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MedKoo Cat#: 598459 | Name: Erythromycin estolate
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Description:

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

Erythromycin estolate is a macrolide antibiotic, produced by Streptomyces erythreus. It is the lauryl sulfate salt of the propionic ester of erythromycin. This erythromycin salt acts primarily as a bacteriostatic agent. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.

Chemical Structure

Erythromycin estolate
Erythromycin estolate
CAS#3521-62-8 (estolate)

Theoretical Analysis

MedKoo Cat#: 598459

Name: Erythromycin estolate

CAS#: 3521-62-8 (estolate)

Chemical Formula: C52H97NO18S

Exact Mass: 0.0000

Molecular Weight: 1056.39

Elemental Analysis: C, 59.12; H, 9.26; N, 1.33; O, 27.26; S, 3.03

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 weeks
10g USD 450.00 2 weeks
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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 estolate; Ilosone; Lauromicina; Erythromycinestolate; Marcoeritrex; NSC 263364; NSC-263364; NSC263364;
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 propionate dodecyl sulfate
InChi Key
AWMFUEJKWXESNL-JZBHMOKNSA-N
InChi Code
InChI=1S/C40H71NO14.C12H26O4S/c1-15-27-40(11,48)33(44)22(5)30(43)20(3)18-38(9,47)35(55-37-32(53-28(42)16-2)26(41(12)13)17-21(4)50-37)23(6)31(24(7)36(46)52-27)54-29-19-39(10,49-14)34(45)25(8)51-29;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h20-27,29,31-35,37,44-45,47-48H,15-19H2,1-14H3;2-12H2,1H3,(H,13,14,15)/t20-,21-,22+,23+,24-,25+,26+,27-,29+,31+,32-,33-,34+,35-,37+,38-,39-,40-;/m1./s1
SMILES Code
CCCCCCCCCCCCOS(=O)(O)=O.CC[C@H]1OC([C@@H]([C@H]([C@@H]([C@H]([C@](O)(C[C@H](C([C@@H]([C@H]([C@@]1(O)C)O)C)=O)C)C)O[C@@H]2O[C@@H](C[C@H](N(C)C)[C@H]2OC(CC)=O)C)C)O[C@H]3C[C@@](OC)([C@H]([C@@H](O3)C)O)C)C)=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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Erythromycin estolate, erythromycin derivative, is a macrolide antibiotic used in the treatment of a wide variety of bacterial infections.
In vitro activity:
As shown in Figure 1B, numbers of ZIKV plaques were reduced more as the concentration of Ery-Est (erythromycin estolate) increased. There were scarcely any plaques formed with the Ery-Est treatment of 10 µM or more, while plaques treated by Ery of any concentrations used in the assay were generally unchanged. This suggests that Ery-Est inhibits ZIKV infection in a dose-dependent manner. Reference: Viruses. 2019 Nov; 11(11): 1064. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6893414/
In vivo activity:
Additionally, the ERM (erythromycin) treatment significantly reduced bone loss compared to the PC and JSM treatment groups (Figure 1b,c). Compared to the EtOH group, ERM, JSM, and PC treatment significantly decreased the gene expression of Nfatc1 and RANK, which are osteoclast differentiation-related factors in the gingiva (Figure 2a,b). Furthermore, ERM and JSM treatment significantly downregulated the expression of bone resorption activity-related factors (Acp5, Ctsk) (Figure 2c,d). Interestingly, ERM treatment significantly upregulated Del1 expression, compared to the EtOH group (Figure 2e). Reference: Antibiotics (Basel). 2021 Mar; 10(3): 312. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8002756/
