Tìm theo
Chlorpromazine
Các tên gọi khác (14 ) :
  • 3-(2-chloro-10H-Phenothiazin-10-yl)-N,N-dimethyl-1-propanamine
  • 3-(2-Chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
  • Aminazine
  • Chlorderazin
  • Chloropromazine
  • Chlorpromados
  • Chlorpromazine
  • Chlorpromazinum
  • Clorpromazina
  • Contomin
  • CPZ
  • Largactil
  • N-(3-Dimethylaminopropyl)-3-chlorophenothiazine
  • Thorazine
Thuốc điều trị về tâm thần
Thuốc Gốc
Small Molecule
CAS: 50-53-3
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C17H19ClN2S
PTK: 318.864
The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class, chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking dopamine receptors. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H19ClN2S
Phân tử khối
318.864
Monoisotopic mass
318.095747015
InChI
InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3
InChI Key
InChIKey=ZPEIMTDSQAKGNT-UHFFFAOYSA-N
IUPAC Name
[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine
Traditional IUPAC Name
chlorpromazine
SMILES
CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2
Độ tan chảy
177-178
Độ sôi
200-205 °C at 8.00E-01 mm Hg
Độ hòa tan
2.55 mg/L (at 24 °C)
logP
5.41
logS
-5.01
pKa (Strongest Basic)
9.2
PSA
6.48 Å2
Refractivity
93.76 m3·mol-1
Polarizability
35.1 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
2
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
caco2 Permeability
-4.7
pKa
9.3 (at 25 °C)
Dược Lực Học : Chlorpromazine is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Chlorpromazine has actions at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Chlorpromazine has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
Cơ Chế Tác Dụng : The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class, chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking dopamine receptors. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup. [PubChem] Chlorpromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Additionally, Chlorpromazine is a weak presynaptic inhibitor of Dopamine reuptake, which may lead to (mild) antidepressive and antiparkinsonian effects. This action could also account for psychomotor agitation and amplification of psychosis (very rarely noted in clinical use).
Dược Động Học :
▧ Absorption :
Readily absorbed from the GI tract. Bioavailability varies due to first-pass metabolism by the liver.
▧ Volume of Distribution :
* 20 L/kg
▧ Protein binding :
> 90% to plasma proteins, primarily albumin
▧ Metabolism :
Extensively metabolized in the liver and kidneys. It is extensively metabolized by cytochrome P450 isozymes CYP2D6 (major pathway), CYP1A2 and CYP3A4. Approximately 10 to 12 major metabolite have been identified. Hydroxylation at positions 3 and 7 of the phenothiazine nucleus and the N-dimethylaminopropyl side chain undergoes demethylation and is also metabolized to an N-oxide. In urine, 20% of chlopromazine and its metabolites are excreted unconjugated in the urine as unchanged drug, demonomethylchlorpromazine, dedimethylchlorpromazine, their sulfoxide metabolites, and chlorpromazine-N-oxide. The remaining 80% consists of conjugated metabolites, principally O-glucuronides and small amounts of ethereal sulfates of the mono- and dihydroxy-derivatives of chlorpromazine and their sulfoxide metabolites. The major metabolites are the monoglucuronide of N-dedimethylchlorpromazine and 7-hydroxychlorpromazine. Approximately 37% of the administered dose of chlorpromazine is excreted in urine.
▧ Route of Elimination :
Kidneys, ~ 37% excreted in urine
▧ Half Life :
~ 30 hours
Độc Tính : Agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, restlessness
Chỉ Định : For the treatment of schizophrenia, control nausea and vomiting, For relief of restlessness and apprehension before surgery, adjunct in the treatment of tetanus, control the manifestations of the manic type of manic-depressive illness.
Tương Tác Thuốc :
  • Amphetamine Decreased anorexic effect, may increase psychotic symptoms
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Benzphetamine Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
  • Bromocriptine The phenothiazine decreases the effect of bromocriptine
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Dexfenfluramine Decreased anorexic effect, may increase psychotic symptoms.
  • Dextroamphetamine Decreased anorexic effect, may increases psychotic symptoms
  • Diethylpropion Decreased anorexic effect, may increase psychotic symptoms
  • Dihydrocodeine Phenothiazines may enhance hypotensive effects of opioid analgesics. It is recommended to monitor patients for hypotension.
