Tìm theo
Theophylline
Các tên gọi khác (10 ) :
  • 1,3-dimethyl-7H-purine-2,6-dione
  • 1,3-dimethylxanthine
  • Elixophyllin
  • Respbid
  • Theo-dur
  • Theolair
  • Theophyllin
  • Theophylline
  • Theophylline Anhydrous
  • Uniphyl
Thuốc tác dụng trên đường hô hấp
Thuốc Gốc
Small Molecule
CAS: 58-55-9
ATC: R03DA04, R03DA05
ĐG : Actavis Group , http://www.actavis.com
CTHH: C7H8N4O2
PTK: 180.164
A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C7H8N4O2
Phân tử khối
180.164
Monoisotopic mass
180.06472552
InChI
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChI Key
InChIKey=ZFXYFBGIUFBOJW-UHFFFAOYSA-N
IUPAC Name
1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional IUPAC Name
theophylline
SMILES
CN1C2=C(NC=N2)C(=O)N(C)C1=O
Độ tan chảy
273 °C
Độ hòa tan
7360 mg/L (at 25 °C)
logP
-0.02
logS
-0.9
pKa (strongest acidic)
7.82
pKa (Strongest Basic)
-0.78
PSA
69.3 Å2
Refractivity
44.93 m3·mol-1
Polarizability
16.86 Å3
Rotatable Bond Count
0
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
caco2 Permeability
-4.35
pKa
8.81
Dược Lực Học : Theophylline, an xanthine derivative chemically similar to caffeine and theobromine, is used to treat asthma and bronchospasm. Theophylline has two distinct actions in the airways of patients with reversible (asthmatic) obstruction; smooth muscle relaxation (i.e., bronchodilation) and suppression of the response of the airways to stimuli (i.e., non-bronchodilator prophylactic effects).
Cơ Chế Tác Dụng : A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD. Theophylline relaxes the smooth muscle of the bronchial airways and pulmonary blood vessels and reduces airway responsiveness to histamine, methacholine, adenosine, and allergen. Theophylline competitively inhibits type III and type IV phosphodiesterase (PDE), the enzyme responsible for breaking down cyclic AMP in smooth muscle cells, possibly resulting in bronchodilation. Theophylline also binds to the adenosine A2B receptor and blocks adenosine mediated bronchoconstriction. In inflammatory states, theophylline activates histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones for transcription to begin.
Dược Động Học :
▧ Absorption :
Theophylline is rapidly and completely absorbed after oral administration in solution or immediate-release solid oral dosage form.
▧ Volume of Distribution :
* 0.3 to 0.7 L/kg
▧ Protein binding :
40%, primarily to albumin.
▧ Metabolism :
Hepatic. Biotransformation takes place through demethylation to 1-methylxanthine and 3-methylxanthine and hydroxylation to 1,3-dimethyluric acid. 1-methylxanthine is further hydroxylated, by xanthine oxidase, to 1-methyluric acid. About 6% of a theophylline dose is N-methylated to caffeine. Caffeine and 3-methylxanthine are the only theophylline metabolites with pharmacologic activity.
▧ Route of Elimination :
Theophylline does not undergo any appreciable pre-systemic elimination, distributes freely into fat-free tissues and is extensively metabolized in the liver. Renal excretion of unchanged theophylline in neonates amounts to about 50% of the dose, compared to about 10% in children older than three months and in adults.
▧ Half Life :
8 hours
▧ Clearance :
* 0.29 mL/kg/min [Premature neonates, postnatal age 3-15 days] * 0.64 mL/kg/min [Premature neonates, postnatal age 25-57 days] * 1.7 mL/kg/min [Children 1-4 years] * 1.6 mL/kg/min [Children 4-12 years] * 0.9 mL/kg/min [Children 13-15 years] * 1.4 mL/kg/min [Children 16-17 years] * 0.65 mL/kg/min [Adults (16-60 years), otherwise healthy non-smoking asthmatics] * 0.41 mL/kg/min [Elderly (>60 years), non-smokers with normal cardiac, liver, and renal function] * 0.33 mL/kg/min [Acute pulmonary edema] * 0.54 mL/kg/min [COPD >60 years, stable, non-smoker >1 year] * 0.48 mL/kg/min [COPD with cor pulmonale] * 1.25 mL/kg/min [Cystic fibrosis (14-28 years)] * 0.31 mL/kg/min [Liver disease cirrhosis] * 0.35 mL/kg/min [acute hepatitis] * 0.65 mL/kg/min [cholestasis] * 0.47 mL/kg/min [Sepsis with multi-organ failure] * 0.38 mL/kg/min [hypothyroid] * 0.8 mL/kg/min [hyperthyroid]
Độc Tính : Symptoms of overdose include seizures, arrhythmias, and GI effects.
