Tìm theo
Omeprazole
Các tên gọi khác (4 ) :
  • OMEP
  • OMP
  • OMZ
  • Prilosec
Thuốc đường tiêu hóa
Thuốc Gốc
Small Molecule
CAS: 73590-58-6
ATC: A02BC01, A02BC05
ĐG : Aidarex Pharmacuticals LLC , http://www.aidarex.com
CTHH: C17H19N3O3S
PTK: 345.416
A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and Zollinger-Ellison syndrome. Omeprazole belongs to a class of antisecretory compounds, the substituted benzimidazoles, that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase enzyme system at the secretory surface of the gastric parietal cell.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H19N3O3S
Phân tử khối
345.416
Monoisotopic mass
345.114712179
InChI
InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
InChI Key
InChIKey=SUBDBMMJDZJVOS-UHFFFAOYSA-N
IUPAC Name
6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methane]sulfinyl}-1H-1,3-benzodiazole
Traditional IUPAC Name
5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-3H-1,3-benzodiazole
SMILES
COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C
Độ tan chảy
155 °C
Độ hòa tan
Very slightly soluble
logP
2.23
logS
-3
pKa (strongest acidic)
9.29
pKa (Strongest Basic)
4.77
PSA
77.1 Å2
Refractivity
93.66 m3·mol-1
Polarizability
37.45 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
5
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : After oral administration, the onset of the anti-secretory effect of omeprazole occurs within one hour and maximum effect occurring within two hours. At 24 hours, inhibition of secretion is approximately 50% of maximum and duration of inhibition lasts up to 72 hours. Although omeprazole has a very short plasma half-life, the anti-secretory effect lasts for a long time due to prolonged binding to parietal H+/K+ ATPase enzyme. When the drug has been discontinued, secretory activity will return to baseline over 3-5 days. The inhibitory effect of omeprazole on acid secretion increases with repeated once-daily dosing, reaching a plateau after four days. In studies involving more than 200 patients, serum gastrin levels increased during the first 1 to 2 weeks of once-daily administration of therapeutic doses of omeprazole in parallel with inhibition of acid secretion. Systemic effects of omeprazole in the CNS, cardiovascular and respiratory systems have not been found to date.
Cơ Chế Tác Dụng : A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and Zollinger-Ellison syndrome. Omeprazole belongs to a class of antisecretory compounds, the substituted benzimidazoles, that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase enzyme system at the secretory surface of the gastric parietal cell. Omeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, omeprazole blocks the final step in acid production, thus reducing gastric acidity.
Dược Động Học :
▧ Absorption :
The delayed-release capsule are enteric-coated (as omeprazole is acid-labile) so the absorption of omprazole begins once the granules leave the stomach. Absorption is rapid. Peak plasma levels occur within 0.5 - 3.5 hours. The absolute bioavailability (compared with intravenous administration) of the delayed-release capsule is 30-40% at doses of 20 - 40 mg, due to presystemic metabolism. This value increases slightly when given repeatedly. Based on a relative bioavailability study, the AUC and Cmax of PRILOSEC (omeprazole magnesium) for Delayed-Release Oral Suspension were 87% and 88% of those for PRILOSEC Delayed-Release Capsules, respectively. Interestingly, when the 40 mg delayed release capsule is given with or without applesauce, it is bioequivalent. However, when the 20 mg delayed release capsule is given with the same conditions, it is not bioequivalent. When the same capsule is given to the elderly, bioavailability increases. Omeprazole was 76% bioavailable.
▧ Protein binding :
95% bound to human plasma protein.
▧ Metabolism :
Hepatic. Omeprazole is extensively metabolized by the cytochrome P450 (CYP) enzyme system. The two primary CYP isozymes involved are CYP2C19 and CYP3A4. Metabolism is stereoselective in which the S-isomer is converted to 5'O-desmethylomeprazole via CYP2C19. CYP3A4 converts the S-isomer to 3-hydroxyomeprazole. The R-isomer is converted to 5-hydroxyomeprazole by CYP2C19. CYP3A4 converts the R-isomer to any four different metabolites: 5-hydroxyomeprazole (5-OH OME), omeprazole sulfone (OME sulfone), 5'-O-desmethylomeprazole (5'-desmethyl OME), and 3-hydroxyomeprazole (3-OH OME).
▧ Route of Elimination :
Urinary excretion is a primary route of excretion of omeprazole metabolites. Little, if any unchanged drug was excreted in the urine. The majority of the dose (about 77%) was eliminated in urine as at least six metabolites. Two were identified as hydroxyomeprazole and the corresponding carboxylic acid. The remainder of the dose was recovered in the feces.
▧ Half Life :
0.5-1 hour (healthy subjects, delayed-release capsule); 3 hours (hepatic impairment)
▧ Clearance :
* 500 - 600 mL/min [Total body clearance, healthy subjects, delayed-release capsule] * 250 mL/min [Plasma clearance, Geriatric] * 70 mL/min [Plasma clearance, Hepatic Impairment]
Độc Tính : Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.
Chỉ Định : Omeprazole is indicated for the treatment of duodenal ulcers, benign gastric ulcers, gastroesophageal reflux disease (GERD), heartburn and other symptoms associated with GERD, erosive esophagitis, and long-term treatment of pathological hypersecretory conditions like Zollinger-Ellison syndrome, multiple endocrine adenomas, and systemic mastocytosis.
