Peringatan Keamanan

Blurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating

Esomeprazole

DB00736

small molecule approved investigational

Deskripsi

Esomeprazole, sold under the brand name Nexium, is a proton pump inhibitor (PPI) medication used for the management of gastroesophageal reflux disease (GERD), for gastric protection to prevent recurrence of stomach ulcers or gastric damage from chronic use of NSAIDs, and for the treatment of pathological hypersecretory conditions including Zollinger-Ellison (ZE) Syndrome. It can also be found in quadruple regimens for the treatment of H. pylori infections along with other antibiotics including DB01060, DB01211, and DB00916, for example.A177271, F4498 Its efficacy is considered similar to other medications within the PPI class including DB00338, DB00213, DB00448, DB05351, and DB01129. Esomeprazole is the s-isomer of DB00338, which is a racemate of the S- and R-enantiomer. Esomeprazole has been shown to inhibit acid secretion to a similar extent as DB00338, without any significant differences between the two compounds in vitro.

Esomeprazole exerts its stomach acid-suppressing effects by preventing the final step in gastric acid production by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cells. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. As the binding of esomeprazole to the (H+, K+)-ATPase enzyme is irreversible and new enzyme needs to be expressed in order to resume acid secretion, esomeprazole's duration of antisecretory effect persists longer than 24 hours.FDA Label

PPIs such as esomeprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes.A177577, A177580

Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as esomeprazole has been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients such as iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.A177571

Rapid discontinuation of PPIs such as esomeprazole may cause a rebound effect and a short term increase in hypersecretion.A177574 Esomeprazole doses should be slowly lowered, or tapered, before discontinuing to prevent this rebound effect.

Struktur Molekul 2D

Berat 345.416
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) 1-1.5 hours
Volume Distribusi The apparent volume of distribution at steady state in healthy volunteers is approximately 16 L.[FDA Label]
Klirens (Clearance) -

Absorpsi

After oral administration, peak plasma levels (Cmax) occur at approximately 1.5 hours (Tmax). The Cmax increases proportionally when the dose is increased, and there is a three-fold increase in the area under the plasma concentration-time curve (AUC) from 20 to 40 mg. At repeated once-daily dosing with 40 mg, the systemic bioavailability is approximately 90% compared to 64% after a single dose of 40 mg. The mean exposure (AUC) to esomeprazole increases from 4.32 ?mol*hr/L on Day 1 to 11.2 ?mol*hr/L on Day 5 after 40 mg once daily dosing. The AUC after administration of a single 40 mg dose of Esomeprazole is decreased by 43% to 53% after food intake compared to fasting conditions. Esomeprazole should be taken at least one hour before meals.FDA Label Combination Therapy with Antimicrobials: Esomeprazole magnesium 40 mg once daily was given in combination with DB01211 500 mg twice daily and DB01060 1000 mg twice daily for 7 days to 17 healthy male and female subjects. The mean steady state AUC and Cmax of esomeprazole increased by 70% and 18%, respectively during triple combination therapy compared to treatment with esomeprazole alone. The observed increase in esomeprazole exposure during co-administration with clarithromycin and amoxicillin is not expected to produce significant safety concerns.

Metabolisme

Esomeprazole is extensively metabolized in the liver by the cytochrome P450 (CYP) enzyme system. The metabolites of esomeprazole lack antisecretory activity. The major part of esomeprazole’s metabolism is dependent upon the CYP2C19 isoenzyme, which forms the hydroxy and desmethyl metabolites. The remaining amount is dependent on CYP3A4 which forms the sulphone metabolite. CYP2C19 isoenzyme exhibits polymorphism in the metabolism of esomeprazole, since some 3% of Caucasians and 15 to 20% of Asians lack CYP2C19 and are termed Poor Metabolizers.FDA Label However, the influence of CYP 2C19 polymorphism is less pronounced for esomeprazole than for omeprazole.F4495 At steady state, the ratio of AUC in Poor Metabolizers to AUC in the rest of the population (Extensive Metabolizers) is approximately 2. Following administration of equimolar doses, the S- and R-isomers are metabolized differently by the liver, resulting in higher plasma levels of the S- than of the R-isomer.FDA Label Nine major urinary metabolites have been detected. The two main metabolites have been identified as hydroxyesomeprazole and the corresponding carboxylic acid. Three major metabolites have been identified in plasma: the 5-O-desmethyl- and sulphone derivatives and hydroxyesomeprazole. The major metabolites of esomeprazole have no effect on gastric acid secretion.F4495

Rute Eliminasi

The plasma elimination half-life of esomeprazole is approximately 1 to 1.5 hours. Less than 1% of parent drug is excreted in the urine. Approximately 80% of an oral dose of esomeprazole is excreted as inactive metabolites in the urine, and the remainder is found as inactive metabolites in the feces.

