ERY

ERYTHROMYCIN A

Created:	2001-09-18
Last modified:	2011-06-04

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40 entries where ERY is found as a standalone ligand1 entries where ERY is covalently linked to polymer or other heterogen groups

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Chemical Details
Formal Charge	0
Atom Count	118
Chiral Atom Count	18
Bond Count	120
Aromatic Bond Count	0

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Chemical Component Summary
Name	ERYTHROMYCIN A
Systematic Name (OpenEye OEToolkits)	(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
Formula	C₃₇ H₆₇ N O₁₃
Molecular Weight	733.927
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C3OC(CC)C(O)(C)C(O)C(C(=O)C(C)CC(O)(C)C(OC1OC(C)CC(N(C)C)C1O)C(C(OC2OC(C(O)C(OC)(C2)C)C)C3C)C)C
SMILES	CACTVS	3.341	CC[CH]1OC(=O)[CH](C)[CH](O[CH]2C[C](C)(OC)[CH](O)[CH](C)O2)[CH](C)[CH](O[CH]3O[CH](C)C[CH]([CH]3O)N(C)C)[C](C)(O)C[CH](C)C(=O)[CH](C)[CH](O)[C]1(C)O
SMILES	OpenEye OEToolkits	1.5.0	CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
Canonical SMILES	CACTVS	3.341	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]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
InChI	InChI	1.03	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
InChIKey	InChI	1.03	ULGZDMOVFRHVEP-RWJQBGPGSA-N

