ERYTHROMYCIN ETHYLSUCCINATE
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| Category | Antibiotics |
| Catalog number | BBF-03813 |
| CAS | 1264-62-6 |
| Molecular Weight | 862.05 |
| Molecular Formula | C43H75NO16 |
| Purity | ≥98% |
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Description
Erythromycin Ethylsuccinate, an oral macrolide antibiotic produced by Streptomyces erythreus, reversibly binds to the 50S ribosome of bacteria, and inhibits protein synthesis.
Specification
| Related CAS | 1334-36-7 (Deleted CAS) 1386-36-3 (Deleted CAS) 7121-45-1 (Deleted CAS) 12125-46-1 (Deleted CAS) 22372-15-2 (Deleted CAS) 41342-53-4 (Deleted CAS) 68206-56-4 (Deleted CAS) 314725-13-8 (Deleted CAS) |
| Synonyms | Pediamycin; EryPed; Wyamycin E; Erythromycin ethyl succinate; Erythromycin, 2'-(ethyl butanedioate); Erythroped; Erythromycin A Ethylsuccinate; (2S,3R,4S,6R)-4-(Dimethylamino)-2-{[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl]oxy}-6-methyltetrahydro-2H-pyran-3-yl ethyl succinate; Erythromycin, mono(ethyl succinate) (ester); Succinic acid, ethyl ester, monoester with erythromycin; Anamycin; Arpimycin; Durapaediat; Monomycin; Paediathrocin; Refkas; Sigapedil |
| Storage | Store at -20°C |
| IUPAC Name | 4-O-[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] 1-O-ethyl butanedioate |
| Canonical SMILES | 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)OC(=O)CCC(=O)OCC)(C)O)C)C)O)(C)O |
| InChI | InChI=1S/C43H75NO16/c1-15-29-43(11,52)36(48)24(5)33(47)22(3)20-41(9,51)38(25(6)34(26(7)39(50)57-29)59-32-21-42(10,53-14)37(49)27(8)56-32)60-40-35(28(44(12)13)19-23(4)55-40)58-31(46)18-17-30(45)54-16-2/h22-29,32,34-38,40,48-49,51-52H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,32+,34+,35-,36-,37+,38-,40+,41-,42-,43-/m1/s1 |
| InChI Key | NSYZCCDSJNWWJL-YXOIYICCSA-N |
| Source | Saccharopolyspora Erythraea |
Properties
| Appearance | White Crystalline Powder |
| Boiling Point | 874.1±65.0°C at 760 mmHg |
| Melting Point | 109-110°C |
| Flash Point | 482.4±34.3 °C |
| Density | 1.21±0.1 g/cm3 |
| Solubility | Soluble in Acetone (Freely), Anhydrous Ethanol, Methanol, Water (Practically) |
Reference Reading
1.Sensitive determination of tilmicosin, erythromycin ethylsuccinate and clindamycin by CE with electrochemiluminescence detection using azithromycin as internal standard and its applications.
Liu YM1, Shi YM, Liu ZL, Peng LF. J Sep Sci. 2010 May;33(9):1305-11. doi: 10.1002/jssc.200900843.
A sensitive approach for the simultaneous determination of tilmicosin, erythromycin ethylsuccinate and clindamycin was developed by CE coupled with electrochemiluminescence detection with ionic liquid. The parameters for CE, electrochemiluminescence detection and the effect of ionic liquid were investigated systematically. The three analytes were well separated and detected within 8 min. The limits of detection (S/N=3) of tilmicosin, erythromycin ethylsuccinate and clindamycin are 3.4x10(-9), 2.3x10(-8) and 1.3x10(-8) mol/L, respectively. The precisions (RSD%) of the peak area and the migration time are from 0.8 to 1.5% and from 0.2 to 0.5% within a day and from 1.8 to 2.7% and from 0.6 to 0.8% in 3 days, respectively. The limits of quantitation (S/N=10) of tilmicosin, erythromycin ethylsuccinate and clindamycin are 3.2x10(-8), 2.9x10(-7) and 9.1x10(-8) mol/L in human urines and 5.5x10(-8), 3.2x10(-7) and 2.1x10(-7) mol/L in milk samples, respectively.
2.Effects of curcumin on the pharmacokinetics of tamoxifen and its active metabolite, 4-hydroxytamoxifen, in rats: possible role of CYP3A4 and P-glycoprotein inhibition by curcumin.
Cho YA1, Lee W, Choi JS. Pharmazie. 2012 Feb;67(2):124-30.
The effects of curcumin, a natural anti-cancer compound, on the bioavailability and pharmacokinetics of tamoxifen and its metabolite, 4-hydroxytamoxifen, were investigated in rats. Tamoxifen and curcumin interact with cytochrom P450 (CYP) enzymes and P-glycoprotein, and the increase in the use of health supplements may result in curcumin being taken concomitantly with tamoxifen as a combination therapy to treat or prevent cancer. A single dose of tamoxifen was administered orally (9 mg x kg(-1)) with or without curcumin (0.5, 2.5 and 10 mg x kg(-1)) and intravenously (2mg x kg(-1)) with or without curcumin (2.5 and 10 mg x kg(-1)) to rats. The effects of curcumin on P-glycoprotein (P-gp) and CYP3A4 activity were also evaluated. Curcumin inhibited CYP3A4 activity with 50% inhibition concentration (IC50) values of 2.7 microM. In addition, curcumin significantly (P < 0.01 at 10 microM) enhanced the cellular accumulation of rhodamine-123 in MCF-7/ADR cells overexpressing P-gp in a concentration-dependent manner.
3.The effect of long-term macrolide treatment on respiratory microbiota composition in non-cystic fibrosis bronchiectasis: an analysis from the randomised, double-blind, placebo-controlled BLESS trial.
Rogers GB1, Bruce KD2, Martin ML3, Burr LD4, Serisier DJ5. Lancet Respir Med. 2014 Dec;2(12):988-96. doi: 10.1016/S2213-2600(14)70213-9. Epub 2014 Oct 14.
BACKGROUND: Long-term macrolide treatment has proven benefit in inflammatory airways diseases, but whether it leads to changes in the composition of respiratory microbiota is unknown. We aimed to assess whether long-term, low-dose erythromycin treatment changes the composition of respiratory microbiota in people with non-cystic fibrosis bronchiectasis.
4.Randomized controlled trial of a high dose of oral erythromycin for the treatment of feeding intolerance in preterm infants.
Mansi Y1, Abdelaziz N, Ezzeldin Z, Ibrahim R. Neonatology. 2011;100(3):290-4. doi: 10.1159/000327536. Epub 2011 Jun 23.
OBJECTIVES: To evaluate the effectiveness of high-dose erythromycin to treat feeding intolerance in preterm infants predominantly fed milk formula.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
