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Identification
Name Erythromycin
Accession Number DB00199 (APRD00953)
Type small molecule
Groups approved
Description

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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
EM
Erythrocin Stearate
Erythromycin ethylsuccinate
Erythromycin glucoheptonate
Erythromycin lactobionate
Erythromycin oxime
Erythromycin Stearate
Salts Not Available
Brand names
Name Company
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
Ilocaps
Ilosone
Ilotycin
Ilotycin Gluceptate
IndermRetcin
Kesso-Mycin
Mephamycin
Pantomicina
Pfizer-e
Propiocine
R-P Mycin
Robimycin
Sansac
Stiemycin
Taimoxin-F
Theramycin Z
Torlamicina
Wemid
Wyamycin S
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Brand mixtures
Brand Name Ingredients
Sans-Acne Solution Alcohol Anhydrous + Erythromycin
Staticin Lot Alcohol Anhydrous + Erythromycin + Laureth 4
Stievamycin Forte Gel Erythromycin + Tretinoin
Stievamycin Gel Erythromycin + Tretinoin
T-Stat Lot Alcohol Anhydrous + Erythromycin
T-Stat Pad-Lot Alcohol Anhydrous + Erythromycin
Categories
  • Anti-Bacterial Agents
  • Macrolides
CAS number 114-07-8
Weight Average: 733.9268
Monoisotopic: 733.461241235
Chemical Formula C37H67NO13
InChI Key InChIKey=ULGZDMOVFRHVEP-RWJQBGPGSA-N
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
Plain Text
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
SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
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
Pharmacology
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.
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
Smp00250 Erythromycin Pathway SMP00250
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Parke davis div warner lambert co
  • Warner chilcott inc
  • Abbott laboratories pharmaceutical products div
  • Barr laboratories inc
  • Stiefel laboratories inc
  • Altana inc
  • Merz pharmaceuticals llc
  • Perrigo co
  • Syosset laboratories inc
  • Akorn inc
  • Bausch and lomb pharmaceuticals inc
  • E fougera div altana inc
  • Pharmaderm div altana inc
  • Pharmafair inc
  • Dista products co div eli lilly and co
  • Dow pharmaceutical sciences inc
  • Paddock laboratories inc
  • Taro pharmaceuticals north america inc
  • Bioglan pharma inc
  • Alpharma us pharmaceuticals division
  • Eli lilly and co
  • Perrigo new york inc
  • Wockhardt eu operations (swiss) ag
  • Hi tech pharmacal co inc
  • Westwood squibb pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Orthoneutrogena
  • Versapharm inc
  • Ah robins co
  • Solvay pharmaceuticals
  • Watson laboratories inc
  • Life laboratories inc
  • Lilly research laboratories div eli lilly and co
  • Ross laboratories div abbott laboratories inc
  • Pharmacia and upjohn co
  • Naska pharmacal co inc div rugby darby group cosmetics
  • Wyeth ayerst laboratories
  • Abbott laboratories chemical and agricultural products div
  • Mylan pharmaceuticals inc
  • Elkins sinn div ah robins co inc
  • Abraxis pharmaceutical products
  • Baxter healthcare corp anesthesia and critical care
  • Teva parenteral medicines inc
  • Bristol laboratories inc div bristol myers co
  • Warner chilcott div warner lambert co
  • Lederle laboratories div american cyanamid co
  • Purepac pharmaceutical co
  • Bristol myers squibb co
  • Pfizer laboratories div pfizer inc
Packagers
Dosage forms
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
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Prices
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
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 191 °C PhysProp
water solubility Slightly soluble (1.44 mg/L) Not Available
logP 3.06 MCFARLAND,JW ET AL. (1997)
Caco2 permeability -5.43 ADME Research, USCD
pKa 8.88 (at 25 °C) MCFARLAND,JW ET AL. (1997)
Predicted Properties
Property Value Source
water solubility 4.59e-01 g/l ALOGPS
logP 2.37 ALOGPS
logP 2.6 ChemAxon
logS -3.2 ALOGPS
pKa (strongest acidic) 12.44 ChemAxon
pKa (strongest basic) 8.38 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 13 ChemAxon
hydrogen donor count 5 ChemAxon
polar surface area 193.91 ChemAxon
rotatable bond count 7 ChemAxon
refractivity 186.04 ChemAxon
polarizability 78.21 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. 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
  2. Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001 Dec;1(2):90-6. Pubmed
  3. 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
External Links
Resource Link
KEGG Drug D00140 Link_out
KEGG Compound C01912 Link_out
PubChem Compound 12560 Link_out
PubChem Substance 46508487 Link_out
ChemSpider 12041 Link_out
ChEBI 48923 Link_out
ChEMBL 48923 Link_out
Therapeutic Targets Database DAP000111 Link_out
PharmGKB PA449493 Link_out
HET ERY Link_out
Drug Product Database 2237041 Link_out
RxList http://www.rxlist.com/cgi/generic/erithrom.htm Link_out
Drugs.com http://www.drugs.com/cdi/erythromycin-ointment.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Erythromycin Link_out
ATC Codes
  • D10AF02
  • J01FA01
  • S01AA17
AHFS Codes
  • 34:00.00
  • 08:12.12.04
  • 52:04.04
PDB Entries Not Available
FDA label show (149 KB)
MSDS show (73 KB)
Interactions
Drug Interactions
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.
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.
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
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.
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.
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.
Rifampin The rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.
Ritonavir Increased toxicity of both agents
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.
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).
Food Interactions
  • 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.
Targets

1. 23S rRNA

Pharmacological action: yes
Actions: inhibitor

In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.