Farmakogenomik

2 Varian
CYP2C19 (rs4244285)

Patients with this genotype have reduced metabolism of esomeprazole.

CYP2C19 (rs4986893)

Patients with this genotype have reduced metabolism of esomeprazole.

Interaksi Makanan

1 Data
  • 1. Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.

Interaksi Obat

400 Data
Cyclosporine The serum concentration of Cyclosporine can be increased when it is combined with Esomeprazole.
Cilostazol The serum concentration of Cilostazol can be increased when it is combined with Esomeprazole.
Dabrafenib The serum concentration of Esomeprazole can be decreased when it is combined with Dabrafenib.
Amphetamine Esomeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
Atazanavir Esomeprazole can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
Bosutinib Esomeprazole can cause a decrease in the absorption of Bosutinib resulting in a reduced serum concentration and potentially a decrease in efficacy.
Cefditoren The serum concentration of Cefditoren can be decreased when it is combined with Esomeprazole.
Dabigatran etexilate Esomeprazole can cause a decrease in the absorption of Dabigatran etexilate resulting in a reduced serum concentration and potentially a decrease in efficacy.
Dasatinib Esomeprazole can cause a decrease in the absorption of Dasatinib resulting in a reduced serum concentration and potentially a decrease in efficacy.
Delavirdine Esomeprazole can cause a decrease in the absorption of Delavirdine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Dextroamphetamine Esomeprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
Erlotinib Esomeprazole can cause a decrease in the absorption of Erlotinib resulting in a reduced serum concentration and potentially a decrease in efficacy.
Fluconazole The metabolism of Esomeprazole can be decreased when combined with Fluconazole.
Gefitinib Esomeprazole can cause a decrease in the absorption of Gefitinib resulting in a reduced serum concentration and potentially a decrease in efficacy.
Indinavir Esomeprazole can cause a decrease in the absorption of Indinavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
Itraconazole Esomeprazole can cause a decrease in the absorption of Itraconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
Ledipasvir Esomeprazole can cause a decrease in the absorption of Ledipasvir resulting in a reduced serum concentration and potentially a decrease in efficacy.
Methylphenidate Esomeprazole can cause an increase in the absorption of Methylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.
Dexmethylphenidate Esomeprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.
Nelfinavir The serum concentration of Nelfinavir can be decreased when it is combined with Esomeprazole.
Nilotinib The serum concentration of Nilotinib can be decreased when it is combined with Esomeprazole.
Pazopanib Esomeprazole can cause a decrease in the absorption of Pazopanib resulting in a reduced serum concentration and potentially a decrease in efficacy.
Posaconazole Esomeprazole can cause a decrease in the absorption of Posaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
Raltegravir Esomeprazole can cause an increase in the absorption of Raltegravir resulting in an increased serum concentration and potentially a worsening of adverse effects.
Rilpivirine Esomeprazole can cause a decrease in the absorption of Rilpivirine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Riociguat Esomeprazole can cause a decrease in the absorption of Riociguat resulting in a reduced serum concentration and potentially a decrease in efficacy.
Risedronic acid Esomeprazole can cause an increase in the absorption of Risedronic acid resulting in an increased serum concentration and potentially a worsening of adverse effects.
Saquinavir The serum concentration of Saquinavir can be increased when it is combined with Esomeprazole.
Tipranavir The metabolism of Esomeprazole can be increased when combined with Tipranavir.
Voriconazole The metabolism of Esomeprazole can be decreased when combined with Voriconazole.
Luliconazole The serum concentration of Esomeprazole can be increased when it is combined with Luliconazole.
Phenytoin The serum concentration of Phenytoin can be increased when it is combined with Esomeprazole.
Fosphenytoin The serum concentration of Fosphenytoin can be increased when it is combined with Esomeprazole.
Escitalopram The serum concentration of Escitalopram can be increased when it is combined with Esomeprazole.
Succinic acid The excretion of Succinic acid can be decreased when combined with Esomeprazole.
Citrulline The excretion of Citrulline can be decreased when combined with Esomeprazole.
Oseltamivir The excretion of Oseltamivir can be decreased when combined with Esomeprazole.
Cefotiam The excretion of Cefotiam can be decreased when combined with Esomeprazole.
Piperacillin The excretion of Piperacillin can be decreased when combined with Esomeprazole.
Aminohippuric acid The excretion of Aminohippuric acid can be decreased when combined with Esomeprazole.
Trifluridine The excretion of Trifluridine can be decreased when combined with Esomeprazole.
Allopurinol The excretion of Allopurinol can be decreased when combined with Esomeprazole.
Cefdinir The excretion of Cefdinir can be decreased when combined with Esomeprazole.
Cephalexin The excretion of Cephalexin can be decreased when combined with Esomeprazole.
