Tìm theo
Sertraline
Các tên gọi khác (8 ) :
  • (+)-Sertraline
  • (1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine
  • (1S,4S)-Sertraline
  • cis-(+)-Sertraline
  • CP 51974
  • Sertralina
  • Sertraline
  • Sertralinum
Thuốc điều trị về tâm thần
Thuốc Gốc
Small Molecule
CAS: 79617-96-2
ATC: N06AB06
ĐG : Actavis Group , http://www.actavis.com
CTHH: C17H17Cl2N
PTK: 306.23
Sertraline hydrochloride 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 (see Toxicity section below for a more detailed listing of side effects). Compared to other agents in this class, sertraline may cause greater diarrheal and male sexual dysfunction effects. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Sertraline may be used to treat major depressive disorder, obsessive-compulsive disorder (OCD), panic disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD) and social anxiety disorder (social phobia).
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H17Cl2N
Phân tử khối
306.23
Monoisotopic mass
305.073804963
InChI
InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1
InChI Key
InChIKey=VGKDLMBJGBXTGI-SJCJKPOMSA-N
IUPAC Name
(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
Traditional IUPAC Name
sertraline
SMILES
CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12
Độ tan chảy
243-245 °C
Độ hòa tan
3.5mg/L
logP
5.1
logS
-6.3
pKa (Strongest Basic)
9.85
PSA
12.03 Å2
Refractivity
85.74 m3·mol-1
Polarizability
32.44 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
1
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Ghose Filter
true
Dược Lực Học : Sertraline, an antidepressant drug similar to citalopram, fluoxetine, and paroxetine, is of the selective serotonin reuptake inhibitor (SSRI) type. Sertraline has one active metabolite and, like the other SSRIs, have less sedative, anticholinergic, and cardiovascular effects than the tricyclic antidepressant drugs because it does not have clinically important anticholinergic, antihistamine, or adrenergic blocking activity.
Cơ Chế Tác Dụng : Sertraline hydrochloride 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 (see Toxicity section below for a more detailed listing of side effects). Compared to other agents in this class, sertraline may cause greater diarrheal and male sexual dysfunction effects. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Sertraline may be used to treat major depressive disorder, obsessive-compulsive disorder (OCD), panic disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD) and social anxiety disorder (social phobia). The exact mechanism of action sertraline is not fully known, but the drug appears to selectively inhibit the reuptake of serotonin at the presynaptic membrane. This results in an increased synaptic concentration of serotonin in the CNS, which leads to numerous functional changes associated with enhanced serotonergic neurotransmission. It is suggested that these modifications are responsible for the antidepressant action observed during long term administration of antidepressants. It has also been hypothesized that obsessive-compulsive disorder is caused by the dysregulation of serotonin, as it is treated by sertraline, and the drug corrects this imbalance.
Dược Động Học :
▧ Absorption :
The effects of food on the bioavailability of the sertraline tablet and oral concentrate were studied in subjects administered a single dose with and without food. For the tablet, AUC was slightly increased when drug was administered with food but the Cmax was 25% greater, while the time to reach peak plasma concentration (Tmax) decreased from 8 hours post-dosing to 5.5 hours. For the oral concentrate, Tmax was slightly prolonged from 5.9 hours to 7.0 hours with food.
▧ Protein binding :
98% bound to serum proteins, principally to albumin and α1-acid glycoprotein
▧ Metabolism :
Extensively metabolized in the liver. Sertraline metabolism involves N-demethylation, N-hydroxylation, oxidative deamination, and glucuronidation of sertraline carbamic acid. Sertraline undergoes N-demethylation primarily catalyzed by cytochrome P450 (CYP) 2B6, with CYP2C19, CYP3A4 and CYP2D6 contributing to a lesser extent. Deamination occurs via CYP3A4 and CYP2C19. In vitro studies have shown that monoamine oxidase A and B may also catalyze sertraline deamination. Sertraline N-carbamoyl glucuronidation has also been observed in human liver microsomes.
▧ Route of Elimination :
Sertraline is extensively metabolized and excretion of unchanged drug in urine is a minor route of elimination.
▧ Half Life :
The elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours.
