Tìm theo
Budesonide
Các tên gọi khác (1) :
  • (11beta,16alpha)-16,17-(Butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dione
Thuốc tác dụng trên đường hô hấp
Thuốc Gốc
Small Molecule
CAS: 51333-22-3
ATC: A07EA06, D07AC09, R01AD05, R03BA02
ĐG : 3M Health Care , http://www.3m.com
CTHH: C25H34O6
PTK: 430.5339
Budesonide is a glucocorticoid used in the management of asthma, the treatment of various skin disorders, and allergic rhinitis. [PubChem] The extended release oral tablet, marketed as Uceris, was FDA approved on January 14, 2013 for the management of ulcerative colitis. Budesonide is provided as a mixture of two epimers (22R and 22S). Interestingly, the 22R form is two times more active than the 22S epimer. The two forms do not interconvert.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C25H34O6
Phân tử khối
430.5339
Monoisotopic mass
430.23553882
InChI
InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1
InChI Key
InChIKey=VOVIALXJUBGFJZ-KWVAZRHASA-N
IUPAC Name
(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
Traditional IUPAC Name
budesonide
SMILES
[H][C@@]12C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Độ tan chảy
226°C
Độ hòa tan
insoluble
logP
1.9
logS
-4
pKa (strongest acidic)
13.74
pKa (Strongest Basic)
-2.9
PSA
93.06 Å2
Refractivity
116.11 m3·mol-1
Polarizability
47.11 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
6
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
5
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Budesonide has a high glucocorticoid effect and a weak mineralocorticoid effect. It binds to the glucocorticoid receptor with a higher binding affinity than cortisol and prednisolone. When budesonide is systemically administered, suppression of endogenous cortisol concentrations and an impairment of the hypothalamus-pituitary-adrenal (HPA) axis function has been observed. Furthermore, a decrease in airway reactivity to histamine and other entities has been observed with the inhaled formulation. Generally, the inhaled formulation has a rapid onset action and improvement in asthma control can occur within 24 hours of initiation of treatment.
Cơ Chế Tác Dụng : Budesonide is a glucocorticoid used in the management of asthma, the treatment of various skin disorders, and allergic rhinitis. [PubChem] The extended release oral tablet, marketed as Uceris, was FDA approved on January 14, 2013 for the management of ulcerative colitis. Budesonide is provided as a mixture of two epimers (22R and 22S). Interestingly, the 22R form is two times more active than the 22S epimer. The two forms do not interconvert. Budesonide is an anti-inflammatory corticosteroid that exhibits potent glucocorticoid activity and weak mineralocorticoid activity. The precise mechanism of corticosteroid actions on inflammation in asthma, Crohn's disease, or ulcerative colitis is not known. Inflammation is an important component in the pathogenesis of asthma. Corticosteroids have been shown to have a wide range of inhibitory activities against multiple cell types (eg, mast cells, eosinophils, neutrophils, macrophages, and lymphocytes) and mediators (eg, histamine, eicosanoids, leukotrienes, and cytokines) involved in allergic and non-allergic-mediated inflammation. These anti-inflammatory actions of corticosteroids may contribute to their efficacy in the aforementioned diseases. Because budesonide undergoes significant first-pass elimination, the both oral preparations are formulated as an extended release tablet. As a result, budesonide release is delyaed until exposure to a pH ≥ 7 in the small intestine.
Dược Động Học :
▧ Absorption :
Absorption is complete following oral administration. The pharmacokinetic parameters of the inhaled powder formulation are as follows: Tmax = 30 minutes; Absolute systemic availability = 39%. When a single oral administration of 9 mg of Uceris are given, the pharmacokinetic parameters are as follows: Tmax = 13.3 ± 5.9 hours; Cmax = 1.35 ± 0.96 ng/mL; AUC = 16.43 ± 10.52 ng·hr/mL. It is important to note that the parameters have a high degree of variability. When a single oral administration of Entocort EC are given, the pharmacokinetic parameters are as follows: Tmax = 3- 600 minutes; Cmax = 5 nmol/L; AUC = 30 nmol•hr/L.
▧ Volume of Distribution :
Tablet and capsule, healthy subjects and patients = 2.2 - 3.9 L/kg; Powder, metered = 3 L/kg
▧ Protein binding :
85-90% protein bound.
