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MedKoo Cat#: 463287 | Name: Erythromycin ethylsuccinate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Erythromycin ethylsuccinate is a potent prokinetic agent that stimulates gastric emptying. It is also used as an antibiotic to treat infection.

Chemical Structure

Erythromycin ethylsuccinate
Erythromycin ethylsuccinate
CAS#1264-62-6 (ethylsuccinate)

Theoretical Analysis

MedKoo Cat#: 463287

Name: Erythromycin ethylsuccinate

CAS#: 1264-62-6 (ethylsuccinate)

Chemical Formula: C43H75NO16

Exact Mass: 861.5086

Molecular Weight: 862.06

Elemental Analysis: C, 59.91; H, 8.77; N, 1.62; O, 29.69

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
7704-67-8 (thiocyanate) 114-07-8 (free base) 30010-41-4 (aspartate) 14271-02-4 (HCl) 16667-03-1 (glutamate) 3521-62-8 (estolate) 914076-30-5 (ethyl carbonate) 134-36-1 (propionate) 1264-62-6 (ethylsuccinate) 23067-13-2 (Gluceptate)
Synonym
erythromycin ethylsuccinate; Erythromycin ethyl succinate; Pediamycin; Erythroped
IUPAC/Chemical Name
(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
InChi Key
NSYZCCDSJNWWJL-YXOIYICCSA-N
InChi Code
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
SMILES Code
CCOC(CCC(O[C@H]1[C@@H](O[C@@H](C[C@@H]1N(C)C)C)O[C@@H]2[C@H]([C@@H]([C@H](C(O[C@@H]([C@@](O)([C@@H]([C@H](C([C@@H](C[C@]2(O)C)C)=O)C)O)C)CC)=O)C)O[C@H]3C[C@@](OC)([C@H]([C@@H](O3)C)O)C)C)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 862.06 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Stan CD, Stefanache A, Tântaru G, Poiată A, Dumitrache M, Diaconu DE, Profire L. Posibilităţi de obtinere a etil-succinatului de eritromicină [Erythromycin ethylsuccinate obtaining possibilities]. Rev Med Chir Soc Med Nat Iasi. 2008 Oct-Dec;112(4):1104-9. Romanian. PMID: 20209795. 2: Viteri AL, Greene JF Jr, Dyck WP. Erythromycin ethylsuccinate-induced cholestasis. Gastroenterology. 1979 May;76(5 Pt 1):1007-8. PMID: 437404. 3: Moshiree B, McDonald R, Hou W, Toskes PP. Comparison of the effect of azithromycin versus erythromycin on antroduodenal pressure profiles of patients with chronic functional gastrointestinal pain and gastroparesis. Dig Dis Sci. 2010 Mar;55(3):675-83. doi: 10.1007/s10620-009-1038-3. PMID: 19924535. 4: Lakritz J, Wilson WD, Marsh AE, Mihalyi JE. Pharmacokinetics of erythromycin ethylsuccinate after intragastric administration to healthy foals. Vet Ther. 2002 Summer;3(2):189-95. PMID: 19750750. 5: Choo JM, Abell GCJ, Thomson R, Morgan L, Waterer G, Gordon DL, Taylor SL, Leong LEX, Wesselingh SL, Burr LD, Rogers GB. Impact of Long-Term Erythromycin Therapy on the Oropharyngeal Microbiome and Resistance Gene Reservoir in Non- Cystic Fibrosis Bronchiectasis. mSphere. 2018 Apr 18;3(2):e00103-18. doi: 10.1128/mSphere.00103-18. PMID: 29669883; PMCID: PMC5907653. 6: Gu Y, Wang G, Sun J. Simultaneous determination of erythromycin ethylsuccinate and its metabolite erythromycin in human plasma using liquid chromatography-electrospray ionization mass spectrometry for clinical study. J Pharm Biomed Anal. 2006 Feb 24;40(3):737-43. doi: 10.1016/j.jpba.2005.11.005. Epub 2006 Jan 10. PMID: 16376051. 7: Yakatan GJ, Rasmussen CE, Feis PJ, Wallen S. Bioinequivalence of erythromycin ethylsuccinate and enteric-coated erythromycin pellets following multiple oral doses. J Clin Pharmacol. 1985 Jan-Feb;25(1):36-42. doi: 10.1002/j.1552-4604.1985.tb02798.x. PMID: 3871797. 