Tìm theo
Citalopram
Các tên gọi khác (2) :
  • Citadur
  • Nitalapram
Thuốc điều trị về tâm thần
Thuốc Gốc
Small Molecule
CAS: 59729-33-8
ATC: N06AB04, N06AB10
ĐG : Actavis Group , http://www.actavis.com
CTHH: C20H21FN2O
PTK: 324.3919
Citalopram hydrobromide belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Citalopram and its N-demethylated metabolites exist as a racemic mixture but its effects are largely due to the S-enantiomer, S-citalopram and S-demthylcitalopram. 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. Citalopram is approved for treatment of depression. Unlabeled indications include mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy. Citalopram has the fewest drug-drug interactions of the SSRIs.
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
InChI Key
InChIKey=WSEQXVZVJXJVFP-UHFFFAOYSA-N
IUPAC Name
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional IUPAC Name
citalopram
SMILES
CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Độ tan chảy
182-183 °C
Độ hòa tan
Sparingly soluble
logP
3.5
logS
-4.7
pKa (Strongest Basic)
9.78
PSA
36.26 Å2
Refractivity
94.02 m3·mol-1
Polarizability
35.4 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 : Citalopram 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 citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that citalopram is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Citalopram has no significant affinity for adrenergic (α1, α2, β), 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 citalopram was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase.
Cơ Chế Tác Dụng : Citalopram hydrobromide belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Citalopram and its N-demethylated metabolites exist as a racemic mixture but its effects are largely due to the S-enantiomer, S-citalopram and S-demthylcitalopram. 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. Citalopram is approved for treatment of depression. Unlabeled indications include mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy. Citalopram has the fewest drug-drug interactions of the SSRIs. The antidepressant, antiobsessive-compulsive, and antibulimic actions of citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Citalopram 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 :
Rapidly and well absorbed from the GI tract. Peak plasma concentrations occur within 4 hours of a single orally administered dose. Bioavailability is 80% following oral administration. Food does not affect absorption.
▧ Volume of Distribution :
* 12 L/kg Citalopram is highly lipophilic and likely widely distributed throughout the body, including the blood-brain-barrier. However, its metabolite, demethylcitalopram does not cross the barrier well.
▧ Protein binding :
Citalopram, dimethylcitalopram, and didemethylcitalopram is 80% bound to plasma proteins.
▧ Metabolism :
Citalopram is metabolized mainly in the liver via N-demethylation to its principle metabolite, demethylcitalopram. Other metabolites include didemethylcitalopram, citalopram N-oxide, and a deaminated propionic acid derivative. However, the predominant entity in plasma is unchanged citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be principally involved in producing demethylcitalopram. Demethylcitalopram appears to be further N-demethylated by CYP2D6 to didemethylcitalopram. Citalopram metabolites possess little pharmacologic activity in comparison to their parent compound and do not likely contribute to the clinical effect of the drug.
▧ Route of Elimination :
12-23% of an oral dose of citalopram is recovered unchanged in the urine, while 10% of the dose is recovered in the feces.
▧ Half Life :
35 hours
▧ Clearance :
The systemic clearance of citalopram was 330 mL/min, with approximately 20% of that due to renal clearance.
Độc Tính : Symptoms most often accompanying citalopram overdose, alone or in combination with other drugs and/or alcohol, included dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. In more rare cases, observed symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and very rare cases of torsade de pointes). Acute renal failure has been very rarely reported accompanying overdose. Withdrawal symptoms include flu-like symptoms, insomnia, nausea, imbalance, sensory changes and hyperactivity.
Chỉ Định : For the treatment of depression. Unlabeled indications include: treatment of mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy.
Tương Tác Thuốc :
  • Acenocoumarol The SSRI, citalopram, increases the effect of anticoagulant, acenocoumarol.
  • Almotriptan Increased risk of CNS adverse effects
  • Anisindione The SSRI, citalopram, increases the effect of anticoagulant, anisindione.
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Carvedilol The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
  • Clarithromycin Possible serotoninergic syndrome with this combination
  • Clozapine The antidepressant increases the effect of clozapine
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Dicoumarol The SSRI, citalopram, increases the effect of anticoagulant, dicumarol.
