(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

• ChemBase ID: 84
• Molecular Formular: C37H67NO13
• Molecular Mass: 733.92678
• Monoisotopic Mass: 733.46124121
• SMILES: O([C@@H]1[C@H]([C@H](O[C@@H]2O[C@H]([C@H](O)[C@](OC)(C2)C)C)[C@H](C(=O)O[C@@H]([C@@](O)([C@H](O)[C@H](C(=O)[C@@H](C[C@]1(O)C)C)C)C)CC)C)C)[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C
• Canonical SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)O
• 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
• InChIKey: ULGZDMOVFRHVEP-RWJQBGPGSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: erythromycin
• Brand Name: Abboticin; Abomacetin; Ak-mycin; Akne-Mycin; Aknin; Benzamycin; Benzamycin Pak; Bristamycin; Dotycin; Dumotrycin; E-Base; E-Glades; E-Mycin; E-Solve 2; EMU; ETS; Emgel; 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; Pce; Pfizer-e; Propiocine; R-P Mycin; Robimycin; Sansac; Serp-AFD; Stiemycin; Taimoxin-F; Theramycin Z; Torlamicina; Wemid; Wyamycin S
• Synonyms: E-Base; Erytromycin A; Aknemycin; Aknin; emgel; Ery-Derm; Erymax; Ery-Tab; Erythromid; ERYC; E-Mycin; Erythromycin estolate; Erythromycin ethylsuccinate; Erythromycin glucoheptonate; Erythromycin lactobionate; Erythromycin oxime; Erythromycin Stearate; Erythrocin Stearate; Erythrocin; EM; Erythromycin; (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-dimethylte trahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyloxa cyclotetradecane-2,10-dione; Erythromycin; 红霉素

Database IDs

• CAS Number: 114-07-8
• EC Number: 204-040-1
• MDL Number: MFCD00084654
• Beilstein Number: 75279
• PubChem SID: 24894374; 46508487; 160963547; 24894612; 24894626
• PubChem CID: 12560

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.438841
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -0.1920999
• LogD (pH = 7.4): 1.5732646
• Log P: 2.5963888
• Molar Refractivity: 186.0371 cm^3
• Polarizability: 75.76136 Å^3
• Polar Surface Area: 193.91 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.37
• LOG S: -3.2
• Solubility (Water): 4.59e-01 g/l

PROPERTIES

Physical Property

• Solubility: 2 M HCl: soluble50 mg/mL (Stock solutions should be stored at 2-8 °C. Stable at 37 °C for 3 days.); Acetone; Acetonitrile; Chloroform; Ethanol; ethanol: soluble (Stock solutions should be stored at 2-8 °C. Stable at 37 °C for 3 days.); Ethyl Acetate; Slightly soluble (1.44 mg/L)
• Apperance: powder; White Solid
• Melting Point: 193-195°C
• Hydrophobicity(logP): 3.06 [MCFARLAND,JW ET AL. (1997)]

Safety Information

• Storage Condition: Refrigerator
• RTECS: KF437500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ABCB1(5243), CYP3A4(1576), MLNR(2862)mouse ... Abcb1a(18671), Abcb1b(18669)

Product Information

• Purity: ~98%
• Potency: ≥850 μg per mg
• Suitability: meets USP testing specifications; plant cell culture tested; suitable for cell culture
• Impurities: ≤0.1 EU/mg endotoxin

DETAILS

DrugBank - DB00199

• Drug 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.
• 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.
• Pharmacology: 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.
• Toxicity: Symptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: 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.
• 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.
• Half Life: 0.8 - 3 hours
• Protein Binding: Erythromycin is largely bound to plasma proteins, ranging from 75 - 95% binding depending on the form.
• References: 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]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - E5389

Application
Recommended for use in cell culture applications at 100 mg/L
Biochem/physiol Actions
Inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site).
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - E4514

Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.

Sigma Aldrich - E6376

Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Mode of Action: Inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site).Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.

Sigma Aldrich - E0774

Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step (aminoacyl translocation A-site to P-site).Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.

Toronto Research Chemicals - E649950

Antibiotic.

REFERENCES

• 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
• Koch, W.L., et al.: Anal. Profiles Drug Subs., 8, 157 (1979)