▧ Metabolism :
Following absorption, budesonide is subject to high first pass metabolism (80-90%). Budesonide is rapidly and extensively biotransformed, mainly by CYP3A4, to its 2 major metabolites, 6b-hydroxybudesonide and 16a- hydroxyprednisolone. The glucocorticoid activity of these metabolites is negligible (<1/100) in relation to that of the parent compound.
▧ Route of Elimination :
Budesonide is excreted in urine and feces in the form of metabolites. Approximately 60% of an intravenous radiolabelled dose was recovered in the urine. No unchanged budesonide was detected in the urine.
▧ Half Life :
Following IV administration of budesonide, the elimination half-life is 2.0 to 3.6 hours. This value does not differ between healthy adults and patients with Crohn’s disease.
▧ Clearance :
Plasma clearance, tablet = 0.9 - 1.8 L/min; Systemic clearance, powder, 22R = 1.4 L/min; Systemic clearance, powder, 22S = 1.0 L/min; 0.5 L/min [Athmatic children 4 to 6 years of age]
Độc Tính : Single oral doses of 200 and 400 mg/kg were lethal in female and male mice, respectively. The signs of acute toxicity were decreased motor activity, piloerection and generalized edema.
Chỉ Định : The oral capsule is used for the treatment of mild to moderate active Crohn's disease. The oral tablet is used for induction of remission in patients with active, mild to moderate ulcerative colitis. The oral inhalation formulation is used for the treatment of asthma, non-infectious rhinitis (including hay fever and other allergies), and for treatment and prevention of nasal polyposis.
Tương Tác Thuốc :
  • Bicalutamide CYP3A4 Inhibitors like bicalutamide may increase the serum concentration of budesonide. The clinical significance of this interaction is greater for oral budesonide than for orally inhaled budesonide. Consider reducing the oral budesonide dose when used together with a CYP3A4 inhibitor.
  • Clotrimazole CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of Budesonide (Systemic, Oral Inhalation). Consider reducing the oral budesonide dose when used together with a CYP3A4 inhibitor. This interaction is likely less severe with orally inhaled budesonide. Any patient receiving both budesonide and a moderate CYP3A4 inhibitor should be monitored closely for signs/symptoms of corticosteroid excess.
  • Conivaptan CYP3A4 Inhibitors (Strong) may increase the serum concentration of Budesonide (Systemic, Oral Inhalation). onsider reducing the oral budesonide dose when used together with a strong CYP3A4 inhibitor. This interaction is likely less severe with orally inhaled budesonide. Any patient receiving both budesonide and a strong CYP3A4 inhibitor should be monitored closely for signs/symptoms of corticosteroid excess.
  • Itraconazole Itraconazole may increase levels/effect of budesonide.
  • Ketoconazole Ketoconazole may increase levels/effect of budesonide.
  • Telithromycin Telithromycin may reduce clearance of Budesonide. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Budesonide if Telithromycin is initiated, discontinued or dose changed.
  • Tipranavir Tipranavir may increase the plasma concentration of Budesonide. Monitor for toxic Budesonide effects during concomitant administration.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of budesonide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of budesonide if voriconazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Aerosol, metered - Respiratory (inhalation) - 90 mcg/ACT; 180 mcg/ACT
Capsule, extended release - Oral - 3 mg
Powder, metered - Respiratory (inhalation) - 200 ug
Spray, metered - Nasal - 32 ug
Suspension - Respiratory (inhalation) - 0.25 mg/2 mL; 0.5 mg/2 mL; 1 mg/2 mL
Tablet, extended release - Oral - 9 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Bidien
  • Công ty :
    Sản phẩm biệt dược : Budeson
  • Công ty :
    Sản phẩm biệt dược : Budicort
  • Công ty :
    Sản phẩm biệt dược : ENTOCORT
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Entocort EC
  • Công ty : Eurofarma
    Sản phẩm biệt dược : Noex
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Pulmicort
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Rhinocort
  • Công ty :
    Sản phẩm biệt dược : Rhinosol
  • Công ty :
    Sản phẩm biệt dược : Spirocort
  • Công ty : Santarus
    Sản phẩm biệt dược : Uceris
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01222
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00246
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0093-6815-45
PharmGKB
http://www.pharmgkb.org/drug/PA448681
Wikipedia
http://en.wikipedia.org/wiki/Budesonide
RxList
http://www.rxlist.com/cgi/generic/entocort.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cx1621.shtml
Drugs.com
http://www.drugs.com/cdi/budesonide-spray.html
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