  • Donepezil Possible antagonism of action
  • Fenfluramine Decreased anorexic effect, may increase psychotic symptoms
  • Galantamine Possible antagonism of action
  • Gatifloxacin Increased risk of cardiotoxicity and arrhythmias
  • Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
  • Guanethidine Chlorpromazine may decrease the effect of guanethidine.
  • Levofloxacin Increased risk of cardiotoxicity and arrhythmias
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Mazindol Decreased anorexic effect, may increase psychotic symptoms
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Methamphetamine Decreased anorexic effect, may increases psychotic symptoms
  • Metrizamide Increased risk of convulsions
  • Pethidine Increased sedation and hypotension
  • Phendimetrazine Decreased anorexic effect, may increases psychotic symptoms
  • Phenmetrazine Decreased anorexic effect, may increase psychotic symptoms
  • Phentermine Decreased anorexic effect, may increase psychotic symptoms
  • Phenylpropanolamine Decreased anorexic effect, may increase psychotic symptoms
  • Pindolol Increased effect of both drugs
  • Propranolol Increased effect of both drugs
  • Rivastigmine Possible antagonism of action
  • Sparfloxacin Increased risk of cardiotoxicity and arrhythmias
  • Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor (AChEI), Tacrine, and/or the anticholinergic/antipsychotic, Chlorpromazine, may be reduced due to antagonism. This interaction may be beneficial when the anticholinergic action is a side effect. AChEIs may also augment the central neurotoxic effect of antipsychotics. Monitor for extrapyramidal symptoms and 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.
  • Tamoxifen Chlorpromazine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Tamsulosin Chlorpromazine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Chlorpromazine is initiated, discontinued, or dose changed.
  • Terbinafine Terbinafine may reduce the metabolism and clearance of Chlorpromazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Chlorpromazine if Terbinafine is initiated, discontinued or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Tetrabenazine May cause dopamine deficiency. Similar pharmacologic properties thus combination therapy will worsen the severity of sedative, parkinsonian, and extrapyramidal adverse effects.
  • Thioridazine 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.
  • Tolterodine Chlorpromazine may decrease the metabolism and clearance of Tolterodine. Monitor for adverse/toxic effects of Tolterodine.
  • 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 Chlorpromazine may decrease the effect of Tramadol by decreasing active metabolite production.
  • Trimethobenzamide Trimethobenzamide and Chlorpromazine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
  • Trimipramine Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Chlorpromazine, a strong CYP2D6 inhibitor, may also decrease the metabolism and clearance of Trimipramine, a CYP2D6 substrate. Caution should be used during concomitant therapy.
  • Triprolidine The antihistamine, Triprolidine, may increase the arrhythmogenic effect of the phenothiazine, Chlorpromazine. Monitor for symptoms of ventricular arrhythmias. Additive anticholinergic and CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
  • Trospium Trospium and Chlorpromazine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
  • Venlafaxine Chlorpromazine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Chlorpromazine is initiated, discontinued, or dose changed.
  • 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 should be avoided.
  • 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). Chlorpromazine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if chlorpromazine is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Injection, solution - Parenteral - 25 mg/ml
Solution - Oral - 10 mg/5 ml
Solution, concentrate - Oral - 100 mg/ml
Solution, concentrate - Oral - 30 mg/ml
Suppository - Rectal - 25 mg
Suppository - Rectal - 50 mg
Tablet - Oral - 10 mg
Tablet - Oral - 100 mg
Tablet - Oral - 200 mg
Tablet - Oral - 25 mg
Tablet - Oral - 50 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Sản phẩm biệt dược : Chlorpromanyl
  • Công ty : Specia
    Sản phẩm biệt dược : Largactil
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Thorazine
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00477
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2726
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508395
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06906
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00270
ChemSpider
http://www.chemspider.com/Chemical-Structure.2625.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0781-1715-01
PharmGKB
http://www.pharmgkb.org/drug/PA448964
Wikipedia
http://en.wikipedia.org/wiki/Chlorpromazine
RxList
http://www.rxlist.com/cgi/generic3/chlorpromazine.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/chl1441.shtml
Drugs.com
http://www.drugs.com/cdi/chlorpromazine.html
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