Doxepin

Các tên gọi khác (4 ) :

Cidoxepin
Doxepin
Sinequan
Zonalon

adrenergic uptake inhibitors, antidepressive agents

Thuốc Gốc

Small Molecule

CAS: 1668-19-5

ATC: N06AA12

ĐG : Advanced Pharmaceutical Services Inc.

CTHH: C₁₉H₂₁NO

PTK: 279.3761

Doxepin hydrochloride is a dibenzoxepin-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, doxepin does not affect mood or arousal, but may cause sedation. In depressed individuals, doxepin exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as doxepin and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also 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. Doxepin has less sedative and anticholinergic effects than amitriptyline. See toxicity section below for a complete listing of side effects. Doxepin may be used to treat depression and insomnia. Unlabeled indications include chronic and neuropathic pain, and anxiety. Doxepin may also be used as a second line agent to treat idiopathic urticaria.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₉H₂₁NO

Phân tử khối

279.3761

Monoisotopic mass

279.162314299

InChI

InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11-

InChI Key

InChIKey=ODQWQRRAPPTVAG-BOPFTXTBSA-N

IUPAC Name

dimethyl(3-{9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine

Traditional IUPAC Name

dimethyl(3-{9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine

SMILES

[H]C(CCN(C)C)=C1C2=CC=CC=C2COC2=CC=CC=C12

Độ tan chảy

< 25 °C

Độ sôi

265 °C at 2.00E-01 mm Hg

Độ hòa tan

31.6 mg/L (at 25 °C)

logP

4.29

logS

-3.4

pKa (Strongest Basic)

9.76

PSA

12.47 Å²

Refractivity

98.24 m³·mol^-1

Polarizability

32.47 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : Doxepin, a tricyclic antidepressant of the dibenzoxepin type, is used to treat depression and anxiety and, topically, pruritus associated with eczema. Doxepin has substantial anticholinergic and sedative effects. The E (trans)-isomer is more active as a serotonin reuptake inhibitor while the Z-isomer acts as a sedative.

Cơ Chế Tác Dụng : Doxepin hydrochloride is a dibenzoxepin-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, doxepin does not affect mood or arousal, but may cause sedation. In depressed individuals, doxepin exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as doxepin and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also 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. Doxepin has less sedative and anticholinergic effects than amitriptyline. See toxicity section below for a complete listing of side effects. Doxepin may be used to treat depression and insomnia. Unlabeled indications include chronic and neuropathic pain, and anxiety. Doxepin may also be used as a second line agent to treat idiopathic urticaria. The mechanism of action of doxepin is not completely understood. It is thought that like amitriptyline, doxepin enhances the actions of norepinephrine and serotonin by blocking their reuptake at the neuronal membrane. However, doxepin weakly inhibits the reuptake of dopamine. Doxepin may also act on histamine H₁-receptors, resulting in sedative effects, and β-adrenergic receptors. It is also an antagonist of 5-hydroxytryptamine (serotonin) receptors, alpha-1 adrenergic receptor, and muscarinic cholinergic receptors.

Dược Động Học :

▧ Absorption :
Well-absorbed from the GI tract. Peak plasma concentrations occur within 2 hours of oral administration.
▧ Protein binding :
Doxepin and desmethyldoxepin is 80% protein bound. It is also a lipophillic drug and is capable of crossing the blood-brain-barrier.
▧ Metabolism :
Extensively metabolized in the liver via the same pathways as other TCAs. N-demethylation produces an active metabolite, N-desmethyldoxepin. CYP2D6 specifically hydroxylates the E-isomer.
▧ Half Life :
6 - 24.5 hours

Độc Tính : LD₅₀=26 (mg/kg) (in mice, iv); LD₅₀=16 (mg/kg) (in rats, iv); Cardiac dysrhythmias, severe hypotension, convulsions, and CNS depression, including coma. Changes in the electrocardiogram, particularly in QRS axis or width, are clinically significant indicators of tricyclic antidepressant toxicity. Side effects include: 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 : Doxepin is used for the treatment of depression and/or anxiety. It can also be used for chronic urticaria and in the management of pain.

