Erythromycin | CAS#114-07-8 | protein translation inhibitor | mammalian mRNA splicing inhibitor

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

MedKoo CAT#: 540123

CAS#: 114-07-8

Description: Erythromycin is an inhibitor of protein translation and mammalian mRNA splicing. It inhibits growth of gram negative and gram positiove bacteria.

Chemical Structure

Erythromycin

CAS# 114-07-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540123
Name: Erythromycin
CAS#: 114-07-8
Chemical Formula: C37H67NO13
Exact Mass: 733.46
Molecular Weight: 733.930
Elemental Analysis: C, 60.55; H, 9.20; N, 1.91; O, 28.34

Price and Availability

Size	Price	Availability
5g	USD 250	2 weeks
10g	USD 400	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 41342-53-4(Ethylsuccinate) 7704-67-8(Thiocyanate)

Synonym: Emycin; HSDB 3074; HSDB-3074; HSDB3074; Eryc-125; Eryc-250; Erythromycin

IUPAC/Chemical Name: (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-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione

InChi Key: ULGZDMOVFRHVEP-RWJQBGPGSA-N

InChi Code: 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

SMILES Code: C[C@@H]([C@@H]([C@H](C(O[C@@H]([C@@]([C@H](O)[C@@H](C)C1=O)(C)O)CC)=O)C)O[C@H]2C[C@]([C@@H](O)[C@H](C)O2)(OC)C)[C@H]([C@](C)(O)C[C@H]1C)O[C@H](O[C@@H](C[C@@H]3N(C)C)C)[C@@H]3O

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: >2 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

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Product Data:

Product Data

Instruction:

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Biological target:	Erythromycin acts by binding to bacterial 50S ribosomal subunits and inhibits RNA-dependent protein synthesis by blockage of transpeptidation and/or translocation reactions, without affecting synthesis of nucleic acid.
In vitro activity:	The Th17 cells in the CSE-exposed DC/MLR group increased significantly compared with those in the control DC/MLR group (P < 0.05). Moreover, Th17 cells in the CD40-blocked CSE-exposed DC/MLR group and EM-treated CSE-exposed DC/MLR group were reduced compared with those in the CSE-exposed DC/MLR group (P < 0.05). Thus, these findings suggested that EM suppressed the CSE-exposed DC-mediated polarization of CD4+ T cells into Th17 cells and that this effect may be mediated through inhibition of the CD40/CD40L pathway. Reference: J Immunol Res. 2020; 2020: 1387952. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7201779/
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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	15.0	20.44
	Ethanol	88.5	120.58
	Ethanol:PBS (pH 7.2) (1:1)	0.5	0.68
	Water	2.0	2.73

Preparing Stock Solutions

The following data is based on the product molecular weight 733.93 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.

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. 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. 2. Zhang H, Qiu SL, Tang QY, Zhou X, Zhang JQ, He ZY, Bai J, Li MH, Deng JM, Liang Y, Zhong XN. Erythromycin suppresses neutrophil extracellular traps in smoking-related chronic pulmonary inflammation. Cell Death Dis. 2019 Sep 12;10(9):678. doi: 10.1038/s41419-019-1909-2. PMID: 31515489; PMCID: PMC6742640. 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. 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. 2. Zhang H, Qiu SL, Tang QY, Zhou X, Zhang JQ, He ZY, Bai J, Li MH, Deng JM, Liang Y, Zhong XN. Erythromycin suppresses neutrophil extracellular traps in smoking-related chronic pulmonary inflammation. Cell Death Dis. 2019 Sep 12;10(9):678. doi: 10.1038/s41419-019-1909-2. PMID: 31515489; PMCID: PMC6742640.
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.

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1: Krasniqi S, Matzneller P, Kinzig M, Sörgel F, Hüttner S, Lackner E, Müller M, Zeitlinger M. Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. doi: 10.1128/AAC.05490-11. Epub 2011 Nov 14. PubMed PMID: 22083477; PubMed Central PMCID: PMC3264267.

2: Liang JH, Han X. Structure-activity relationships and mechanism of action of macrolides derived from erythromycin as antibacterial agents. Curr Top Med Chem. 2013;13(24):3131-64. Review. PubMed PMID: 24200358.

3: Li X, Ma S, Yan M, Wang Y, Ma S. Synthesis and antibacterial evaluation of novel 11,4″-disubstituted azithromycin analogs with greatly improved activity against erythromycin-resistant bacteria. Eur J Med Chem. 2013 Jan;59:209-17. doi: 10.1016/j.ejmech.2012.11.028. Epub 2012 Nov 24. PubMed PMID: 23229056.

