử khối
324.3919
Monoisotopic mass
324.163791509
InChI
InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1
InChI Key
InChIKey=WSEQXVZVJXJVFP-FQEVSTJZSA-N
IUPAC Name
(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional IUPAC Name
escitalopram
SMILES
CN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Độ hòa tan
5.88e-03 g/l
logP
3.5
logS
-4.7
pKa (Strongest Basic)
9.78
PSA
36.26 Å2
Refractivity
94.02 m3·mol-1
Polarizability
35.21 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
3
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Escitalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that escitalopram is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Escitalopram has no significant affinity for adrenergic (alpha1, alpha2, beta), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of escitalopram was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Escitalopram does not inhibit monoamine oxidase.
Cơ Chế Tác Dụng : Escitalopram, the S-enantiomer of citalopram, belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Escitalopram may be used to treat major depressive disorder (MDD) and generalized anxiety disorder (GAD). The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Escitalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
Dược Động Học :
▧ Absorption :
The absolute bioavailability of citalopram is about 80% relative to an intravenous dose.
▧ Volume of Distribution :
* 12 L/kg
▧ Protein binding :
~56%
▧ Metabolism :
Mainly hepatic. Escitalopram undergoes N-demethylation to S-demethylcitalopram (S-DCT) and S-didemethylcitalopram (S-DDCT). CYP3A4 and CYP2C19 are the enzymes responsible for this N-demethylation reaction.
▧ Route of Elimination :
Following oral administrations of escitalopram, the fraction of drug recovered in the urine as escitalopram and S-demethylcitalopram (S-DCT) is about 8% and 10%, respectively. The oral clearance of escitalopram is 600 mL/min, with approximately 7% of that due to renal clearance. Escitalopram is metabolized to S-DCT and S-didemethylcitalopram (S-DDCT).
▧ Half Life :
27-32 hours
▧ Clearance :
* oral cl=600 mL/min [Following oral administrations]
Độc Tính : Signs of overdose include convulsions, coma, dizziness, hypotension, insomnia, nausea, vomiting, sinus tachycardia, somnolence, and ECG changes (including QT prolongation).
Chỉ Định : Labeled indications include major depressive disorder (MDD) and generalized anxiety disorder (GAD). Unlabeled indications include treatment of mild dementia-associated agitation in nonpsychotic patients.
Tương Tác Thuốc :
  • Almotriptan Increased risk of CNS adverse effects
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Carvedilol The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Eletriptan Increased risk of CNS adverse effects
  • Frovatriptan Increased risk of CNS adverse effects
  • Ginkgo biloba Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
  • Isocarboxazid Possible severe adverse reaction with this combination
  • Ketoprofen Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
  • Linezolid Combination associated with possible serotoninergic syndrome
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Metoprolol The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
  • Naratriptan Increased risk of CNS adverse effects
  • Oxycodone Increased risk of serotonin syndrome
  • Phenelzine Possible severe adverse reaction with this combination
  • Pimozide The SSRI, escitalopram, increases the effect and toxicity of pimozide.
  • Propranolol The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
  • Rasagiline Possible severe adverse reaction with this combination
  • Rizatriptan Increased risk of CNS adverse effects
  • Selegiline Possible severe adverse reaction with this combination
  • Sibutramine Risk of serotoninergic syndrome
  • St. John's Wort St. John's Wort increases the effect and toxicity of the SSRI, escitalopram.
  • Sumatriptan Increased risk of CNS adverse effects
  • Telaprevir Telaprevir decreases Cmax, Cmin, and AUC of escitalopram however the mechanism of this interaction is unknown. Concomitant therapy may call for dose adjustment.
  • Telithromycin Telithromycin may reduce clearance of Escitalopram. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Escitalopram if Telithromycin is initiated, discontinued or dose changed.
  • Tiaprofenic acid Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
  • Ticlopidine Ticlopidine may decrease the metabolism and clearance of Escitalopram. Consider alternate therapy or monitor for adverse/toxic effects of Ambrisentan if Escitalopram is initiated, discontinued or dose changed.
  • Tolmetin Increased antiplatelet effects may enhance the risk of bleeding. Alternate therapy may be considered or monitor for inreased bleeding during concomitant therapy.
  • Tramadol Tramadol may increase the risk of serotonin syndrome and seizures.
  • Tranylcypromine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
  • Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Treprostinil The prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Escitalopram. Monitor for increased bleeding during concomitant thearpy.
  • Trimipramine The SSRI, Escitalopram, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Escitalopram is initiated, discontinued or dose changed.
  • Triprolidine The CNS depressants, Triprolidine and Escitalopram, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
  • Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of escitalopram by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of escitalopram if voriconazole is initiated, discontinued or dose changed.
  • Ziprasidone Additive QTc-prolongation may occur increasing the risk of life-threatening ventricular arrhythmias and torsade de pointes. Concomitant therapy should be avoided.
  • Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and escitalopram, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
  • Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Liều Lượng & Cách Dùng : Solution - Oral - 5 mg/5 ml
Tablet, film coated - Oral - 10 mg
Tablet, film coated - Oral - 20 mg
Tablet, film coated - Oral - 5 mg
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Lexapro 5 mg tablet
    Giá bán buôn : USD >3.4
    Đơn vị tính : tablet
  • Biệt dược thương mại : Lexapro 10 mg tablet
    Giá bán buôn : USD >3.55
    Đơn vị tính : tablet
  • Biệt dược thương mại : Lexapro 20 mg tablet
    Giá bán buôn : USD >3.71
    Đơn vị tính : tablet
  • Biệt dược thương mại : Lexapro 5 mg/5ml Solution
    Giá bán buôn : USD >0.72
    Đơn vị tính : ml
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Cipralex
  • Công ty : Forest
    Sản phẩm biệt dược : Lexapro
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01175
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=146570
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507040
ChemSpider
http://www.chemspider.com/Chemical-Structure.129277.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0456-2005-01
PharmGKB
http://www.pharmgkb.org/drug/PA10074
Wikipedia
http://en.wikipedia.org/wiki/Escitalopram
RxList
http://www.rxlist.com/cgi/generic/lexapro.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/lex1642.shtml
Drugs.com
http://www.drugs.com/cdi/escitalopram.html
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