Gene Sequence: FASTA

References:
  1. Moazed D, Noller HF: Chloramphenicol, erythromycin, carbomycin and vernamycin B protect overlapping sites in the peptidyl transferase region of 23S ribosomal RNA. Biochimie. 1987 Aug;69(8):879-84. Pubmed
  2. Schlunzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, Franceschi F: Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21. Pubmed
  3. Garza-Ramos G, Xiong L, Zhong P, Mankin A: Binding site of macrolide antibiotics on the ribosome: new resistance mutation identifies a specific interaction of ketolides with rRNA. J Bacteriol. 2001 Dec;183(23):6898-907. Pubmed

2. 50S ribosomal protein L22

Pharmacological action: yes
Actions: inhibitor

The globular domain of the protein is located near the polypeptide exit tunnel on the outside of the subunit, while an extended beta-hairpin is found that lines the wall of the exit tunnel in the center of the 70S ribosome (By similarity)

Organism class: bacterial
UniProt ID: P61177 Link_out
Gene: rplV
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed
  3. Rolain JM, Raoult D: Prediction of resistance to erythromycin in the genus Rickettsia by mutations in L22 ribosomal protein. J Antimicrob Chemother. 2005 Aug;56(2):396-8. Epub 2005 Jul 4. Pubmed
  4. Cagliero C, Mouline C, Cloeckaert A, Payot S: Synergy between efflux pump CmeABC and modifications in ribosomal proteins L4 and L22 in conferring macrolide resistance in Campylobacter jejuni and Campylobacter coli. Antimicrob Agents Chemother. 2006 Nov;50(11):3893-6. Epub 2006 Aug 28. Pubmed
  5. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed
  6. Davydova N, Streltsov V, Wilce M, Liljas A, Garber M: L22 ribosomal protein and effect of its mutation on ribosome resistance to erythromycin. J Mol Biol. 2002 Sep 20;322(3):635-44. Pubmed

3. 50S ribosomal protein L4

Pharmacological action: yes
Actions: inhibitor

Forms part of the polypeptide exit tunnel (By similarity)

Organism class: bacterial
UniProt ID: P60725 Link_out
Gene: rplD
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed
  3. O’Connor M, Gregory ST, Dahlberg AE: Multiple defects in translation associated with altered ribosomal protein L4. Nucleic Acids Res. 2004 Oct 27;32(19):5750-6. Print 2004. Pubmed
  4. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed

2. Cytochrome P450 3A7

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P24462 Link_out
Gene: CYP3A7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 3A5

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20815 Link_out
Gene: CYP3A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 1A2

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Multidrug resistance protein 1

Actions: substrate, inhibitor, inducer

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. Pubmed
  2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed
  3. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. Pubmed
  4. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed
  5. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. Pubmed
  6. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. Pubmed
  7. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. Pubmed
  8. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. Pubmed
  9. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. Epub 2009 Mar 25. Pubmed
  10. Sun H, Huang Y, Frassetto L, Benet LZ: Effects of uremic toxins on hepatic uptake and metabolism of erythromycin. Drug Metab Dispos. 2004 Nov;32(11):1239-46. Epub 2004 Jul 30. Pubmed

2. Multidrug resistance-associated protein 1

Actions: inhibitor

May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics

UniProt ID: P33527 Link_out
Gene: ABCC1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Terashi K, Oka M, Soda H, Fukuda M, Kawabata S, Nakatomi K, Shiozawa K, Nakamura T, Tsukamoto K, Noguchi Y, Suenaga M, Tei C, Kohno S: Interactions of ofloxacin and erythromycin with the multidrug resistance protein (MRP) in MRP-overexpressing human leukemia cells. Antimicrob Agents Chemother. 2000 Jun;44(6):1697-700. Pubmed

3. Solute carrier organic anion transporter family member 1A2

Actions: inhibitor

Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity)

UniProt ID: P46721 Link_out
Gene: SLCO1A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. Pubmed

4. Solute carrier family 22 member 7

Actions: inhibitor

Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate

UniProt ID: Q9Y694 Link_out
Gene: SLC22A7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible involvement of organic anion transporter 2 on the interaction of theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. Pubmed
  2. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19