Chỉ Định : For the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis.
Tương Tác Thuốc :
  • Aciclovir Acyclovir may increase the effect and toxicity of theophylline.
  • Adenosine Theophylline may decrease the effect of adenosine.
  • Amobarbital The barbiturate, amobarbital, decreases the effect of theophylline.
  • Aprobarbital The barbiturate, aprobarbital, decreases the effect of theophylline.
  • Atracurium Theophylline decreases the effect of the muscle relaxant
  • Bromazepam Theophylline may decrease the therapeutic effect of bromazepam. Monitor for changes in the therapeutic effects of bromazepam if theophylline is initiated, discontinued or dose changed.
  • Butabarbital The barbiturate, butabarbital, decreases the effect of theophylline.
  • Butalbital The barbiturate, butalbital, decreases the effect of theophylline.
  • Butethal The barbiturate, butethal, decreases the effect of theophylline.
  • Carbamazepine Carbamazepine may decrease the serum concentration of theophylline. Theophylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
  • Carteolol Antagonism of action and increased effect of theophylline
  • Cimetidine Cimetidine may increase the effect of theophylline.
  • Ciprofloxacin Ciprofloxacin may increase the effect of theophylline.
  • Clarithromycin Clarithromycin may increase the therapeutic and adverse effects of theophylline.
  • Dihydroquinidine barbiturate The barbiturate, dihydroquinidine barbiturate, decreases the effect of theophylline.
  • Disulfiram Disulfiram may increase the effect and toxicity of theophylline.
  • Doxacurium chloride Theophylline decreases the effect of the muscle relaxant
  • Enoxacin Enoxacin may increase the effect of theophylline.
  • Erythromycin The macrolide, erythromycin, may increase the effect and toxicity of theophylline.
  • Ethinyl Estradiol The contraceptive increases the effect and toxicity of theophylline
  • Ethotoin Decreased effect of both products
  • Febuxostat Coadministration of febuxostat with xanthine oxidase substrate drugs (azathioprine, mercaptopurine or theophylline) could increase plasma concentrations of these drugs, since these drugs are metabolized by xanthine oxidase, resulting in severe toxicity; hence their concomitant use is contraindicated. Since febuxostat does not inhibit or induce cytochrome P450 enzymes it lacks significant drug interactions with other drugs metabolized of these enzymes.
  • Fluvoxamine Fluvoxamine may increase the therapeutic and adverse effects of theophylline.
  • Fosphenytoin Decreased effect of both products
  • Grepafloxacin Grepafloxacin may increase the effect of theophylline.
  • Halothane Increased risk of cardiac arrhythmia
  • Heptabarbital The barbiturate, heptabarbital, decreases the effect of theophylline.
  • Hexobarbital The barbiturate, hexobarbital, decreases the effect of theophylline.
  • Interferon Alfa-2a, Recombinant Interferon increases the effect and toxicity of theophylline
  • Interferon Alfa-2b, Recombinant Interferon increases the effect and toxicity of theophylline
  • Interferon alfa-n1 Interferon increases the effect and toxicity of theophylline
  • Isoniazid Isoniazid may increase the therapeutic and adverse effects of theophylline.
  • Josamycin The macrolide, josamycin, may increase the effect and toxicity of theophylline.
  • Lithium Theophylline decreases serum levels of lithium
  • Mephenytoin Decreased effect of both products
  • Mestranol The contraceptive increases the effect and toxicity of theophylline
  • Methohexital The barbiturate, methohexital, decreases the effect of theophylline.
  • Methylphenobarbital The barbiturate, methylphenobarbital, decreases the effect of theophylline.
  • Metocurine Theophylline decreases the effect of the muscle relaxant
  • Mexiletine Mexiletine increases the effect and toxicity of theophylline
  • Mivacurium Theophylline decreases the effect of the muscle relaxant
  • Nadolol Antagonism of action and increased effect of theophylline
  • Norfloxacin Norfloxacin may increase the effect of theophylline.
  • Pancuronium Theophylline decreases the effect of the muscle relaxant
  • Pefloxacin Pefloxacin may increase the effect of theophylline.
  • Peginterferon alfa-2a Interferon increases the effect and toxicity of theophylline
  • Peginterferon alfa-2b Interferon increases the effect and toxicity of theophylline
  • Penbutolol Antagonism of action and increased effect of theophylline
  • Pentobarbital The barbiturate, pentobarbital, decreases the effect of theophylline.
