Tìm theo
Erythromycin
Các tên gọi khác (9 ) :
  • (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
  • 3''-O-demethylerythromycin
  • Abomacetin
  • Eritromicina
  • Erythromycin
  • Erythromycin A
  • Erythromycin C
  • Erythromycine
  • Erythromycinum
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 114-07-8
ATC: D10AF02, J01FA01, S01AA17
ĐG : Abbott Laboratories Ltd. , http://www.abbott.com
CTHH: C37H67NO13
PTK: 733.9268
Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus. It inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
Phân tử khối
733.9268
Monoisotopic mass
733.461241235
InChI
InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
InChI Key
InChIKey=ULGZDMOVFRHVEP-RWJQBGPGSA-N
IUPAC Name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
Traditional IUPAC Name
erythromycin
Độ tan chảy
191 °C
Độ hòa tan
2000mg/L at 28°C
logP
3.06
logS
-3.2
pKa (strongest acidic)
12.44
pKa (Strongest Basic)
8.38
PSA
193.91 Å2
Refractivity
186.04 m3·mol-1
Polarizability
78.21 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
13
H Bond Donor Count
5
Physiological Charge
1
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
caco2 Permeability
-5.43
pKa
8.88 (at 25 °C)
Dược Lực Học : Erythromycin is produced by a strain of Streptomyces erythraeus and belongs to the macrolide group of antibiotics. After absorption, erythromycin diffuses readily into most body fluids. In the absence of meningeal inflammation, low concentrations are normally achieved in the spinal fluid, but the passage of the drug across the blood-brain barrier increases in meningitis. Erythromycin is excreted in breast milk. The drug crosses the placental barrier with fetal serum drug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis.
Cơ Chế Tác Dụng : Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus. It inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration. Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or near the “P” or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the “A” or acceptor site to the “P” or donor site is prevented, and subsequent protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by which erythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to the antibacterial activity of the drug.
Dược Động Học :
▧ Absorption :
Orally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topical application of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.
▧ Protein binding :
Erythromycin is largely bound to plasma proteins, ranging from 75 - 95% binding depending on the form.
▧ Metabolism :
Hepatic. Extensively metabolized - after oral administration, less than 5% of the administered dose can be recovered in the active form in the urine. Erythromycin is partially metabolized by CYP3A4 resulting in numerous drug interactions.
▧ Half Life :
0.8 - 3 hours
Độc Tính : Symptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
Chỉ Định : For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases: respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct to antitoxin in infections due to Corynebacterium diphtheriae, in the treatment of infections due to Corynebacterium minutissimum, intestinal amebiasis caused by Entamoeba histolytica, acute pelvic inflammatory disease caused by Neisseria gonorrhoeae, skin and soft tissue infections of mild to moderate severity caused by Streptococcus pyogenes and Staphylococcus aureus, primary syphilis caused by Treponema pallidum, infections caused by Chlamydia trachomatis, nongonococcal urethritis caused by Ureaplasma urealyticum, and Legionnaires' disease caused by Legionella pneumophila.
Tương Tác Thuốc :
  • Acenocoumarol The macrolide, erythromycin, may increase the anticoagulant effect of acenocoumarol.
  • Alfentanil The macrolide, erythromycin, may increase the effect and toxicity of alfentanil.
  • Alprazolam The macrolide, erythromycin, may increase the effect of the benzodiazepine, alprazolam.
  • Aminophylline The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, aminophylline.
  • Amiodarone Increased risk of cardiotoxicity and arrhythmias
  • Anisindione The macrolide, erythromycin, may increase the anticoagulant effect of anisindione.
  • Aprepitant Erythromycin, a moderate CYP3A4 inhibitor, may increase the effect and toxicity of aprepitant.
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Astemizole Increased risk of cardiotoxicity and arrhythmias
  • Atorvastatin The macrolide, erythromycin, may increase the toxicity of the statin, atorvastatin.
  • Avanafil Co-administration with the moderate CYP3A4 inhibitor erythromycin resulted in an approximate 3.6-fold increase in AUC0-inf and 2.0-fold increase in Cmax of avanafil.
  • Bendamustine Decreases metabolism, thus decreasing the effects of bendamustine.