Tương Tác Thuốc :
  • Alprazolam Omeprazole may increase the effect of the benzodiazepine, alprazolam.
  • Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
  • Avanafil Nineteen healthy male volunteers received a single 40 omeprazole delayed-release capsule once daily for 8 days (Days 1-8), and a single 200 mg avanafil on Day 8. Twelve hour pharmacokinetics of omeprazole on Days 7 and 8 were compared. Co-administration with avanafil resulted in an approximate 5.9% increase in AUC0-inf and 8.6% increase in Cmax of omeprazole.
  • Bendamustine Affects hepatic CYP1A2 metabolism, thus increasing bendamustine levels. Concentration of active metabolites may be decreased due to decreased conversion.
  • Cefditoren Proton pump inhibitors such as omeprazole may decrease the serum concentration of cefditoren. If possible, avoid use of cefditoren with proton pump inhibitors (PPIs). Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of PPIs can not be avoided.
  • Chlordiazepoxide Omeprazole may increase the effect of the benzodiazepine, chlordiazepoxide.
  • Cilostazol Omeprazole increases the effect of cilostazol
  • Clonazepam Omeprazole may increase the effect of the benzodiazepine, clonazepam.
  • Clopidogrel Omeprazole may decrease serum concentrations of the active metabolite(s) of clopidogrel. Clopidogrel prescribing information recommends avoiding concurrent use with omeprazole, due to the possibility that combined use may result in decreased clopidogrel effectiveness.
  • Clorazepate Omeprazole may increase the effect of the benzodiazepine, clorazepate.
  • Cyclosporine Omeprazole increases the effect and toxicity of cyclosporine
  • Dasatinib Omeprazole may decrease the serum level of dasatinib.
  • Diazepam Omeprazole may increase the effect of the benzodiazepine, diazepam.
  • Disopyramide The beta-blocker increases toxicity of disopyramide
  • Enoxacin Omeprazole may decrease the absorption of enoxacin.
  • Estazolam Omeprazole may increase the effect of the benzodiazepine, estazolam.
  • Ethotoin Omeprazole increases the effect of hydantoin
  • Flurazepam Omeprazole may increase the effect of the benzodiazepine, flurazepam.
  • Fosphenytoin Omeprazole increases the effect of hydantoin
  • Halazepam Omeprazole may increase the effect of the benzodiazepine, halazepam.
  • Indinavir Omeprazole decreases the absorption of indinavir
  • Itraconazole The proton pump inhibitor, omeprazole, may decrease the absorption of itraconazole.
  • Ketazolam Omeprazole may increase the effect of the benzodiazepine, ketazolam.
  • Ketoconazole The proton pump inhibitor, omeprazole, may decrease the absorption of ketoconazole.
  • Mephenytoin Omeprazole increases the effect of hydantoin
  • Methotrexate Omeprazole increases the levels of methotrexate
  • Midazolam Omeprazole may increase the effect of the benzodiazepine, midazolam.
  • Ospemifene Moderate CYP2C19 inhibitors may increase levels of ospemifene. Monitor concomitant therapy closely.
  • Phenytoin Omeprazole increases the effect of hydantoin
  • Prazepam Omeprazole may increase the effect of the benzodiazepine, prazepam.
  • Quazepam Omeprazole may increase the effect of the benzodiazepine, quazepam.
  • Rilpivirine Proton-pump inhibitors increase gastric pH which causes a decrease in the exposure of rilpivirine thus reducing efficacy.
  • Roflumilast Affects CYP1A2 metabolism; decreases level or effect of roflumilast.
  • St. John's Wort St. John's Wort decreases the levels/effects of omeprazole
  • Tacrolimus Omeprazole may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Omeprazole therapy is initiated, discontinued or altered.
  • Tipranavir Tipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Omeprazole. Consider alternate therapy or increase the dose of Omeprazole based on the therapeutic response.
  • Tocilizumab Omeprazole is a CYP2C19 and CYP3A4 substrate. Exposure of omeprazole decreases following administration of tocilizumab..
  • Triazolam Omeprazole may increase the effect of the benzodiazepine, triazolam.
  • Trimipramine The strong CYP2C19 inhibitor, Omeprazole, may decrease the metabolism and clearance of Trimipramine, a CYP2C19 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Omeprazole is initiated, discontinued or dose changed.
  • Vismodegib Vismodegib serum concentrations may be decreased by proton pump inhibitors such as omeprazole.
  • Voriconazole Voriconazole increases the effect and toxicity of omeprazole
Liều Lượng & Cách Dùng : Capsule, delayed release - Oral - 10 mg, 20 mg, 40 mg
Suspension - Oral - 2 mg/mL
Tablet, delayed release - Oral - 20 mg
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Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00338
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4594
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46509065
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07324
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00455
ChemSpider
http://www.chemspider.com/Chemical-Structure.4433.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50241343
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/63739-358-10
PharmGKB
http://www.pharmgkb.org/drug/PA450704
Wikipedia
http://en.wikipedia.org/wiki/Omeprazole
RxList
http://www.rxlist.com/cgi/generic/omepra.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pri1350.shtml
Drugs.com
http://www.drugs.com/omeprazole.html
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