Độc Tính : Symptoms of toxicity include alopecia, decreased libido, diarrhea, ejaculation disorder, fatigue, insomnia, somnolence and serotonin syndrome. The most frequently observed side effects include: GI effects such as nausea, diarrhea or loose stools, dyspepsia, and dry mouth; nervous system effects such as somnolence, dizziness, insomnia, and tremor; sexual dysfunction in males (principally ejaculatory delay); and sweating.
Chỉ Định : For the management of major depressive disorder, posttraumatic stress disorder, obsessive-compulsive disorder, panic disorder with or without agoraphobia, premenstrual dysphoric disorder, social phobia, premature ejaculation, and vascular headaches.
Tương Tác Thuốc :
  • Almotriptan Increased risk of CNS adverse effects
  • Carbamazepine Sertraline increases the effect of carbamazepine
  • Carvedilol The SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, carvedilol.
  • Cilostazol Sertraline increases the effect of cilostazol
  • 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.
  • Donepezil Possible antagonism of action
  • Eletriptan Increased risk of CNS adverse effects
  • Erythromycin Possible serotoninergic syndrome with this combination
  • Fosphenytoin Sertraline increases the effect of hydantoin
  • Frovatriptan Increased risk of CNS adverse effects
  • Galantamine Possible antagonism of action
  • 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
  • Metoprolol The SSRI increases the effect of the beta-blocker
  • Moclobemide Possible severe adverse reaction with this combination
  • Naratriptan Increased risk of CNS adverse effects
  • Oxycodone Increased risk of serotonin syndrome
  • Phenelzine Possible severe adverse reaction with this combination
  • Phenytoin Sertraline increases the effect of hydantoin
  • Pimozide The SSRI, sertraline, increases the effect and toxicity of pimozide.
  • Propafenone Fluoxetine increases the effect and toxicity of propafenone
  • Propranolol The SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, propranolol.
  • Rasagiline Possible severe adverse reaction with this combination
  • Tamoxifen Sertraline may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Tamsulosin Sertraline, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Sertraline is initiated, discontinued, or dose changed.
  • Terbinafine Terbinafine may reduce the metabolism and clearance of Sertraline. Consider alternate therapy or monitor for therapeutic/adverse effects of Sertraline if Terbinafine is initiated, discontinued or dose changed.
  • Tiaprofenic acid Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
  • Tipranavir Tipranavir increases the concentration of Sertraline. The Sertraline dose may require an adjustment.
  • Tolmetin Increased antiplatelet effects may enhance the risk of bleeding. Alternate therapy may be considered or monitor for inreased bleeding during concomitant therapy.
  • Tolterodine Sertraline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
  • Tramadol Tramadol increases the risk of serotonin syndrome and seizures. Sertraline may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Sertraline may decrease the effect of Tramadol by decreasing active metabolite production.
  • 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, Sertraline. Monitor for increased bleeding during concomitant thearpy.
  • Trimipramine The SSRI, Sertraline, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Sertraline is initiated, discontinued or dose changed.
  • Triprolidine The CNS depressants, Triprolidine and Sertraline, 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.
  • Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and sertraline, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Liều Lượng & Cách Dùng : Capsule - Oral - 100 mg
Capsule - Oral - 25 mg
Capsule - Oral - 50 mg
Solution, concentrate - Oral - 20 mg/ml
Tablet, film coated - Oral - 100 mg
Tablet, film coated - Oral - 150 mg
Tablet, film coated - Oral - 200 mg
Tablet, film coated - Oral - 25 mg
Tablet, film coated - Oral - 50 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Apotex
    Sản phẩm biệt dược : Apo-Sertraline
  • Công ty :
    Sản phẩm biệt dược : Lustral
  • Công ty : Pfizer
    Sản phẩm biệt dược : Zoloft
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01104
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=68617
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505341
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07246
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02360
ChemSpider
http://www.chemspider.com/Chemical-Structure.61881.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0049-4960-30
PharmGKB
http://www.pharmgkb.org/drug/PA451333
Wikipedia
http://en.wikipedia.org/wiki/Sertraline
RxList
http://www.rxlist.com/cgi/generic/sertral.htm
Drugs.com
http://www.drugs.com/sertraline.html
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