  • Bretylium Increased risk of cardiotoxicity and arryhthmias
  • Bromazepam Erythromcyin may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if erythromycin is initiated, discontinued or dose changed. Dosage adjustments may be required.
  • Bromocriptine Erythromycin increases serum levels of bromocriptine
  • Buspirone The macrolide, erythromycin, may increase the effect and toxicity of buspirone.
  • Cabergoline Erythromycin increases serum levels and toxicity of cabergoline
  • Carbamazepine The macrolide, erythromycin, may increase the effect of carbamazepine.
  • Cerivastatin The macrolide, erythromycin, may increase the toxicity of the statin, cerivastatin.
  • Cilostazol Erythromycin increases the effect of cilostazol
  • Cinacalcet The macrolide, erythromycin, may increase the serum concentration and toxicity of cinacalcet.
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Citalopram Possible serotoninergic syndrome with this combination
  • Clozapine Erythromycin increases the effect of clozapine
  • Colchicine Severe colchicine toxicity can occur
  • Cyclosporine The macrolide, erythromycin, may increase the effect of cyclosporine.
  • Diazepam The macrolide, erythromycin, may increase the effect of the benzodiazepine, diazepam.
  • Dicoumarol The macrolide, erythromycin, may increase the anticoagulant effect of dicumarol..
  • Digoxin The macrolide, erythromycin, may increase the effect of digoxin in 10% of patients.
  • Dihydroergotamine Possible ergotism and severe ischemia with this combination
  • Disopyramide Increased risk of cardiotoxicity and arrhythmias
  • Docetaxel Erythromycin may increase the serum levels and toxicity of docetaxel.
  • Dofetilide Increased risk of cardiotoxicity and arrhythmias
  • Dyphylline The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, dyphylline.
  • Eletriptan The macrolide, erythromycin, may increase the effect and toxicity of eletriptan.
  • Eltrombopag Affects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.
  • Eplerenone This CYP3A4 inhibitor increases the effect and toxicity of eplerenone
  • Ergonovine Possible ergotism and severe ischemia with this combination
  • Ergotamine Possible ergotism and severe ischemia with this combination
  • Erlotinib This CYP3A4 inhibitor increases levels/toxicity of erlotinib
  • Everolimus The macrolide, erythromycin, may increase the serum concentration and toxicity of everolimus.
  • Felodipine Erythromycin increases the effect of felodipine
  • Fluoxetine Possible serotoninergic syndrome with this combination
  • Gefitinib This CYP3A4 inhibitor increases levels/toxicity of gefitinib
  • Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
  • Imatinib The macrolide, erythromycin, may increase the serum concentration of imatinib.
  • Indacaterol Strong inhibitors of CYP3A4 may increase levels of indacaterol. Monitor closely for adverse events.
  • Itraconazole The macrolide, erythromycin, may increase the effect and toxicity of itraconazole.
  • Ivacaftor Moderate CYP3A4 inhibitors may increase levels of ivacaftor. Consider dose reduction.
  • Levofloxacin Increased risk of cardiotoxicity and arrhythmias
  • Lincomycin Possible antagonism of action with this combination.
  • Lovastatin The macrolide, erythromycin, may increase the toxicity of the statin, lovastatin.
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Methylergometrine Possible ergotism and severe ischemia with this combination
  • Methylprednisolone The macrolide, erythromycin, may increase the effect of corticosteroid, methylprednisolone.
  • Methysergide Possible ergotism and severe ischemia with this combination
  • Midazolam The macrolide, erythromycin, may increase the effect of the benzodiazepine, midazolam.
  • Moxifloxacin Increased risk of cardiotoxicity and arrhythmias
  • Oxtriphylline The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, oxtriphylline.
  • Pazopanib Affects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib. Consider alternate therapy.
  • Pimozide Increased risk of cardiotoxicity and arrhythmias
  • Pitavastatin Erythromycin decreases metabolism of pitavastatin. Do not exceed 1 mg per day of pitavastatin or use alternative therapy.
  • Quetiapine The macrolide, erythromycin, may increase the effect and toxicity of quetiapine.
  • Quinidine Increased risk of cardiotoxicity and arrhythmias
  • Quinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
  • Quinupristin This combination presents an increased risk of toxicity
  • Ranolazine Increased levels of ranolazine - risk of toxicity
  • Repaglinide The macrolide, erythromycin, may increase the effect of repaglinide.
