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    Erythromycin Ethylsuccinate

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 1264-62-6, Erythroped, Pediamycin, Eryped, Wyamycin e, Erythromycin ethyl succinate
    Molecular Formula
    C43H75NO16
    Molecular Weight
    862.1  g/mol
    InChI Key
    NSYZCCDSJNWWJL-YXOIYICCSA-N
    FDA UNII
    1014KSJ86F
    A macrolide antibiotic, produced by Streptomyces erythreus. This compound is an ester of erythromycin base and succinic acid. It acts primarily as a bacteriostatic agent. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-O-[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] 1-O-ethyl butanedioate
    2.1.2 InChI
    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/t22-,23-,24+,25+,26-,27+,28+,29-,32+,34+,35-,36-,37+,38-,40+,41-,42-,43-/m1/s1
    2.1.3 InChI Key
    NSYZCCDSJNWWJL-YXOIYICCSA-N
    2.1.4 Canonical SMILES
    CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)OC(=O)CCC(=O)OCC)(C)O)C)C)O)(C)O
    2.1.5 Isomeric SMILES
    CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)OC(=O)CCC(=O)OCC)(C)O)C)C)O)(C)O
    2.2 Other Identifiers
    2.2.1 UNII
    1014KSJ86F
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. E-mycin E

    2. Emycin E

    3. Eryped

    4. Erythroped

    5. Ethyl Succinate, Eyrthromycin

    6. Ethylsuccinate, Erythromycin

    7. Eyrthromycin Ethyl Succinate

    8. Monomycin

    9. Pediamycin

    10. Succinate, Eyrthromycin Ethyl

    11. Wyamycin E

    2.3.2 Depositor-Supplied Synonyms

    1. 1264-62-6

    2. Erythroped

    3. Pediamycin

    4. Eryped

    5. Wyamycin E

    6. Erythromycin Ethyl Succinate

    7. Erythromycin, 2'-(ethyl Butanedioate)

    8. Wyamycin

    9. Erythromycin 2'-(ethyl Butanedioate)

    10. E.e.s.

    11. Mls001074901

    12. 41342-53-4

    13. Nsc-756758

    14. Erythromycin-ethyl Succinate

    15. Succinic Acid, Monoethyl Ester, Monoester With Erythromycin

    16. Chebi:31555

    17. Erythrocin Ethyl Succinate

    18. 1014ksj86f

    19. E-mycin E

    20. Smr000058868

    21. Erythromycin 2'-(ethyl Succinate)

    22. Anamycin

    23. Arpimycin

    24. Ery-ped

    25. Pediamycin 400

    26. Ees Granules

    27. E.e.s

    28. Erythromycin, Ethyl Succinate

    29. Ees (antiobiotic)

    30. Hsdb 3075

    31. Erythromycin Ethylsuccinate [jan]

    32. Erythromycin, Mono(ethyl Succinate)

    33. Einecs 215-033-8

    34. Brn 0077638

    35. Esinol

    36. Unii-1014ksj86f

    37. Erythromycin, Mono(ethyl Succinate) (ester)

    38. Ncgc00183038-01

    39. E-mycin-e

    40. E.e.s 200

    41. E.e.s 400

    42. Eryped (tn)

    43. Durapaediat

    44. Eryliquid

    45. Refkas

    46. Erythrocin W (tn)

    47. Erythromycin Ethylsuccinate [usp:jan]

    48. Spectrum_001046

    49. Spectrum2_000983

    50. Spectrum3_000419

    51. Spectrum4_000536

    52. Spectrum5_000668

    53. Erythromycin-ethylsuccinate

    54. Dsstox_cid_2993

    55. Dsstox_rid_76821

    56. Dsstox_gsid_22993

    57. Erythromycin A Ethylsuccinate

    58. Schembl18259

    59. Bspbio_001978

    60. Kbiogr_001171

    61. Kbioss_001526

    62. 4-18-00-07416 (beilstein Handbook Reference)

    63. Mls000028651

    64. Mls001076672

    65. Succinicacid,monoethylester,monoesterwitherythromycin

    66. Divk1c_000764

    67. Spectrum1500279

    68. Spbio_001045

    69. Cid_443953

    70. Chembl1200688

    71. Dtxsid4022993

    72. