Abboticin;Abomacetin;Ak-mycin;Akne-Mycin;Aknin;Benzamycin;Benzamycin Pak;Bristamycin;Dotycin;Dumotrycin;E-Base;E-Glades;E-Mycin;E-Solve 2;Emgel;EMU;Eritrocina;Ermycin;Ery-Sol;Ery-Tab;Eryc;Eryc 125;Eryc Sprinkles;Erycen;Erycette;Erycin;Erycinum;Eryderm;Erygel;Erymax;Erypar;Erythra-Derm;Erythro;Erythro-Statin;Erythrogran;Erythroguent;Erythromast 36;Erythromid;Erythromycin A;Erythromycin B;Ethril 250;ETS;Ilocaps;Ilosone;Ilotycin;Ilotycin Gluceptate;IndermRetcin;Kesso-Mycin;Mephamycin;Pantomicina;Pce;Pfizer-e;Propiocine;R-P Mycin;Robimycin;Sansac;Serp-AFD;Stiemycin;Taimoxin-F;Theramycin Z;Torlamicina;Wemid;Wyamycin S;

EM;Erythrocin;Erythrocin Stearate;Erythromycin estolate;Erythromycin ethylsuccinate;Erythromycin glucoheptonate;Erythromycin lactobionate;Erythromycin oxime;Erythromycin Stearate;

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.

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Synthesis Reference

Not Available

General Reference

Kanazawa S, Ohkubo T, Sugawara K: The effects of grapefruit juice on the pharmacokinetics of erythromycin. Eur J Clin Pharmacol. 2001 Jan-Feb;56(11):799-803. Pubmed Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001 Dec;1(2):90-6. Pubmed Okudaira T, Kotegawa T, Imai H, Tsutsumi K, Nakano S, Ohashi K: Effect of the treatment period with erythromycin on cytochrome P450 3A activity in humans. J Clin Pharmacol. 2007 Jul;47(7):871-6. Pubmed

Form	Route	Strength
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

Unit description	Cost	Unit
Benzamycin 5-3% Gel 46.6 gm Jar	236.63 USD	jar
BenzamycinPak 60 5-3% Packets (2 Box Contains 60 Packets)	142.45 USD	packet
Erythromycin 2% Gel 60 gm Tube	46.8 USD	tube
Erycette 60 2% Pad Box	30.99 USD	box
Erythromycin 2% Gel 30 gm Tube	26.2 USD	tube
Erythromycin 2% Solution 60ml Bottle	26.13 USD	bottle
Eryderm 2% Solution 60ml Bottle	25.99 USD	bottle
Erythromycin 5 mg/gm Ointment Limited Supply Available.	13.99 USD	tube
Benzamycin gel	4.95 USD	g
Akne-mycin 2% ointment	3.96 USD	g
PCE 500 mg Enteric Coated Tabs	3.28 USD	tab
Pce 500 mg dispertab	3.03 USD	tablet
PCE 333 mg Enteric Coated Tabs	2.48 USD	tab
Erythromycin e.s. powder	2.39 USD	g
Benzamycinpak gel	2.37 USD	gel
Pce 333 mg dispertab	2.3 USD	tablet
Romycin eye ointment	1.98 USD	g
Erythromycin eye ointment	1.44 USD	g
Pms-Erythromycin 0.5 % Ointment	1.3 USD	g
Emgel 2% topical gel	1.07 USD	g
Ery-Tab 500 mg Enteric Coated Tabs	0.93 USD	tab
Ery-tab 500 mg tablet ec	0.77 USD	tablet
Ery-Tab 333 mg Enteric Coated Tabs	0.72 USD	tab
Erythro-rx powder	0.72 USD	g
Erythromycin ec 500 mg tablet	0.66 USD	tablet
Erythromycin Base 500 mg tablet	0.61 USD	tablet
Eryc 333 mg Capsule (Enteric-Coated Pellet)	0.6 USD	capsule
Apo-Erythro-S 500 mg Tablet	0.57 USD	tablet
E-mycin 333 mg tablet ec	0.54 USD	tablet
Eryc 250 mg Capsule (Enteric-Coated Pellet)	0.54 USD	capsule
Erythromycin powder	0.54 USD	g
Erythromycin 2% gel	0.5 USD	g
Erythromycin Base 250 mg Enteric Coated Capsule	0.5 USD	capsule
Erythromycin Base 250 mg tablet	0.5 USD	tablet
Ery-tab ec 500 mg tablet	0.46 USD	tablet
Apo-Erythro E-C 333 mg Capsule (Enteric-Coated Pellet)	0.45 USD	capsule
Ery-Tab 250 mg Enteric Coated Tabs	0.45 USD	tab
Erythromycin st 500 mg tablet	0.44 USD	tablet
Apo-Erythro E-C 250 mg Capsule (Enteric-Coated Pellet)	0.41 USD	capsule
Ery-tab 333 mg tablet ec	0.4 USD	tablet
Apo-Erythro-Es 600 mg Tablet	0.35 USD	tablet
Erythromycin 500 mg filmtab	0.3 USD	tablet
Erythrocin 500 mg filmtab	0.29 USD	tablet
Ery-tab 250 mg tablet ec	0.27 USD	tablet
E.e.s. 400 filmtab	0.25 USD	tablet
Erythromycin 250 mg filmtab	0.25 USD	tablet
Erythromycin es 400 mg tablet	0.25 USD	tablet
Apo-Erythro-S 250 mg Tablet	0.22 USD	tablet
Apo-Erythro Base 250 mg Tablet	0.19 USD	tablet
Erythrocin 250 mg filmtab	0.16 USD	tablet
Novo-Rythro Ees 80 mg/ml Suspension	0.15 USD	ml
Novo-Rythro Estolate 50 mg/ml Suspension	0.13 USD	ml
Novo-Rythro Ees 40 mg/ml Suspension	0.1 USD	ml