8: Croteau D, Bergeron MG, LeBel M. Pharmacokinetic advantages of erythromycin estolate over ethylsuccinate as determined by high-pressure liquid chromatography. Antimicrob Agents Chemother. 1988 Apr;32(4):561-5. doi: 10.1128/aac.32.4.561. PMID: 3259856; PMCID: PMC172220. 9: Sullivan D, Csuka ME, Blanchard B. Erythromycin ethylsuccinate hepatotoxicity. JAMA. 1980 Mar 14;243(10):1074. PMID: 6965509. 10: Shanson DC, Tidbury P, McNabb WR, Tadayon M. The pharmacokinetics and tolerance of oral erythromycin stearate compared with erythromycin ethylsuccinate: implications for preventing endocarditis. J Antimicrob Chemother. 1984 Aug;14(2):157-63. doi: 10.1093/jac/14.2.157. PMID: 6334070. 11: Bérubé D, Kirouac D, Croteau D, Bergeron MG, Lebel M. Plasma bactericidal activity after administration of erythromycin estolate and erythromycin ethylsuccinate to healthy volunteers. Antimicrob Agents Chemother. 1988 Aug;32(8):1227-30. doi: 10.1128/aac.32.8.1227. PMID: 3142349; PMCID: PMC172382. 12: Hoppe JE. Comparison of erythromycin estolate and erythromycin ethylsuccinate for treatment of pertussis. The Erythromycin Study Group. Pediatr Infect Dis J. 1992 Mar;11(3):189-93. doi: 10.1097/00006454-199203000-00003. PMID: 1565532. 13: Potthast H, Schug B, Elze M, Schwerdtle R, Blume H. Vergleich der Bioverfügbarkeiten von Erythromycinestolat bzw. Erythromycinethylsuccinat enthaltenden Trockensaft-Zubereitungen im steady state [Comparison of the bioavailabilities of erythromycin estolate and erythromycin ethylsuccinate dry suspension preparations in steady state]. Pharmazie. 1995 Jan;50(1):56-60. German. PMID: 7886126. 14: Ginsburg CM, McCracken GH Jr, Crow SD, Dildy BR, Morchower G, Steinberg JB, Lancaster K. Erythromycin therapy for group A streptococcal pharyngitis. Results of a comparative study of the estolate and ethylsuccinate formulations. Am J Dis Child. 1984 Jun;138(6):536-9. doi: 10.1001/archpedi.1984.02140440020004. PMID: 6372437. 15: Patamasucon P, Kaojarern S, Kusmiesz H, Nelson JD. Pharmacokinetics of erythromycin ethylsuccinate and estolate in infants under 4 months of age. Antimicrob Agents Chemother. 1981 May;19(5):736-9. doi: 10.1128/aac.19.5.736. PMID: 6975059; PMCID: PMC181514. 16: Cachet T, Lannoo P, Paesen J, Janssen G, Hoogmartens J. Determination of erythromycin ethylsuccinate by liquid chromatography. J Chromatogr. 1992 May 27;600(1):99-108. doi: 10.1016/0021-9673(92)85443-w. PMID: 1400845. 17: Delatour F, Le Guludec D, Caron F, Faurisson F, Torlotin JC, Rouveix B. Effect of a single oral dose of two erythromycin ethylsuccinate formulations on gastric emptying in healthy volunteers: a scintigraphic study. Fundam Clin Pharmacol. 1998;12(3):292-7. doi: 10.1111/j.1472-8206.1998.tb00957.x. PMID: 9646062. 18: Keeffe EB, Reis TC, Berland JE. Hepatotoxicity to both erythromycin estolate and erythromycin ethylsuccinate. Dig Dis Sci. 1982 Aug;27(8):701-4. doi: 10.1007/BF01393764. PMID: 6980110. 19: Liu YM, Shi YM, Liu ZL, Peng LF. Sensitive determination of tilmicosin, erythromycin ethylsuccinate and clindamycin by CE with electrochemiluminescence detection using azithromycin as internal standard and its applications. J Sep Sci. 2010 May;33(9):1305-11. doi: 10.1002/jssc.200900843. PMID: 20235137. 20: Gustafsson A, Båverud V, Gunnarsson A, Rantzien MH, Lindholm A, Franklin A. The association of erythromycin ethylsuccinate with acute colitis in horses in Sweden. Equine Vet J. 1997 Jul;29(4):314-8. doi: 10.1111/j.2042-3306.1997.tb03129.x. PMID: 15338913.