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114-07-8 molecular structure
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(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 and InChIs

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

Cite this record

CBID:84 http://www.chembase.cn/molecule-84.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
E-Base
Erytromycin A
Aknemycin
Aknin
emgel
Ery-Derm
Erymax
Erythromycin
E-Mycin
Ery-Tab
Erythromid
ERYC
红霉素
CAS Number
114-07-8
EC Number
204-040-1
MDL Number
MFCD00084654
Beilstein Number
75279
PubChem SID
24894374
24894626
24894612
160963547
46508487
PubChem CID
12560

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.438841  H Acceptors 13 
H Donor LogD (pH = 5.5) -0.1920999 
LogD (pH = 7.4) 1.5732646  Log P 2.5963888 
Molar Refractivity 186.0371 cm3 Polarizability 75.76136 Å3
Polar Surface Area 193.91 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 2.37  LOG S -3.2 
Solubility (Water) 4.59e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
2 M HCl: soluble50 mg/mL (Stock solutions should be stored at 2-8 °C. Stable at 37 °C for 3 days.) expand Show data source
Acetone expand Show data source
Acetonitrile expand Show data source
Chloroform expand Show data source
Ethanol expand Show data source
ethanol: soluble (Stock solutions should be stored at 2-8 °C. Stable at 37 °C for 3 days.) expand Show data source
Ethyl Acetate expand Show data source
Slightly soluble (1.44 mg/L) expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
193-195°C expand Show data source
Hydrophobicity(logP)
3.06 [MCFARLAND,JW ET AL. (1997)] expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
KF437500 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Gene Information
human ... ABCB1(5243), CYP3A4(1576), MLNR(2862)mouse ... Abcb1a(18671), Abcb1b(18669) expand Show data source
Purity
~98% expand Show data source
Potency
≥850 μg per mg expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
Impurities
≤0.1 EU/mg endotoxin expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00199 external link
Item Information
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 external link
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 - E0774 external link
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.
Sigma Aldrich - E6376 external link
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 - E4514 external link
Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

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