Valaciclovir The excretion of Valaciclovir can be decreased when combined with Esomeprazole.
Levocarnitine The excretion of Levocarnitine can be decreased when combined with Esomeprazole.
Leucovorin The excretion of Leucovorin can be decreased when combined with Esomeprazole.
Fluorescein The excretion of Fluorescein can be decreased when combined with Esomeprazole.
Acyclovir The excretion of Acyclovir can be decreased when combined with Esomeprazole.
Cefaclor The excretion of Cefaclor can be decreased when combined with Esomeprazole.
Quinapril The excretion of Quinapril can be decreased when combined with Esomeprazole.
Bumetanide The excretion of Bumetanide can be decreased when combined with Esomeprazole.
Dinoprostone The excretion of Dinoprostone can be decreased when combined with Esomeprazole.
Famotidine The excretion of Famotidine can be decreased when combined with Esomeprazole.
Benzylpenicillin The excretion of Benzylpenicillin can be decreased when combined with Esomeprazole.
Rosuvastatin The excretion of Rosuvastatin can be decreased when combined with Esomeprazole.
Cefazolin The excretion of Cefazolin can be decreased when combined with Esomeprazole.
Ceftizoxime The excretion of Ceftizoxime can be decreased when combined with Esomeprazole.
Cefacetrile The excretion of Cefacetrile can be decreased when combined with Esomeprazole.
Ceftibuten The excretion of Ceftibuten can be decreased when combined with Esomeprazole.
Tazobactam The excretion of Tazobactam can be decreased when combined with Esomeprazole.
Cyclic adenosine monophosphate The excretion of Cyclic adenosine monophosphate can be decreased when combined with Esomeprazole.
Cholic Acid The excretion of Cholic Acid can be decreased when combined with Esomeprazole.
Glutaric Acid The excretion of Glutaric Acid can be decreased when combined with Esomeprazole.
Oxalic Acid The excretion of Oxalic Acid can be decreased when combined with Esomeprazole.
Doripenem The excretion of Doripenem can be decreased when combined with Esomeprazole.
Saxagliptin The excretion of Saxagliptin can be decreased when combined with Esomeprazole.
Ellagic acid The excretion of Ellagic acid can be decreased when combined with Esomeprazole.
Cefaloridine The excretion of Cefaloridine can be decreased when combined with Esomeprazole.
Avibactam The excretion of Avibactam can be decreased when combined with Esomeprazole.
Eluxadoline The excretion of Eluxadoline can be decreased when combined with Esomeprazole.
Silibinin The excretion of Silibinin can be decreased when combined with Esomeprazole.
Relebactam The excretion of Relebactam can be decreased when combined with Esomeprazole.
Hydrochlorothiazide The excretion of Hydrochlorothiazide can be decreased when combined with Esomeprazole.
Conjugated estrogens The excretion of Conjugated estrogens can be decreased when combined with Esomeprazole.
Indomethacin The excretion of Indomethacin can be decreased when combined with Esomeprazole.
Zidovudine The excretion of Zidovudine can be decreased when combined with Esomeprazole.
Cimetidine The excretion of Cimetidine can be decreased when combined with Esomeprazole.
Hydrocortisone The excretion of Hydrocortisone can be decreased when combined with Esomeprazole.
Tetracycline The excretion of Tetracycline can be decreased when combined with Esomeprazole.
Estradiol The excretion of Estradiol can be decreased when combined with Esomeprazole.
Ranitidine The excretion of Ranitidine can be decreased when combined with Esomeprazole.
Tenofovir alafenamide The excretion of Tenofovir alafenamide can be decreased when combined with Esomeprazole.
Pravastatin The excretion of Pravastatin can be decreased when combined with Esomeprazole.
Tenofovir disoproxil The excretion of Tenofovir disoproxil can be decreased when combined with Esomeprazole.
Fexofenadine The excretion of Fexofenadine can be decreased when combined with Esomeprazole.
Sitagliptin The excretion of Sitagliptin can be decreased when combined with Esomeprazole.
Taurocholic acid The excretion of Taurocholic acid can be decreased when combined with Esomeprazole.
Baricitinib The serum concentration of Baricitinib can be increased when it is combined with Esomeprazole.
Tenofovir The excretion of Tenofovir can be decreased when combined with Esomeprazole.
Oxytetracycline The excretion of Oxytetracycline can be decreased when combined with Esomeprazole.
Polythiazide The excretion of Polythiazide can be decreased when combined with Esomeprazole.
Prednisolone phosphate The excretion of Prednisolone phosphate can be decreased when combined with Esomeprazole.
Dexamethasone acetate The excretion of Dexamethasone acetate can be decreased when combined with Esomeprazole.
Levothyroxine Esomeprazole can cause a decrease in the absorption of Levothyroxine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Bisacodyl The therapeutic efficacy of Bisacodyl can be decreased when used in combination with Esomeprazole.
Captopril Esomeprazole can cause a decrease in the absorption of Captopril resulting in a reduced serum concentration and potentially a decrease in efficacy.
Cefuroxime The serum concentration of Cefuroxime can be decreased when it is combined with Esomeprazole.
Memantine Esomeprazole may decrease the excretion rate of Memantine which could result in a higher serum level.
Sulpiride The therapeutic efficacy of Sulpiride can be increased when used in combination with Esomeprazole.