Drug Info: DrugBank

DrugBank ID	DB00199
Name	Erythromycin
Groups	approved vet_approved investigational
Description	Erythromycin is a bacteriostatic antibiotic drug produced by a strain of Saccharopolyspora erythraea (formerly Streptomyces erythraeus) and belongs to the macrolide group of antibiotics which consists of [Azithromycin], [Clarithromycin], [Spiramycin] and others. It was originally discovered in 1952.[L5245] Erythromycin is widely used for treating a variety of infections, including those caused by gram-positive and gram-negative bacteria.[L5245,L7261] It is available for administration in various forms, including intravenous, topical, and eye drop preparations.[L5245]
Synonyms	Erythromycinum Erythromycin Erythromycin sulfate 3''-O-demethylerythromycin Erythromycin ethylsuccinate Erythromycin phosphate Erythromycin gluceptate Erythromycin estolate Abomacetin Erythromycin stearate Erythromycin thiocyanate Eritromicina Erythromycin A Erythromycin C Erythromycin lactobionate érythromycine
Brand Names	T-stat Pad-lot Ilosone 250mg Pulvule 375 Erythro-ES Stievamycin Mild Pediazole Alti-erythromycin Tab 250mg USP Benzamycin Pak Ees-200 Chewable Tbs (eryped) Erythromycin Stearate Tablets USP 250mg Pdp-erythromycin Novo-rythro Stearate Tab 250mg Erymycin Ophthalmic Ointment 5mg/g Ees-400 Erythromycin Capsules USP 250mg Erythrocin Filmtab 250mg Euro-erythromycin Ophthalmic Ointment USP Erythra-Derm Erythromycin Ophthalmic Ointment U.S.P. Eryc Delayed-release Capsules Erythro-S Erythromycin Maxitril Pce Erythromycin and Benzoyl Peroxide Erythromycin Gel Ery-Tab Erythrocin I.V. E.E.s 400 Erythro-base Erythro-ES Tab 600mg USP Ilosone Liquid 250mg/5ml Erythromycin Base Stievamycin Regular Erythromycin Base Filmtab Erythro-EC EryPed 200 Novo-rythro Estolate Suspension Ilosone Liquid 125mg/5ml Erythromycin Ethylsuccinate and Sulfisoxazole Acetyl Novo-rythro Ethylsuccinate Pwr 400mg/5ml Erythrocin Liq 250 Eryc Erybid Novo-rythro Estolate Cap 250mg Erythromycin-Benzoyl Peroxide EryPed Erythromycin Base Base Ees-200 E.E.S. EryPed Drops ERYTHROMYCIN Base Filmtab Erythromycin Ethylsuccinate Mytrophene Akne-mycin Ery-Ped Erythrocin Liquid 125 Spotex PMS-erythromycin E.E.s Erythrocin Filmtab 500mg T-Stat Erythromycin Lactobionate Erythrocin Stearate Nu-erythromycin-S 250mg Tablets Erythrocin IV Benzamycin Ilotycin Cryst Op Ont 0.5% 52 Sterile Erythromycin Lactobionate Pws 1000mg Erythrocin Lactobionate Erythro-base Tab 250mg USP Odan-erythromycin Novo-rythro Encap 250mg Erygel Erysol Erythromycin ethylsuccinate Erythromycine 250 Tab Aktipak Ery-tab Stievamycin Forte EryPed 400 Erythromycin Ophthalmic Ointment USP Ilotycin Erythro-500 Tab 500mg USP Sans-acne Solution Erythromid Tab 250mg Ery Ilotycin Gluceptate IV Ampoule 646 1gm Sterile Erythromycin Lactobionate Pws 500mg Ees 600 Tablets 600mg Emycin Ect 250mg Novo-rythro Ethylsuccinate Pws Staticin T-stat Lot
Indication	Erythromycin is indicated in the treatment of infections caused by susceptible strains of various bacteria.[L7261] The indications for erythromycin have been summarized by body system below: Respiratory infections Mild to moderate upper respiratory tract infections caused by Streptococcus pyogenes, Streptococcus pneumoniae, or Haemophilus influenzae (when used concomitantly with appropriate doses of sulfonamides) can be treated with erythromycin.[L7261] Mild to moderate lower-respiratory tract infections due to susceptible strains of Streptococcus pneumoniae or Streptococcus pyogenes may also be treated. Erythromycin treats listeriosis caused by Listeria monocytogenes may also be treated with erythromycin.[L7261] Erythromycin is indicated to treat pertussis (whooping cough) caused by Bordetella pertussis. It is effective in eliminating the causative organism from the nasopharynx of infected individuals, rendering them noninfectious. Clinical studies suggest that erythromycin may aid in the prevention of pertussis infection for individuals who have been exposed to the bacteria.[L7261] Respiratory tract infections due to Mycoplasma pneumoniae may also be treated with erythromycin.[L7261] Despite the fact that no controlled clinical efficacy studies have been conducted to this date, in vitro and certain preliminary clinical study results indicate that erythromycin may be an effective treatment in Legionnaires’ Disease.[L7261] Finally, erythromycin is indicated to treat diphtheria and other infections due to Corynebacterium diphtheriae, as an adjunct to antitoxin, to prevent carrier status and to eradicate the organism in existing carriers.[L7261] In addition to the prevention of diphtheria, erythromycin can be used to prevent rheumatic fever in penicillin intolerant patients.[L7261] Skin infections Mild to moderate skin or skin structure infections caused by Streptococcus pyogenes or Staphylococcus aureus may be treated with erythromycin, however, resistant staphylococcal organisms may emerge.[L7261] Erythromycin can also be used to treat erythrasma, an infectious condition caused by Corynebacterium minutissimum.[L7261] Gastrointestinal infections Intestinal amebiasis caused by Entamoeba histolytica can be treated with oral erythromycin. Extraenteric amebiasis warrants treatment with other antimicrobial drugs.[L7261] Genital infections/STIs Erythromycin can be used as an alternative drug in treating acute pelvic inflammatory disease caused by N. gonorrheae in female patients who have demonstrated hypersensitivity or intolerance to penicillin.[L7261] Syphilis, caused by Treponema pallidum, can be treated with erythromycin. It serves as an alternative treatment for primary syphilis in patients who have demonstrated penicillin hypersensitivity. Erythromycin can also be used in the primary stage of primary syphilis.[L7261] Another approved indication of erythromycin is to treat chlamydial infections that cause conjunctivitis of the newborn, pneumonia of infancy, and urogenital infections occurring in pregnancy. It is indicated as an alternative option to tetracyclines for the treatment of uncomplicated rectal, urethral and endocervical infections in adults caused by Chlamydia trachomatis.[L7261] Erythromycin can be used in nongonococcal urethritis can be used when tetracyclines cannot be administered. Finally, erythromycin is indicated to treat nongonococcal urethritis due to Ureaplasma urealyticum.[L7261]
Categories	Anti-Acne Preparations Anti-Acne Preparations for Topical Use Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antiinfectives for Systemic Use Antiinfectives for Treatment of Acne BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (moderate) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (moderate) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (moderate) Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dermatologicals Enzyme Inhibitors Erythromycin and similars Erythromycins Gastrointestinal Agents Lactones Macrolide Antimicrobial Macrolides Macrolides, Lincosamides and Streptogramins Moderate Risk QTc-Prolonging Agents OATP1B1/SLCO1B1 Inhibitors OATP1B1/SLCO1B1 Substrates OATP1B3 inhibitors OATP1B3 substrates Ophthalmologicals P-glycoprotein inhibitors P-glycoprotein substrates Protein Synthesis Inhibitors QTc Prolonging Agents
ATC-Code	J01FA01 D10AF02 S01AA17 D10AF52
CAS number	114-07-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
23S ribosomal RNA	-	unknown	inhibitor
Motilin receptor	MGSPWNGSDGPEGAREPPWPALPPCDERRCSPFPLGALVPVTAVCLCLFV...	unknown	agonist
Potassium voltage-gated channel subfamily H member 2	MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...	unknown	inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate,inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	substrate,inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	substrate,inhibitor
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	substrate
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	substrate,inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682