  • Eletriptan Increased risk of CNS adverse effects
  • Erythromycin Possible serotoninergic syndrome with this combination
  • Etravirine Citalopram, when used concomitantly with etravirine (a CYP2C19 inhibitor), may experience an increase in serum concentration. It is recommended to maintain the dose of citalopram below 20mg/day, and to monitor for toxicity. The symptoms which often accompany citalopram overdose are dizziness, sweating, nausea, vomiting, tremor, somnolence,sinus tachycardia,amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, acute renal failure, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and torsade de pointes).
  • 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
  • Josamycin Possible serotoninergic sydrome 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, citalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
  • Moclobemide Possible serotoninergic syndrome
  • Naratriptan Increased risk of CNS adverse effects
  • Oxycodone Increased risk of serotonin syndrome
  • Phenelzine Possible severe adverse reaction with this combination
  • Pimozide The SSRI, citalopram, may increase the effect and toxicity of pimozide.
  • Propranolol The SSRI, citalopram, 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, citalopram.
  • Sumatriptan Increased risk of CNS adverse effects
  • Telithromycin Telithromycin may reduce clearance of Citalopram. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Citalopram 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 Citalopram. Consider alternate therapy or monitor for adverse/toxic effects of Citalopram if Ticlopidine 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 The use of two serotonin modulators, such as citalopram and tramadol, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
  • 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, Citalopram. Monitor for increased bleeding during concomitant thearpy.
  • Trimipramine The SSRI, Citalopram, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Citalopram is initiated, discontinued or dose changed.
  • Triprolidine The CNS depressants, Triprolidine and Citalopram, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
  • Troleandomycin Possible serotoninergic syndrome with this combination
  • Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of citalopram by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of citalopram if voriconazole is initiated, discontinued or dose changed.
  • Warfarin The SSRI, citalopram, increases the effect of anticoagulant, warfarin.
  • Ziprasidone Additive QTc-prolongation may occur increasing the risk of life-threatening ventricular arrhythmias and torsade de pointes. Concomitant therapy should be avoided.
  • Zolmitriptan The use of two serotonin modulators, such as zolmitriptan and citalopram, 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 - 10 mg/5 ml
Tablet - Oral - 10 mg, 20 mg, 40 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Akarin
  • Công ty :
    Sản phẩm biệt dược : Celapram
  • Sản phẩm biệt dược : Celexa
  • Công ty :
    Sản phẩm biệt dược : Ciazil
  • Công ty :
    Sản phẩm biệt dược : Cilift
  • Công ty :
    Sản phẩm biệt dược : Cipram
  • Công ty :
    Sản phẩm biệt dược : Cipramil
  • Công ty :
    Sản phẩm biệt dược : Ciprapine
  • Công ty :
    Sản phẩm biệt dược : Citabax
  • Công ty :
    Sản phẩm biệt dược : Citalec
  • Công ty :
    Sản phẩm biệt dược : Citol
  • Công ty :
    Sản phẩm biệt dược : Citopam
  • Công ty :
    Sản phẩm biệt dược : Citox
  • Công ty :
    Sản phẩm biệt dược : Citrol
  • Công ty :
    Sản phẩm biệt dược : Dalsan
  • Công ty :
    Sản phẩm biệt dược : Elopram
  • Công ty :
    Sản phẩm biệt dược : Humorup
  • Công ty :
    Sản phẩm biệt dược : Oropram
  • Công ty :
    Sản phẩm biệt dược : Pramcit
  • Công ty :
    Sản phẩm biệt dược : Recital
  • Công ty :
    Sản phẩm biệt dược : Seropram
  • Công ty :
    Sản phẩm biệt dược : Talam
  • Công ty :
    Sản phẩm biệt dược : Talohexal
  • Công ty :
    Sản phẩm biệt dược : Temperax
  • Công ty :
    Sản phẩm biệt dược : Vodelax
  • Công ty :
    Sản phẩm biệt dược : Zentius
  • Công ty :
    Sản phẩm biệt dược : Zetalo
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00215
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2771
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508746
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07572
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D07704
ChemSpider
http://www.chemspider.com/Chemical-Structure.2669.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=25870
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-6231-01
PharmGKB
http://www.pharmgkb.org/drug/PA449015
Wikipedia
http://en.wikipedia.org/wiki/Citalopram
RxList
http://www.rxlist.com/cgi/generic/citalo.htm
Drugs.com
http://www.drugs.com/citalopram.html
... loading
... loading