4: Vendrell D, Serarols L, Balcázar JL, de Blas I, Gironés O, Múzquiz JL, Ruiz-Zarzuela I. Accumulation and depletion kinetics of erythromycin in rainbow trout (Oncorhynchus mykiss). Prev Vet Med. 2012 Jun 1;105(1-2):160-3. doi: 10.1016/j.prevetmed.2012.02.017. Epub 2012 Mar 20. PubMed PMID: 22436556.

5: Carreras C, Frykman S, Ou S, Cadapan L, Zavala S, Woo E, Leaf T, Carney J, Burlingame M, Patel S, Ashley G, Licari P. Saccharopolyspora erythraea-catalyzed bioconversion of 6-deoxyerythronolide B analogs for production of novel erythromycins. J Biotechnol. 2002 Jan 18;92(3):217-28. PubMed PMID: 11689246.

6: Amsden GW. Erythromycin, clarithromycin, and azithromycin: are the differences real? Clin Ther. 1996 Jan-Feb;18(1):56-72; discussion 55. Review. PubMed PMID: 8851453.

7: Brittain DC. Erythromycin. Med Clin North Am. 1987 Nov;71(6):1147-54. Review. PubMed PMID: 3320616.

8: Morimoto S, Misawa Y, Adachi T, Nagate T, Watanabe Y, Omura S. Chemical modification of erythromycins. II. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A. J Antibiot (Tokyo). 1990 Mar;43(3):286-94. PubMed PMID: 2324013.

9: Tuominen RK, Lehtinen R, Peltola J, Wikberg R, Gordin A, Kokkonen P, Pohto P. Penetration of erythromycin into periapical lesions after repeated doses of erythromycin acistrate and erythromycin stearate: a pilot study. Oral Surg Oral Med Oral Pathol. 1991 Jun;71(6):684-8. PubMed PMID: 2062521.

10: Lehtonen L, Wikberg R, Karhunen M, Kokkonen P, Tuominen R. Erythromycin and 2'-acetyl erythromycin concentrations in plasma and pelvic tissues after repeated doses of erythromycin acistrate. Arzneimittelforschung. 1993 Jan;43(1):53-6. PubMed PMID: 8447849.

11: Basu SK, Manna PK, Goswami BB. Studies on the intravenous pharmacokinetics in rabbit and in vitro protein binding of two new salts of erythromycin: erythromycin maltobionate and erythromycin fumarate. Biopharm Drug Dispos. 1992 Aug;13(6):437-43. PubMed PMID: 1391680.

12: Bansal BK, Bajwa NS, Randhawa SS, Ranjan R, Dhaliwal PS. Elimination of erythromycin in milk after intramammary administration in cows with specific mastitis: relation to dose, milking frequency and udder health. Trop Anim Health Prod. 2011 Feb;43(2):323-9. doi: 10.1007/s11250-010-9692-1. Epub 2010 Sep 16. PubMed PMID: 20844949.

13: 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.

14: Alexander RE, Grogan DM. Long-acting erythromycins: assessing their role in treating outpatient odontogenic infections. Tex Dent J. 2009 Apr;126(4):326-33. Review. Erratum in: Tex Dent J. 2009 May;126(5):383. PubMed PMID: 19472551.

15: Samra Z, Rosenberg S, Dan M. Susceptibility of Ureaplasma urealyticum to tetracycline, doxycycline, erythromycin, roxithromycin, clarithromycin, azithromycin, levofloxacin and moxifloxacin. J Chemother. 2011 Apr;23(2):77-9. PubMed PMID: 21571622.

16: Alvarez-Elcoro S, Enzler MJ. The macrolides: erythromycin, clarithromycin, and azithromycin. Mayo Clin Proc. 1999 Jun;74(6):613-34. Review. PubMed PMID: 10377939.

17: McGimpsey JG, Webb CH, McCrea PH. Comparison of serum erythromycin concentration following administration of 100 mg erythromycin ethyl succinate intramuscularly and 500 mg erythromycin stearate orally. Int J Oral Surg. 1981;10(Suppl 1):198-202. PubMed PMID: 6807878.

18: Tamm M, Todisco T, Feldman C, Garbino J, Blasi F, Hogan P, de Caprariis PJ, Hoepelman IM. Clinical and bacteriological outcomes in hospitalised patients with community-acquired pneumonia treated with azithromycin plus ceftriaxone, or ceftriaxone plus clarithromycin or erythromycin: a prospective, randomised, multicentre study. Clin Microbiol Infect. 2007 Feb;13(2):162-71. PubMed PMID: 17328728.

19: 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.

20: 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.

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