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Merck
CN

45673

Sigma-Aldrich

Erythromycin

≥95.0% (NT)

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About This Item

Empirical Formula (Hill Notation):
C37H67NO13
CAS Number:
114-07-8
Molecular Weight:
733.93
Beilstein:
75279
EC Number:
204-040-1
MDL number:
MFCD00084654
UNSPSC Code:
51101500
PubChem Substance ID:
24869225

Key Documents

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Assay

≥95.0% (NT)

optical activity

[α]20/D −75±4°, c = 2% in ethanol

mp

133-135 °C

Mode of action

protein synthesis | interferes

SMILES string

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

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

InChI key

ULGZDMOVFRHVEP-RWJQBGPGSA-N

Gene Information

human ... ABCB1(5243), CYP3A4(1576), MLNR(2862)
mouse ... Abcb1a(18671), Abcb1b(18669)

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General description

Chemical structure: macrolide

Biochem/physiol Actions

Mode of Action: Erythromycin acts by inhibiting elongation at the transpeptidation step, specifically aminoacyl translocation from the A-site to P-site by binding to the 50s subunit of the bacterial 70s rRNA complex.

Antimicrobial Spectrum: This product acts against both gram-negative and gram-positive bacteria.

Other Notes

Inhibits bacterial protein synthesis by binding to the ribosomes; Inducible erythromycin resistance in bacteria

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
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H. Teraoka
Umschau in Wissenschaft Und Technik, 77, 347-347 (1977)
Inducible erythromycin resistance in bacteria.
B Weisblum
British medical bulletin, 40(1), 47-53 (1984-01-01)
Steven A Rogers et al.
Antimicrobial agents and chemotherapy, 54(5), 2112-2118 (2010-03-10)
2-aminoimidazoles are an emerging class of small molecules that possess the ability to inhibit and disperse biofilms across bacterial order, class, and phylum. Herein, we report the synergistic effect between a 2-aminoimidazole/triazole conjugate and antibiotics toward dispersing preestablished biofilms, culminating
Daniel Sherman et al.
Bioorganic & medicinal chemistry letters, 16(6), 1506-1509 (2006-01-03)
A new approach to 4''-substituted derivatives of erythromycin and clarithromycin was developed by converting them into corresponding 4''-malonic monoesters. Subsequent carbodiimide coupling with alcohols and amines provided new macrolide derivatives that are capable of binding to 50S ribosomal subunits and
Hong Yong et al.
Bioorganic & medicinal chemistry letters, 15(10), 2653-2658 (2005-05-03)
A novel series of 6-O-arylpropargyl diazalides was synthesized and evaluated for their antibacterial activity. Members of this series exhibited potent activity against erythromycin-resistant respiratory tract pathogens.
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