Tương Tác Thuốc :

Altretamine Risk of severe hypotension
Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Atazanavir Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if atazanavir if initiated, discontinued or dose changed.
Butabarbital Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like doxepin. 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 doxepin. 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.
Carbamazepine Carbamazepine may decrease the serum concentration of the tricyclic antidepressant, doxepin, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if carbamazepine is initiated, discontinued or dose changed.
Cimetidine Cimetidine may increase the effect of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if cimetidine is initiated, discontinued or dose changed.
Cisapride Increased risk of cardiotoxicity and arrhythmias
Clonidine The tricyclic antidepressant, doxepin, decreases the effect of clonidine.
Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dihydroquinidine barbiturate Dihydroquinidine barbiturate increases the effect of the tricyclic antidepressant, doxepin.
Dobutamine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of dobutamine.
Donepezil Possible antagonism of action
Dopamine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of dopamine.
Ephedra The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of ephedra.
Ephedrine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of ephedrine.
Epinephrine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of epinephrine.
Fenoterol The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of fenoterol.
Fluoxetine The SSRI, fluoxetine, may increase the serum concentration of the tricyclic antidepressant, doxepin, 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 doxepin if fluoxetine is initiated, discontinued or dose changed.
Fluvoxamine The SSRI, fluvoxamine, may increase the serum concentration of the tricyclic antidepressant, doxepin, 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 doxepin if fluvoxamine is initiated, discontinued or dose changed.
Galantamine Possible antagonism of action
Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
Guanethidine The tricyclic antidepressant, doxepin, decreases the effect of guanethidine.
Isocarboxazid Possibility of severe adverse effects
Isoprenaline The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of isoproterenol.
Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Mephentermine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of mephentermine.
Mesoridazine Increased risk of cardiotoxicity and arrhythmias
Metaraminol The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of metaraminol.
Methoxamine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of methoxamine.
Moclobemide Possible severe adverse reaction with this combination
Norepinephrine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of norepinephrine.
Orciprenaline The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of orciprenaline.
Phenelzine Possibility of severe adverse effects
Phenylephrine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of phenylephrine.
Phenylpropanolamine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of phenylpropanolamine.
Pirbuterol The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of pirbuterol.
Procaterol The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of procaterol.
Pseudoephedrine The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of pseudoephedrine.
Quinidine Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
Quinidine barbiturate Quinidine barbiturate increases the effect of tricyclic antidepressant, doxepin.
Rasagiline Possibility of severe adverse effects
Rifabutin The rifamycin, rifabutin, may decrease the effect of the tricyclic antidepressant, doxepin, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if rifabutin is initiated, discontinued or dose changed.
Rifampicin The rifamycin, rifampin, may decrease the effect of the tricyclic antidepressant, doxepin, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if rifampin is initiated, discontinued or dose changed.
Ritonavir Ritonavir may increase the effect and toxicity of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if ritonavir if initiated, discontinued or dose changed.
Rivastigmine Possible antagonism of action
Salbutamol The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of salbutamol.
Sibutramine Increased risk of CNS adverse effects
Sparfloxacin Increased risk of cardiotoxicity and arrhythmias
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Doxepin, 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.
Telithromycin Telithromycin may reduce clearance of Doxepin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Doxepin if Telithromycin is initiated, discontinued or dose changed.
Terbinafine Terbinafine may reduce the metabolism and clearance of Doxepin. Consider alternate therapy or monitor for therapeutic/adverse effects of Amytriptyline if Doxepin is initiated, discontinued or dose changed.
Terbutaline The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of terbutaline.
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Thiabendazole The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Doxepin by decreasing Doxepin metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Doxepin if Thiabendazole is initiated, discontinued or dose changed.
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.
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 Doxepin, 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 Doxepin, 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 Doxepin, 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. Voriconazole, a strong CYP3A4 inhibitor, may also increase the serum concentration of doxepin by decreasing its metabolism. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of doxepin if voriconazole 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 is contraindicated.
Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and doxepin, 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 : Capsule - Oral - 10 mg, 25 mg, 50 mg, 75 mg, 100 mg, 150 mg
Concentrate - Oral - 10 mg/mL
Cream - Topical - 5%
Tablet - Oral - 3 mg, 6 mg

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Novo-Doxepin 150 mg Capsule

Giá bán buôn : USD >1.18

Đơn vị tính : capsule
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Giá bán buôn : USD >1.22

Đơn vị tính : capsule
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Giá bán buôn : USD >3.05

Đơn vị tính : g
Biệt dược thương mại : Doxepin 150 mg capsule

Giá bán buôn : USD >3.33

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin hcl powder

Giá bán buôn : USD >8.88

Đơn vị tính : g
Biệt dược thương mại : Zonalon 5% Cream 30 gm Tube

Giá bán buôn : USD >144.29

Đơn vị tính : tube
Biệt dược thương mại : Zonalon 5% Cream 45 gm Tube

Giá bán buôn : USD >190.13

Đơn vị tính : tube
Biệt dược thương mại : Doxepin HCl 10 mg/ml Concentrate

Giá bán buôn : USD >0.13

Đơn vị tính : ml
Biệt dược thương mại : Doxepin 100 mg capsule

Giá bán buôn : USD >0.14

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin 25 mg capsule

Giá bán buôn : USD >0.18

Đơn vị tính : capsule
Biệt dược thương mại : Apo-Doxepin 25 mg Capsule

Giá bán buôn : USD >0.19

Đơn vị tính : capsule
Biệt dược thương mại : Novo-Doxepin 25 mg Capsule

Giá bán buôn : USD >0.19

Đơn vị tính : capsule
Biệt dược thương mại : Apo-Doxepin 10 mg Capsule

Giá bán buôn : USD >0.2

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin 75 mg capsule

Giá bán buôn : USD >0.21

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin HCl 10 mg capsule

Giá bán buôn : USD >0.21

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin HCl 25 mg capsule

Giá bán buôn : USD >0.23

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin HCl 50 mg capsule

Giá bán buôn : USD >0.25

Đơn vị tính : capsule
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Đơn vị tính : capsule
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Giá bán buôn : USD >0.32

Đơn vị tính : capsule
Biệt dược thương mại : Sinequan 25 mg Capsule

Giá bán buôn : USD >0.35

Đơn vị tính : capsule
Biệt dược thương mại : Apo-Doxepin 50 mg Capsule

Giá bán buôn : USD >0.36

Đơn vị tính : capsule
Biệt dược thương mại : Novo-Doxepin 50 mg Capsule

Giá bán buôn : USD >0.36

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin HCl 75 mg capsule

Giá bán buôn : USD >0.43

Đơn vị tính : capsule
Biệt dược thương mại : Apo-Doxepin 75 mg Capsule

Giá bán buôn : USD >0.52

Đơn vị tính : capsule
Biệt dược thương mại : Novo-Doxepin 75 mg Capsule

Giá bán buôn : USD >0.52

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin HCl 100 mg capsule

Giá bán buôn : USD >0.56

Đơn vị tính : capsule
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Giá bán buôn : USD >0.57

Đơn vị tính : capsule
Biệt dược thương mại : Sinequan 50 mg Capsule

Giá bán buôn : USD >0.64

Đơn vị tính : capsule
Biệt dược thương mại : Apo-Doxepin 100 mg Capsule

Giá bán buôn : USD >0.68

Đơn vị tính : capsule
Biệt dược thương mại : Novo-Doxepin 100 mg Capsule

Giá bán buôn : USD >0.68

Đơn vị tính : capsule
Biệt dược thương mại : Doxepin HCl 150 mg capsule

Giá bán buôn : USD >0.87

Đơn vị tính : capsule
Biệt dược thương mại : Zonalon 5% cream

Giá bán buôn : USD >0.89

Đơn vị tính : g
Biệt dược thương mại : Sinequan 75 mg Capsule

Giá bán buôn : USD >0.93

Đơn vị tính : capsule

Nhà Sản Xuất

Công ty : PennwaIt

Sản phẩm biệt dược : Adapin
Công ty : Pfizer

Sản phẩm biệt dược : Aponal
Công ty :

Sản phẩm biệt dược : Curatin
Công ty : Shou Chan

Sản phẩm biệt dược : Doxepine
Công ty :

Sản phẩm biệt dược : Prudoxin
Công ty : Lexphar

Sản phẩm biệt dược : Quitaxon
Công ty : Somaxon Pharmaceuticals, Inc.

Sản phẩm biệt dược : Silenor
Công ty : Pfizer

Sản phẩm biệt dược : Sinequan
Công ty : Fougera

Sản phẩm biệt dược : Zonalon

Đóng gói

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Công ty : Amerisource Health Services Corp.

Website : http://www.amerisourcebergen.com
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Công ty : Pharmaceutical Utilization Management Program VA Inc.
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Công ty : Preferred Pharmaceuticals Inc.

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Công ty : Prepackage Specialists
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Website : http://www.prepaksys.com
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Công ty : Rebel Distributors Corp.

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Công ty : Southwood Pharmaceuticals

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Công ty : Stat Rx Usa

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Công ty : Teva Pharmaceutical Industries Ltd.

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Công ty : UDL Laboratories

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Công ty : United Research Laboratories Inc.

Website : http://www.urlpharma.com
Công ty : Watson Pharmaceuticals

Website : http://www.watson.com
Công ty : Wockhardt Ltd.

Website : http://www.wockhardtin.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01142

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C06971

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D07875

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-1049-01

PharmGKB

http://www.pharmgkb.org/drug/PA449409

Wikipedia

http://en.wikipedia.org/wiki/Doxepin

RxList

http://www.rxlist.com/cgi/generic/doxepin.htm

Drugs.com

http://www.drugs.com/cdi/doxepin-capsules.html

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