Solvent mg/mL mM
Solubility
DMSO 100.0 94.66
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,056.39 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
Formulation protocol:
1. Wang X, Xia S, Zou P, Lu L. Erythromycin Estolate Inhibits Zika Virus Infection by Blocking Viral Entry as a Viral Inactivator. Viruses. 2019 Nov 15;11(11):1064. doi: 10.3390/v11111064. PMID: 31731598; PMCID: PMC6893414. 2. Liu J, Zhong X, He Z, Zhang J, Bai J, Liu G, Liang Y, Ya L, Qin X. Erythromycin Suppresses the Cigarette Smoke Extract-Exposed Dendritic Cell-Mediated Polarization of CD4+ T Cells into Th17 Cells. J Immunol Res. 2020 Jan 21;2020:1387952. doi: 10.1155/2020/1387952. PMID: 32411785; PMCID: PMC7201779. 3. Tamura H, Maekawa T, Domon H, Hiyoshi T, Hirayama S, Isono T, Sasagawa K, Yonezawa D, Takahashi N, Oda M, Maeda T, Tabeta K, Terao Y. Effects of Erythromycin on Osteoclasts and Bone Resorption via DEL-1 Induction in Mice. Antibiotics (Basel). 2021 Mar 17;10(3):312. doi: 10.3390/antibiotics10030312. PMID: 33803007; PMCID: PMC8002756. 4. Maekawa T, Tamura H, Domon H, Hiyoshi T, Isono T, Yonezawa D, Hayashi N, Takahashi N, Tabeta K, Maeda T, Oda M, Ziogas A, Alexaki VI, Chavakis T, Terao Y, Hajishengallis G. Erythromycin inhibits neutrophilic inflammation and mucosal disease by upregulating DEL-1. JCI Insight. 2020 Aug 6;5(15):e136706. doi: 10.1172/jci.insight.136706. PMID: 32603314; PMCID: PMC7455085.
In vitro protocol:
1. Wang X, Xia S, Zou P, Lu L. Erythromycin Estolate Inhibits Zika Virus Infection by Blocking Viral Entry as a Viral Inactivator. Viruses. 2019 Nov 15;11(11):1064. doi: 10.3390/v11111064. PMID: 31731598; PMCID: PMC6893414. 2. Liu J, Zhong X, He Z, Zhang J, Bai J, Liu G, Liang Y, Ya L, Qin X. Erythromycin Suppresses the Cigarette Smoke Extract-Exposed Dendritic Cell-Mediated Polarization of CD4+ T Cells into Th17 Cells. J Immunol Res. 2020 Jan 21;2020:1387952. doi: 10.1155/2020/1387952. PMID: 32411785; PMCID: PMC7201779.
In vivo protocol:
1. Tamura H, Maekawa T, Domon H, Hiyoshi T, Hirayama S, Isono T, Sasagawa K, Yonezawa D, Takahashi N, Oda M, Maeda T, Tabeta K, Terao Y. Effects of Erythromycin on Osteoclasts and Bone Resorption via DEL-1 Induction in Mice. Antibiotics (Basel). 2021 Mar 17;10(3):312. doi: 10.3390/antibiotics10030312. PMID: 33803007; PMCID: PMC8002756. 2. Maekawa T, Tamura H, Domon H, Hiyoshi T, Isono T, Yonezawa D, Hayashi N, Takahashi N, Tabeta K, Maeda T, Oda M, Ziogas A, Alexaki VI, Chavakis T, Terao Y, Hajishengallis G. Erythromycin inhibits neutrophilic inflammation and mucosal disease by upregulating DEL-1. JCI Insight. 2020 Aug 6;5(15):e136706. doi: 10.1172/jci.insight.136706. PMID: 32603314; PMCID: PMC7455085.
1: Lu X, Tian Y, Lian X, Jin Y, Jin T, Zhao Q, Hu B, Shen X, Fan X. Integrated systems toxicology approaches identified the possible involvement of ABC transporters pathway in erythromycin estolate-induced liver injury in rat. Food Chem Toxicol. 2014 Mar;65:343-55. doi: 10.1016/j.fct.2013.12.050. Epub 2014 Jan 10. PubMed PMID: 24412560. 2: Lakritz J, Wilson WD, Marsh AE, Mihalyi JE. Pharmacokinetics of erythromycin estolate and erythromycin phosphate after intragastric administration to healthy foals. Am J Vet Res. 2000 Aug;61(8):914-9. PubMed PMID: 10951982. 