Tìm theo
Etodolac
Các tên gọi khác (11 ) :
  • (+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid
  • (1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid
  • 1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid
  • 1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid
  • 1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic acid
  • Étodolac
  • Etodolac
  • Etodolaco
  • Etodolacum
  • Etodolic acid
  • Etodolsäure
Thuốc giảm đau, hạ sốt, chống viêm không steroid, điều trị Gút và các bệnh xương khớp
Thuốc Gốc
Small Molecule
CAS: 41340-25-4
ATC: M01AB08
ĐG : Actavis Group , http://www.actavis.com
CTHH: C17H21NO3
PTK: 287.3535
Etodolac is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic and antipyretic properties. Its therapeutic effects are due to its ability to inhibit prostaglandin synthesis. It is indicated for relief of signs and symptoms of rheumatoid arthritis and osteoarthritis.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H21NO3
Phân tử khối
287.3535
Monoisotopic mass
287.152143543
InChI
InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
InChI Key
InChIKey=NNYBQONXHNTVIJ-UHFFFAOYSA-N
IUPAC Name
2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
Traditional IUPAC Name
etodolac
SMILES
CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C1
Độ tan chảy
146.5 °C
Độ hòa tan
16 mg/L
logP
2.5
logS
-3.9
pKa (strongest acidic)
4.73
pKa (Strongest Basic)
-4.2
PSA
62.32 Å2
Refractivity
81.16 m3·mol-1
Polarizability
31.94 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
3
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
4.65
Dược Lực Học : Etodolac is an anti-inflammatory agent with analgesic and antipyretic properties. It is used to treat osteoarthritis, rheumatoid arthritis and control acute pain. The therapeutic effects of etodolac are achieved via inhibition of the synthesis of prostaglandins involved in fever, pain, swelling and inflammation. Etodolac is administered as a racemate. As with other NSAIDs, the S-form has been shown to be active while the R-form is inactive. Both enantiomers are stable and there is no evidence of R- to S- conversion in vivo.
Cơ Chế Tác Dụng : Etodolac is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic and antipyretic properties. Its therapeutic effects are due to its ability to inhibit prostaglandin synthesis. It is indicated for relief of signs and symptoms of rheumatoid arthritis and osteoarthritis. Similar to other NSAIDs, the anti-inflammatory effects of etodolac result from inhibition of the enzyme cycooxygenase (COX). This decreases the synthesis of peripheral prostaglandins involved in mediating inflammation. Etodolac binds to the upper portion of the COX enzyme active site and prevents its substrate, arachidonic acid, from entering the active site. Etodolac was previously thought to be a non-selective COX inhibitor, but it is now known to be 5 – 50 times more selective for COX-2 than COX-1. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.
Dược Động Học :
▧ Absorption :
Based on mass balance studies, the systemic bioavailability of etodolac from either the tablet or capsule formulation is at least 80%.
▧ Volume of Distribution :
* 390 mL/kg
▧ Protein binding :
> 99% bound, primarily to albumin
▧ Metabolism :
Etodolac is extensively metabolized in the liver. Renal elimination of etodolac and its metabolites is the primary route of excretion (72%). Metabolites found in urine (with percents of the administered dose) are: unchanged etodolac (1%), etodolac glucuronide (13%), hydroxylated metabolites (6-, 7-, and 8-OH; 5%), hydroxylated metabolite glucuronides (20%), and unidentified metabolites (33%). Fecal excretion accounts for 16% of its elimination.
▧ Route of Elimination :
It is not known whether etodolac is excreted in human milk; however, based on its physical-chemical properties, excretion into breast milk is expected. Etodolac is extensively metabolized in the liver. The hydroxylated-etodolac metabolites undergo further glucuronidation followed by renal excretion and partial elimination in the feces (16% of dose). Approximately 1% of a etodolac dose is excreted unchanged in the urine with 72% of the dose excreted into urine as parent drug plus metabolite.
▧ Half Life :
Terminal t1/2, 7.3 ± 4.0 hours. Distribution t1/2, 0.71 ± 0.50 hours
▧ Clearance :
* Oral cl=49.1 mL/h/kg [Normal healthy adults] * Oral cl=49.4 mL/h/kg [Healthy males (18-65 years)] * Oral cl=35.7 mL/h/kg [Healthy females (27-65 years)] * Oral cl=45.7 mL/h/kg [Eldery (>65 years)] * Oral cl=58.3 mL/h/kg [Renal impairement (46-73 years)] * Oral cl=42.0 mL/h/kg [Hepatic impairement (34-60 years)]
Độc Tính : Selective COX-2 inhibitors have been associated with increased risk of serious cardiovascular events (e.g. myocardial infarction, stroke) in some patients. Current data is insufficient to assess the cardiovascular risk of etodolac. Etodolac may increase blood pressure and/or cause fluid retention and edema. Risk of GI toxicity including bleeding, ulceration and perforation. Risk of direct renal injury, including renal papillary necrosis. Anaphylactoid and serious skin reactions (e.g. exfoliative dermatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis) have been reported. Common adverse events include abdominal pain, constipation, diarrhea, dyspepsia, flatulence, GI bleeding, GI perforation, nausea, peptic ulcer, vomiting, renal function abnormalities, anemia, dizziness, edema, liver function test abnormalities, headache, prolonged bleeding time, pruritus, rash, tinnitus. Symptoms of overdose include lethargy, drowsiness, nausea, vomiting, and epigastric pain.
Chỉ Định : For acute and long-term management of signs and symptoms of osteoarthritis and rheumatoid arthritis, as well as for the management of pain.
Tương Tác Thuốc :
  • Acenocoumarol The NSAID, etodolac, may increase the anticoagulant effect or acenocoumarol.
  • Alendronate Increased risk of gastric toxicity
  • Anisindione The NSAID, etodolac, may increase the anticoagulant effect of anisindione.
  • Azilsartan medoxomil Increases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
  • Colesevelam Bile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
  • Cyclosporine Monitor for nephrotoxicity
  • Dicoumarol The NSAID, etodolac, may increase the anticoagulant effect of dicumarol.
  • Eltrombopag Increases levels of Etodolac via metabolism decrease. UDP-glucuronosyltransferase inhibition.
  • Ginkgo biloba Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
  • Methotrexate The NSAID, etodolac, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
  • Pralatrexate NSAIDs increase the risk of toxicity due to impairment of renal clearance of pralatrexate thus increasing exposure. Monitor for adverse effects or adjust dose of pralatrexate.
  • Timolol The NSAID, Etodolac, may antagonize the antihypertensive effect of Timolol.
  • Trandolapril The NSAID, Etodolac, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Etodolac is initiated, discontinued or dose changed.
  • Treprostinil The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Etodolac. Monitor for increased bleeding during concomitant thearpy.
  • Warfarin The antiplatelet effects of etodolac may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
Liều Lượng & Cách Dùng : Capsule - Oral - 200 mg
Capsule - Oral - 300 mg
Tablet - Oral - 400 mg
Tablet - Oral - 500 mg
Tablet, extended release - Oral - 400 mg
Tablet, extended release - Oral - 500 mg
Tablet, extended release - Oral - 600 mg
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Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00749
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3308
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505184
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00315
ChemSpider
http://www.chemspider.com/Chemical-Structure.3192.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50016799
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0228-2599-11
PharmGKB
http://www.pharmgkb.org/drug/PA449550
Wikipedia
http://en.wikipedia.org/wiki/Etodolac
RxList
http://www.rxlist.com/cgi/generic/etodolac.htm
Drugs.com
http://www.drugs.com/etodolac.html
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