Type	small molecule

Classes

Macrolides

Substructures

Carboxylic Acids and Derivatives Glycerol and Derivatives Hydroxy Compounds Pyrans Acetates Acetals and Derivatives Lactones Ethers Macrolides Aliphatic and Aryl Amines Alcohols and Polyols Heterocyclic compounds Ketones

antibacterials 抗细菌;

Indication	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.
Pharmacodynamics	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.
Mechanism of action	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.
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.
Volume of distribution	Not Available
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. Enzyme Metabolite Reaction Km Vmax Cytochrome P450 3A4 norerythromycin N-demethylation 61 0.88
Route of elimination	Not Available
Half life	0.8 - 3 hours
Clearance	Not Available
Toxicity	Symptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
Affected organisms	Enteric bacteria and other eubacteria
Pathways	Pathway Name SMPDB ID Erythromycin Pathway SMP00250

Properties
State	solid
Melting point	191 oC
Experimental Properties	Property Value Source water solubility Slightly soluble (1.44 mg/L) PhysProp logP 3.06 [MCFARLAND,JW ET AL. (1997)] PhysProp Caco2 permeability -5.43 [ADME Research, USCD] BiGG pKa 8.88 Various sources
Predicted Properties	Property Value Source water solubility 4.59e-01 g/l ALOGPS logP 2.37 ALOGPS logP 2.60 ChemAxon Molconvert logS -3.20 ALOGPS pKa 12.91 ChemAxon Molconvert hydrogen acceptor count 13 ChemAxon Molconvert hydrogen donor count 5 ChemAxon Molconvert polar surface area 193.91 ChemAxon Molconvert rotatable bond count 7 ChemAxon Molconvert refractivity 186.04 ChemAxon Molconvert polarizability 78.21 ChemAxon Molconvert

Drug	Interaction
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.
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.
Dicumarol	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
Dihydroergotoxine	Possible ergotism and severe ischemia with this combination
Disopyramide	Increased risk of cardiotoxicity and arrhythmias
Divalproex sodium	Erythromycin increases the effect of valproic acid
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.
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.
Itraconazole	The macrolide, erythromycin, may increase the effect and toxicity of itraconazole.
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
Methylergonovine	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.
Pimozide	Increased risk of cardiotoxicity and arrhythmias
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.
Rifampin	The rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.
Ritonavir	Increased toxicity of both agents
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.
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.
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.
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).

• Avoid alcohol.
• Take on empty stomach: 1 hour before or 2 hours after meals.
• Take with a full glass of water Avoid taking with grapefruit juice.