  • Pentoxifylline Pentoxifylline increases the effect and toxicity of theophylline
  • Phenobarbital The barbiturate, phenobarbital, decreases the effect of theophylline.
  • Phenytoin Decreased effect of both products
  • Pindolol Antagonism of action and increased effect of theophylline
  • Primidone The barbiturate, primidone, decreases the effect of theophylline.
  • Propafenone Propafenone increases the effect of theophylline
  • Propranolol Antagonism of action and increased effect of theophylline
  • Quinidine barbiturate The barbiturate, quinidine barbiturate, decreases the effect of theophylline.
  • Regadenoson Non-specific adenosine receptor antagonist may interfere with the vasodilation activity of regadenoson. Avoid methylxanthines for at least 12 hours before administration of regadenoson.
  • Rifampicin Rifampin decreases the effect of theophylline
  • Ritonavir Ritonavir decreases the effect of theophylline
  • Rofecoxib Rofecoxib increases the effect and toxicity of theophylline
  • Secobarbital The barbiturate, secobarbital, decreases the effect of theophylline.
  • Sotalol Antagonism of action and increased effect of theophylline
  • St. John's Wort St. John's Wort decreases the effect of theophylline
  • Tacrine Tacrine may reduce the elimination rate of Theophylline. Monitor for changes in the therapeutic and toxic effects of theophylline if Tacrine is initiated, discontinued or if the dose is changed.
  • Talbutal The barbiturate, talbutal, decreases the effect of theophylline.
  • Telithromycin Telithromycin may reduce clearance of Theophylline. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Theophylline if Telithromycin is initiated, discontinued or dose changed.
  • Temazepam Theophylline may decrease the efficacy of Temazepam. Monitor for changes in the therapeutic effect of Temazepam if Theophylline is initiated, discontinued or dose changed.
  • Terbinafine Terbinafine increases the effect and toxicity of theophylline
  • Thiabendazole The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Theophylline by decreasing Theophylline metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Theophylline if Thiabendazole is initiated, discontinued or dose changed.
  • Ticlopidine Ticlopidine increases the effect and toxicity of theophylline
  • Timolol Antagonism of action and increased effect of theophylline
  • Tipranavir Tipranavir, co-administered with Ritonavir, may decrease the concentration of Theophylline.
  • Troleandomycin The macrolide, troleandomycin, may increase the effect and toxicity of theophylline.
  • Tubocurarine Theophylline decreases the effect of the muscle relaxant
  • Vecuronium Theophylline decreases the effect of the muscle relaxant
  • Verapamil Verapamil increases the effect of theophylline
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of theophylline by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of theophylline if voriconazole is initiated, discontinued or dose changed.
  • Zafirlukast Zafirlukast serum concentrations may be decreased by Theophylline.
  • Zileuton Zileuton may increase the therapeutic and adverse effects of theophylline by increasing its serum concentration. Monitor for changes in the therapeutic and adverse effects of theophylline if zileuton is initiated, discontinued or dose changed. Dose alterations should be considered.
Liều Lượng & Cách Dùng : Elixir - Oral
Liquid - Oral
Solution - Intravenous
Tablet - Oral
Tablet, extended release - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Elixophyllin
  • Công ty :
    Sản phẩm biệt dược : Quibron-T
  • Công ty :
    Sản phẩm biệt dược : Respbid
  • Công ty :
    Sản phẩm biệt dược : Slo-Bid
  • Công ty :
    Sản phẩm biệt dược : Theo 24
  • Công ty :
    Sản phẩm biệt dược : Theo-24
  • Công ty :
    Sản phẩm biệt dược : Theo-Dur
  • Công ty :
    Sản phẩm biệt dược : Theodur G
  • Công ty :
    Sản phẩm biệt dược : Theolair
  • Công ty :
    Sản phẩm biệt dược : Theophylline(Anhydrous)
  • Công ty :
    Sản phẩm biệt dược : Uniphyl
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00277
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2153
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505949
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07130
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00371
ChemSpider
http://www.chemspider.com/Chemical-Structure.2068.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=10847
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0089-0342-10
PharmGKB
http://www.pharmgkb.org/drug/PA451647
Wikipedia
http://en.wikipedia.org/wiki/Theophylline
RxList
http://www.rxlist.com/cgi/generic/theosr.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/the1440.shtml
Drugs.com
http://www.drugs.com/cdi/theophylline.html
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