Target Protein

Potassium-transporting ATPase alpha chain 1 ATP4A
Potassium-transporting ATPase subunit beta ATP4B
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 DDAH1

Referensi & Sumber

Synthesis reference: Manne Reddy, "Amorphous hydrates of esomeprazole magnesium and process for the preparation thereof." U.S. Patent US20040167173, issued August 26, 2004.
Artikel (PubMed)
  • PMID: 10886041
    Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7.
  • PMID: 16961157
    Klotz U: Clinical impact of CYP2C19 polymorphism on the action of proton pump inhibitors: a review of a special problem. Int J Clin Pharmacol Ther. 2006 Jul;44(7):297-302.
  • PMID: 23825361
    Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3.
  • PMID: 28588208
    Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1.
  • PMID: 29658189
    Haastrup PF, Thompson W, Sondergaard J, Jarbol DE: Side Effects of Long-Term Proton Pump Inhibitor Use: A Review. Basic Clin Pharmacol Toxicol. 2018 Aug;123(2):114-121. doi: 10.1111/bcpt.13023. Epub 2018 May 24.
  • PMID: 19362552
    Reimer C, Sondergaard B, Hilsted L, Bytzer P: Proton-pump inhibitor therapy induces acid-related symptoms in healthy volunteers after withdrawal of therapy. Gastroenterology. 2009 Jul;137(1):80-7, 87.e1. doi: 10.1053/j.gastro.2009.03.058. Epub 2009 Apr 10.
  • PMID: 27102658
    Fallone CA, Chiba N, van Zanten SV, Fischbach L, Gisbert JP, Hunt RH, Jones NL, Render C, Leontiadis GI, Moayyedi P, Marshall JK: The Toronto Consensus for the Treatment of Helicobacter pylori Infection in Adults. Gastroenterology. 2016 Jul;151(1):51-69.e14. doi: 10.1053/j.gastro.2016.04.006. Epub 2016 Apr 19.

Contoh Produk & Brand

Produk: 473 • International brands: 22
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    Kit • - • Oral; Topical • US • Generic • Approved
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Menampilkan 8 dari 473 produk.
International Brands
  • Alenia — Delta
  • Awa-Block — Usawa
  • Axagon — Simesa
  • Cor — Prater
  • Cronopep — Biotoscana
  • Emanera — Krka
  • Emep — Aristopharma
  • Emozul — HYGIA
  • ES-OD — Piramal Healthcare
  • Esmep — HYGIA

Sekuens Gen/Protein (FASTA)

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