Erythromycin hydrochloride

• CAT Number: I026998
• CAS Number: 14271-02-4
• Molecular Formula: C37H68ClNO13
• Molecular Weight: 770.39
• Purity: 98%
• Synonyms: Erythromycin hydrochloride; Erythromycin HCl; Ilotycin hydrochloride; Ilotycin HCl
• Solubility: To be determined
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC 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 hydrochloride
• InChI: 1S/C37H67NO13.ClH/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;1H/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;/m1./s1
• InChIKey: BXBSPTIDIMGJNO-YZPBMOCRSA-N
• SMILES: Cl.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O

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

Reference

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.