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Home > Encyclopedia > Erythromycin ethyl succinate

Erythromycin ethyl succinate

pharmaceutical raw materials
Erythromycin ethyl succinate structure

Erythromycin ethyl succinate 

structure
  • CAS No:

    1264-62-6

  • Formula:

    C43H75NO16

  • Chemical Name:

    Erythromycin ethyl succinate

  • Synonyms:

    Erythromycin,2′-(ethyl butanedioate);Erythromycin,mono(ethyl succinate) (ester);Erythromycin ethyl succinate;Erythromycin,2′-(ethyl succinate);Succinic acid,ethyl ester,monoester with erythromycin;Oxacyclotetradecane,erythromycin deriv.;Erythrocin ethyl succinate;Pediamycin;Erythroped;Evesin;Eritrocina;Esinol;EryPed;Paediathrocin;Erythro ES;Wyamycin E;Sigapedil;Durapaediat;Eryliquid;EES;Arpimycin;Erythro-Holz;Refkas;Anamycin;E-Mycin e;Monomycin;1334-36-7;1386-36-3;7121-45-1;12125-46-1;22372-15-2;41342-53-4;68206-56-4;314725-13-8

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

ERYTHROMYCIN ETHYLSUCCINATE is crystals Erythromycin ethylsuccinate (EES, Pediamycin, EryPed) isthe ethylsuccinate mixed ester of erythromycin in which the2'-hydroxyl group of the desosamine is esterified. It isabsorbed as the ester and hydrolyzed slowly in the body toform erythromycin. It is somewhat acid labile, and itsabsorption is enhanced by the presence of food. The ester isinsoluble in water but soluble in alcohol and ether.


Butanedioic acid O4-[4-(dimethylamino)-2-[[14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyl-2-oxanyl)oxy]-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyl-3-oxanyl] ester O1-ethyl ester is an aminoglycoside.

Erythromycin ethyl succinate Basic Attributes

862.05

862.05

215-033-8

WHITE OR SLIGHTLY YELLOW, CRYSTALLINE POWDER

29419000

Characteristics

226

white

1.1417 (rough estimate)

109-110 °C

778.19°C (rough estimate)

>110°(230°F)

1.5280 (estimate)

Freely soluble in organic solvents, practically insoluble in water;ethanol: soluble 50mg/mL

2-8°C

LD50 oral in mouse: > 10gm/kg

ODORLESS OR PRACTICALLY SO

PRACTICALLY TASTELESS

PKA 7.1

Safety Information

2811

2

42/43-36/37/38

36-26

WM9800000

Xn,Xi

AFTER RECONSTITUTION OF COMMERCIALLY AVAILABLE POWDER, SUSPENSIONS ARE STABLE FOR 10 DAYS @ 2-8 °C

P261-P280-P284-P304 + P340-P342 + P311

H317-H334

|Danger|H317 (46.67%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P280, P285, P302+P352, P304+P341, P305+P351+P338, P321, P333+P313, P337+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 90 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Antibiotics, Macrolide; Enzyme Inhibitors; Gastrointestinal Agents; Protein Synthesis Inhibitors|RELATIVELY NONIRRITATING...& THUS IS WELL SUITED TO IM INJECTION. ...ITS ACTIONS & USES ARE ESSENTIALLY THOSE OF ERYTHROMYCIN...INTO WHICH IT IS CONVERTED IN THE BODY.|ERYTHROMYCIN IS...ANTIMICROBIAL... ERYTHROMYCIN IS.../ACTIVE/ AGAINST MOST GRAM-POSITIVE BACTERIA, MANY ANAEROBES...& LEGIONNAIRE'S BACILLUS. /ERYTHROMYCIN/|ERYTHROMYCIN MAY BE...BACTERIOSTATIC OR BACTERICIDAL DEPENDING ON NATURE OF MICROORGANISM & CONCN OF DRUG. ...MOST EFFECTIVE IN VITRO AGAINST GRAM-POSITIVE COCCI SUCH AS STAPHYLOCOCCUS AUREUS (PENICILLIN G SENSITIVE OR RESISTANT), GROUP A STREPTOCOCCI, ENTEROCOCCI & PNEUMOCOCCI; MANY GRAM-POSITIVE BACILLI... /ERYTHROMYCIN/|A REVIEW OF THE ANTIMICROBIAL SPECTRUM, PHARMACOLOGY & THERAPEUTIC USE OF ERYTHROMYCIN & ITS DERIVATIVES. (REF 24).

ERYTHROMYCIN ETHYLSUCCINATE IS PARTIALLY DISSOCIATED IN INTESTINE; BOTH ERYTHROMYCIN & UNDISSOCIATED ESTER ARE ABSORBED &, IN THE BLOOD, THE ESTER IS HYDROLYZED TO RELEASE FREE ERYTHROMYCIN.|ERYTHROMYCIN ETHYLSUCCINATE...IS ADEQUATELY ABSORBED FOLLOWING ORAL ADMINISTRATION, PARTICULARLY WHEN THE STOMACH IS EMPTY. PEAK CONCENTRATIONS IN PLASMA ARE 1.5 UG/ML (0.5 UG/ML OF BASE) 1 TO 2 HR AFTER ADMINISTRATION OF A 500 MG TABLET.|IN PATIENTS, MEAN BILE LEVELS OF ERYTHROMYCIN WERE APPROXIMATELY 10 TIMES HIGHER THAN CORRESPONDING SERUM CONCN 1 HR AFTER IV (ERYTHROMYCIN LACTOBIONATE) & IM (ERYTHROMYCIN SUCCINATE) INJECTION.|IN HEALTHY ADULT SUBJECTS & IN ADULT PATIENTS WITH BRONCHIAL INFECTIONS, PHARMACOKINETICS OF VARIOUS FORMULATIONS OF ERYTHROMYCIN WERE STUDIED. ERYTHROMYCIN ETHYLSUCCINATE WAS BETTER THAN ERYTHROMYCIN STEARATE FOR ORAL TREATMENT IN THAT IT WAS RAPIDLY & CONSISTENTLY ABSORBED.

AMONG HYPERSENSITIVITY REACTIONS ARE FEVER, EOSINOPHILIA, & SKIN ERUPTIONS, EACH OF WHICH MAY OCCUR ALONE OR IN COMBINATION; THEY DISAPPEAR SHORTLY AFTER THERAPY IS STOPPED. ...MAY PRODUCE IRRITATIVE EFFECTS. ORAL ADMIN...FREQUENTLY ACCOMPANIED BY EPIGASTRIC DISTRESS, WHICH MAY BE QUITE SEVERE. /ERYTHROMYCIN/|IM INJECTION OF QUANTITIES LARGER THAN 100 MG PRODUCES...SEVERE PAIN... PERSISTS FOR HR: IV PERFUSIONS OF 1-G DOSES...ALMOST REGULARLY IS FOLLOWED BY THROMBOPHLEBITIS. ...6 PT...DEVELOPED DIFFICULTY IN HEARING WHILE BEING TREATED WITH 4 G/DAY...IV. ... CESSATION...LED TO COMPLETE RETURN OF NORMAL HEARING... /ERYTHROMYCIN/|A CASE REPORT OF HEPATOTOXICITY RESULTING FROM ERYTHROMYCIN ETHYLSUCCINATE THERAPY IN 60-YR-OLD FEMALE IS DESCIRBED.

Erythromycin ethyl succinate Use and Manufacturing

Methods of Manufacturing

ERYTHROMYCIN IS ESTERIFIED AT THE 2' POSITION BY REACTING IT WITH ETHYL 3-CHLOROFORMYLPROPIONATE [CLCOCH2CH2CO2ET] IN DRY ACETONE IN THE PRESENCE OF SODIUM BICARBONATE.