  • Rifabutin The rifamycin, rifabutin, may decrease the effect of the macrolide, erythromycin.
  • Rifampicin The rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.
  • Ritonavir Increased toxicity of both agents
  • Roflumilast Increases roflumilast levels.
  • Saxagliptin Erythromycin is an inhibitor of CYP3A4 which increases exposure of saxagliptin. Decrease dose of saxagliptin to 2.5 mg per day.
  • Sertraline Possible serotoninergic syndrome with this combination
  • Sibutramine Erythromycin increases the effect and toxicity of sibutramine
  • Sildenafil The macrolide, erythromycin, may increase the effect and toxicity of sildenafil.
  • Silodosin Erythromycin is a moderate inhibitor of CYP3A4 and inhibits P-glycoprotein thus increasing the potential for adverse effects
  • Simvastatin The macrolide, erythromycin, may increase the toxicity of the statin, simvastatin.
  • Sirolimus The macrolide, erythromycin, may increase the serum concentration of sirolimus.
  • Sotalol Increased risk of cardiotoxicity and arrhythmias
  • Sparfloxacin Increased risk of cardiotoxicity and arrhythmias
  • Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolide antibiotic, erythromycin, may also increase the blood concentration of tacrolimus.
  • Tamsulosin Erythromycin, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Erythromycin is initiated, discontinued, or dose changed.
  • Telithromycin Telithromycin may reduce clearance of Erythromycin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Erythromycin if Telithromycin is initiated, discontinued or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Theophylline The macrolide, erythromycin, may increase the effect and toxicity of theophylline.
  • Thioridazine Increased risk of cardiotoxicity and arrhythmias
  • Thiothixene May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
  • Tolvaptan Erythromycin is a moderate inhibitor of CYP3A4 and will considerably increase tolvaptan serum concentrations
  • Topotecan The p-glycoprotein inhibitor, Erythromycin, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
  • Toremifene Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
  • Tramadol Erythromycin may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
  • Trazodone The CYP3A4 inhibitor, Erythromycin , may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Erythromycin is initiated, discontinued or dose changed.
  • Triazolam The macrolide, erythromycin, may increase the effect of the benzodiazepine, triazolam.
  • Trimipramine Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Valproic Acid The macrolide antibiotic, Erythromycin, may increase the serum concentratin of Valproic acid. Consider alternate therapy or monitor for changes in Valproic acid therapeutic and adverse effects if Erythromycin is initiated, discontinued or dose changed.
  • Vardenafil Erythromycin, a moderate CYP3A4 inhibitor, may reduce the metabolism and clearance of vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of vardenafil if erythromycin is initiated, discontinued or dose changed.
  • Verapamil Erythromycin, a moderate CYP3A4 inhibitor, may increase the serum concentration of veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of verapamil if erythromycin is initiated, discontinued or dose changed.
  • Vinblastine Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the vinblastine serum concentration and distribution in certain cells. Consider alternate therapy to avoid vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of vinblastine if erythromycin is initiated, discontinued or dose changed.
  • Vincristine Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vincristine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Erythromycin is initiated, discontinued or dose changed.
  • Vinorelbine Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinorelbine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Erythromycin is initiated, discontinued or dose changed.
  • Vismodegib P-glycoprotein inhibitors may increase the chance of adverse drug reactions.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of erythromycin by decreasing its metabolism. Erythromycin may increase the serum concentration of voriconazole by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose changed.
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Warfarin The macrolide, erythromycin, may increase the anticoagulant effect of warfarin.
  • Zafirlukast Erythromycin may decrease the serum concentration and effect of zafirlukast.
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
  • Zopiclone The macrolide antibiotic, erythromycin, may increase the serum concentration of zopiclone. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if erythromycin is initiated, discontinued or dose changed.
  • Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Liều Lượng & Cách Dùng : Capsule, coated - Oral
Liquid - Dental
Liquid - Oral
Ointment - Ophthalmic
Powder - Intravenous
Powder - Oral
Powder, for solution - Intravenous
Powder, for solution - Oral
Powder, for suspension - Oral
Suspension - Oral
Tablet - Oral
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