3: 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. PubMed PMID: 3259856; PubMed Central PMCID: PMC172220. 4: 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. PubMed PMID: 3142349; PubMed Central PMCID: PMC172382. 5: Venkateswaran S, Pari L, Viswanathan P, Menon VP. Protective effect of Livex, a herbal formulation against erythromycin estolate induced hepatotoxicity in rats. J Ethnopharmacol. 1997 Aug;57(3):161-7. PubMed PMID: 9292408. 6: Pari L, Murugan P. Protective role of tetrahydrocurcumin against erythromycin estolate-induced hepatotoxicity. Pharmacol Res. 2004 May;49(5):481-6. PubMed PMID: 14998559. 7: Stubbs C, Kanfer I. Variability in the absorption and disposition of erythromycin estolate in humans. J Pharm Sci. 1989 Aug;78(8):635-8. PubMed PMID: 2778669. 8: Potthast H, Schug B, Elze M, Schwerdtle R, Blume H. [Comparison of the bioavailabilities of erythromycin estolate and erythromycin ethylsuccinate dry suspension preparations in steady state]. Pharmazie. 1995 Jan;50(1):56-60. German. PubMed PMID: 7886126. 9: Richelmi P, Baldi C, Manzo L, Berte F, Martino AP, Mirabelli F, Bellomo G. Erythromycin estolate impairs the mitochondrial and microsomal calcium homeostasis: correlation with hepatotoxicity. Arch Toxicol Suppl. 1984;7:298-302. PubMed PMID: 6595996. 10: 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. PubMed PMID: 1565532. 11: 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. PubMed PMID: 6975059; PubMed Central PMCID: PMC181514. 12: DiSanto AR, Tserng KY, Chodos DJ, DeSante KA, Albert KS, Wagner JG. Comparative bioavailability evaluation of erythromycin base and its salts and esters. I. Erythromycin estolate capsules versus enteric-coated erythromycin base tablets. J Clin Pharmacol. 1980 Jul;20(7):437-43. PubMed PMID: 7430412. 13: 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. PubMed PMID: 6372437. 14: Adam D, Scholz H. Five days of erythromycin estolate versus ten days of penicillin V in the treatment of group A streptococcal tonsillopharyngitis in children. Pharyngitis Study Group. Eur J Clin Microbiol Infect Dis. 1996 Sep;15(9):712-7. PubMed PMID: 8922570. 15: Welling PG, Elliott RL, Pitterle ME, Corrick-West HP, Lyons LL. Plasma levels following single and repeated doses of erythromycin estolate and erythromycin stearate. J Pharm Sci. 1979 Feb;68(2):150-5. PubMed PMID: 423080. 16: Brown ST, Pedersen HB, Holmes KK. Comparison of erythromycin base and estolate in gonococcal urethritis. JAMA. 1977 Sep 26;238(13):1371-3. PubMed PMID: 408522. 17: Pari L, Uma A. Protective effect of Sesbania grandiflora against erythromycin estolate-induced hepatotoxicity. Therapie. 2003 Sep-Oct;58(5):439-43. PubMed PMID: 14682193. 18: Cachet T, Delrue M, Paesen J, Busson R, Roets E, Hoogmartens J. Analysis of erythromycin estolate by liquid chromatography. J Pharm Biomed Anal. 1992 Oct-Dec;10(10-12):851-60. PubMed PMID: 1298393. 19: Gaeta GB, Utili R, Adinolfi LE, Abernathy CO, Giusti G. Characterization of the effects of erythromycin estolate and erythromycin base on the excretory function of the isolated rat liver. Toxicol Appl Pharmacol. 1985 Sep 15;80(2):185-92. PubMed PMID: 2992120. 20: Keeffe EB, Reis TC, Berland JE. Hepatotoxicity to both erythromycin estolate and erythromycin ethylsuccinate. Dig Dis Sci. 1982 Aug;27(8):701-4. PubMed PMID: 6980110.