Tìm theo
Protriptyline
Các tên gọi khác (11 ) :
  • 3-(5H-dibenzo[a,d][7]annulen-5-yl)-N-methylpropan-1-amine
  • 3-(5H-Dibenzo[a,D]cyclohepten-5-yl)-N-methyl-1-propanamine
  • 5-(3-Methylaminopropyl)-5H-dibenzo[a,D]cycloheptene
  • 7-(3-Methylaminopropyl)-1,2:5,6-dibenzocycloheptatriene
  • Amimetilina
  • N-Methyl-5H-dibenzo[a,D]cycloheptene-5-propanamine
  • N-Methyl-5H-dibenzo[a,D]cycloheptene-5-propylamine
  • Protriptilina
  • Protriptylin
  • Protriptyline
  • Protriptylinum
adrenergic uptake inhibitors, antidepressive agents tricyclic
Thuốc Gốc
Small Molecule
CAS: 438-60-8
ATC: N06AA11
ĐG : Barr Pharmaceuticals
CTHH: C19H21N
PTK: 263.3767
Protriptyline hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, protriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, protriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. In addition, TCAs down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Protriptyline may be used for the treatment of depression.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C19H21N
Phân tử khối
263.3767
Monoisotopic mass
263.167399677
InChI
InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3
InChI Key
InChIKey=BWPIARFWQZKAIA-UHFFFAOYSA-N
IUPAC Name
methyl(3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl}propyl)amine
Traditional IUPAC Name
protriptyline
SMILES
CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12
Độ tan chảy
169-171 °C (Protriptyline HCl)
Độ hòa tan
1.04 mg/L
logP
4.7
logS
-6.1
pKa (Strongest Basic)
10.54
PSA
12.03 Å2
Refractivity
87.3 m3·mol-1
Polarizability
31.6 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
1
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Protriptyline is a tricyclic antidepressant. It was thought that tricyclic antidepressants work by inhibiting the reuptake of the neurotransmitters norepinephrine and serotonin by nerve cells. However, this response occurs immediately, yet mood does not lift for approximately two weeks. It is now thought that changes occur in receptor sensitivity in the cerebral cortex and hippocampus. The hippocampus is part of the limbic system, a part of the brain involved in emotions. Presynaptic receptors are affected: α1 and β1 receptors are sensitized, α2 receptors are desensitised (leading to increased noradrenaline production). Tricyclics are also known as effective analgesics for different types of pain, especially neuropathic or neuralgic pain. A precise mechanism for their analgesic action is unknown, but it is thought that they modulate anti-pain opioid systems in the CNS via an indirect serotonergic route. They are also effective in migraine prophylaxis, but not in abortion of acute migraine attack. The mechanism of their anti-migraine action is also thought to be serotonergic.
Cơ Chế Tác Dụng : Protriptyline hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, protriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, protriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. In addition, TCAs down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Protriptyline may be used for the treatment of depression. Protriptyline acts by decreasing the reuptake of norepinephrine and serotonin (5-HT).
Dược Động Học :

▧ Route of Elimination :
Cumulative urinary excretion during 16 days accounted for approximately 50% of the drug. The fecal route of excretion did not seem to be important.
Độc Tính : Side effects include anxiety, blood disorders, confusion, decreased libido, dizziness, flushing, headache, impotence, insomnia, low blood pressure, nightmares, rapid or irregular heartbeat, rash, seizures, sensitivity to sunlight, stomach and intestinal discomfort, sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
Chỉ Định : For the treatment of depression.
Tương Tác Thuốc :
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Atazanavir Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of protriptyline if atazanavir if initiated, discontinued or dose changed.
  • Butabarbital Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like protriptyline. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
  • Butalbital Barbiturates such as butalbital may increase the metabolism of tricyclic antidepressants such as protriptyline. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
  • Cimetidine Cimetidine may increase the effect of tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of trimipramine if cimetidine is initiated, discontinued or dose changed.
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Clonidine The tricyclic antidepressant, protriptyline, decreases the effect of clonidine.
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Donepezil Possible antagonism of action
  • Epinephrine The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of epinephrine.
  • Fenoterol The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of fenoterol.
  • Fluoxetine The SSRI, fluoxetine, may increase the serum concentration of the tricyclic antidepressant, protriptyline, by decreasing its metabolism. Additive modulation of serotonin activity also increases the risk of serotonin syndrome. Monitor for development of serotonin syndrome during concomitant therapy. Monitor for changes in the therapeutic and adverse effects of protriptyline if fluoxetine is initiated, discontinued or dose changed.
  • Fluvoxamine The SSRI, fluvoxamine, may increase the serum concentration of the tricyclic antidepressant, protriptyline, by decreasing its metabolism. Additive modulation of serotonin activity also increases the risk of serotonin syndrome. Monitor for development of serotonin syndrome during concomitant therapy. Monitor for changes in the therapeutic and adverse effects of protriptyline if fluvoxamine is initiated, discontinued or dose changed.
  • Galantamine Possible antagonism of action
  • Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
  • Guanethidine The tricyclic antidepressant, protriptyline, decreases the effect of guanethidine.
  • Isocarboxazid Possibility of severe adverse effects
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Moclobemide Possible severe adverse reaction with this combination
  • Orciprenaline The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of orciprenaline.
  • Phenelzine Possibility of severe adverse effects
  • Phenylephrine The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of phenylephrine.
  • Phenylpropanolamine The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of phenylpropanolamine.
  • Pseudoephedrine The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of pseudoephedrine.
  • Quinidine Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of protriptyline if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Rasagiline Possibility of severe adverse effects
  • Rifabutin The rifamycin, rifabutin, may decrease the effect of the tricyclic antidepressant, protriptyline, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of protriptyline if rifabutin is initiated, discontinued or dose changed.
  • Rifampicin The rifamycin, rifampin, may decrease the effect of the tricyclic antidepressant, protriptyline, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of protriptyline if rifampin is initiated, discontinued or dose changed.
  • Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Protriptyline, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
  • Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Terbinafine Terbinafine may reduce the metabolism and clearance of Protriptyline. Consider alternate therapy or monitor for therapeutic/adverse effects of Protriptyline if Terbinafine is initiated, discontinued or dose changed.
  • Terbutaline The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of terbutaline.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Thiothixene May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
  • Toremifene Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
  • Tramadol Tramadol increases 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.
  • Trimethobenzamide Trimethobenzamide and Protriptyline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
  • Trimipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome. Additive QTc-prolongation may also occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Triprolidine Triprolidine and Protriptyline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
  • Trospium Trospium and Protriptyline, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
  • Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Voriconazole Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
  • Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and protriptyline, increases 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 : Tablet, film coated - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Roxane
    Sản phẩm biệt dược : Protriptyline Hydrochloride
  • Công ty :
    Sản phẩm biệt dược : Triptil
  • Công ty : Odyssey
    Sản phẩm biệt dược : Vivactil
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00344
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4976
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505128
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07408
ChemSpider
http://www.chemspider.com/Chemical-Structure.4805.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0555-0595-02
PharmGKB
http://www.pharmgkb.org/drug/PA451168
Wikipedia
http://en.wikipedia.org/wiki/Protriptyline
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/viv1617.shtml
Drugs.com
http://www.drugs.com/cdi/protriptyline.html
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