Uses

antibacterial

PEDIAMYCIN (EES 400): TABLETS (CHEWABLE) 200 MG; GRANULES FOR DROPS (SUSPENSION) 100 MG/2.5 ML; GRANULES FOR SUSPENSION 200 MG/5 ML; SUSPENSION 200 MG/5 ML. ERYTHROCIN ETHYLSUCCINATE: INJECTION (SOLUTION) 50 MG/ML.

ERYTHROMYCIN ETHYLSUCCINATE INJECTION, USP (ERYTHROCIN ETHYLSUCCINATE-IM), CONTAINS 50 MG/ML IN 2- & 10-ML CONTAINERS FOR IM INJECTION. THIS PREPN INCL BUTYL AMINOBENZOATE (2%) AS LOCAL ANESTHETIC.|...USED IN FLAVORED ORAL "SUSPENSIONS" FOR PEDIATRIC USE.|...CONTAINS THE EQUIVALENT OF NOT LESS THAN 76.5% OF ERYTHROMYCIN BASE.|WHILE CROSS-RESISTANCE BETWEEN ERYTHROMYCIN & OTHER ANTIMICROBIAL AGENTS DOES NOT USUALLY OCCUR, IT HAS BEEN NOTED BETWEEN LINCOMYCIN & ERYTHROMYCIN IN STRAINS OF VIRIDANS GROUP OF STREPTOCOCCI ISOLATED FROM PT TREATED WITH EITHER AGENT. /ERYTHROMYCIN/|INCIDENCE OF ERYTHROMYCIN-RESISTANT STRAINS OF STAPH AUREUS HAS BEEN INCR; IN SOME HOSPITALS 50% OF STRAINS ARE NOT INHIBITED BY DRUG. OCCASIONAL STRAINS OF STREPTOCOCCUS PYOGENES & STREP (D) PNEUMONIAE RESISTANT TO DRUG HAVE BEEN RECOVERED FROM PT. /ERYTHROMYCIN/

ERYTHROMYCIN, ERYTHROMYCIN ESTOLATE, ERYTHROMYCIN ETHYL SUCCINATE & ERYTHROMYCIN STEARATE WERE DIFFERENTIATED BY THIN-LAYER CHROMATOGRAPHY.

FLUORIMETRIC DETERMINATION OF ERYTHROMYCIN ETHYLSUCCINATE IN SERUM BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIC & EXTRACTION METHOD. METHOD CAPABLE OF DETECTING LESS THAN 0.01 MUG/ML OF ERYTHROMYCIN & ERYTHROMYCINETHYLSUCCINATE.

Computed Properties

Molecular Weight:862.1
XLogP3:3.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:17
Rotatable Bond Count:14
Exact Mass:861.50858530
Monoisotopic Mass:861.50858530
Topological Polar Surface Area:226
Heavy Atom Count:60
Complexity:1450
Undefined Atom Stereocenter Count:18
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product belongs to the macrolide antibiotics, which is the ethyl succinate of erythromycin. It is more stable than erythromycin in gastric acid. It has antibacterial activity against Staphylococcus (except methicillin-resistant strains), various groups of streptococci and Gram-positive bacilli. Neisseria, Haemophilus influenzae, Bordetella pertussis, etc. are also sensitive to this product. This product also has antibacterial effects on various anaerobic bacteria except Bacteroides fragilis and Fusobacterium. It also has inhibitory effects on Legionella, Campylobacter fetus, some spirochetes, Mycoplasma pneumoniae, Rickettsia, Chlamydia and Chlamydia. This product is an antibacterial agent, but it also has a bactericidal effect on some bacteria at high concentrations. This product can penetrate the bacterial cell membrane and form a reversible bond with the 50S subunit of the bacterial ribosome near the donor site (P site), blocking the transfer RNA (t-RNA) from binding to the P site, and also blocking the displacement of the polypeptide chain from the acceptor site (A site) to the P site, thereby inhibiting bacterial protein synthesis.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • CENTURY PHARMACEUTICALS LTD

    United States United States
    Active
  • ALEMBIC PHARMACEUTICALS LTD

    United States United States
    Active
  • SOLARA A PHARMA SCIENCES LTD

    United States United States
    Active

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