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E8755

Sigma-Aldrich

Erythromycin ethyl succinate

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About This Item

Empirical Formula (Hill Notation):
C43H75NO16
CAS Number:
1264-62-6
Molecular Weight:
862.05
EC Number:
215-033-8
MDL number:
MFCD00084692
UNSPSC Code:
51282328
PubChem Substance ID:
24894684
NACRES:
NA.85

biological source

microbial

form

solid

potency

≥780 μg per mg

color

white

solubility

ethanol: 50 mg/mL

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

protein synthesis | interferes

SMILES string

CCOC(=O)CCC(=O)OC1C(CC(C)OC1OC2C(C)C(OC3CC(C)(OC)C(O)C(C)O3)C(C)C(=O)OC(CC)C(C)(O)C(O)C(C)C(=O)C(C)CC2(C)O)N(C)C

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

InChI key

NSYZCCDSJNWWJL-UHFFFAOYSA-N

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General description

Chemical structure: macrolide

Application

Erythromycin ethyl succinate is used to study erythromycin-resistant Streptococcus pyogenes and Streptococcus pneumoniae. It has been used to study down-regulation of motilin receptors on rabbit colon myocytes and lethal mutations in outer membrane genes omsA and firA in Salmonella typhimurium.

Biochem/physiol Actions

Erythromycin inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site) by binding to the 50s subunit of the bacterial 70s rRNA complex.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Precautionary Statements

P261 - P280 - P342 + P311

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R Vuorio et al.
Journal of bacteriology, 174(22), 7090-7097 (1992-11-01)
We have previously identified the gene (the ssc gene) defective in the thermosensitive and antibiotic-supersusceptible outer membrane permeability mutant SS-C of Salmonella typhimurium and shown that this gene is analogous to the Escherichia coli gene firA (L. Hirvas, P. Koski
S D Bologna et al.
The Journal of pharmacology and experimental therapeutics, 266(2), 852-856 (1993-08-01)
Acutely, erythromycin stimulates colonic smooth muscle contraction via action on motilin receptors, but the effects of chronic erythromycin exposure are unknown. Thus contraction and motilin binding studies were performed on rabbit colonic smooth muscle after 2 weeks of oral erythromycin
K P Klugman et al.
The Journal of antimicrobial chemotherapy, 42(6), 729-734 (1999-03-03)
The susceptibility of 40 erythromycin-resistant isolates of Streptococcus pyogenes and 40 multiply-resistant isolates of Streptococcus pneumoniae to six macrolide antibiotics, representing 14-, 15- and 16-membered lactone ring structures, was tested. The genetic basis for macrolide resistance in the strains was
Y A Cho et al.
Die Pharmazie, 67(2), 124-130 (2012-04-20)
The effects of curcumin, a natural anti-cancer compound, on the bioavailability and pharmacokinetics of tamoxifen and its metabolite, 4-hydroxytamoxifen, were investigated in rats. Tamoxifen and curcumin interact with cytochrom P450 (CYP) enzymes and P-glycoprotein, and the increase in the use
J J Stewart et al.
Journal of clinical pharmacology, 40(4), 347-353 (2000-04-13)
Motion sickness and the antimotion sickness drugs scopolamine (SCP) and promethazine (PMZ) inhibit gastric emptying (GE). This study was conducted to determine if erythromycin would exert its well-known prokinetic effects in normal and motion-sick subjects given antimotion sickness drugs. Fifteen
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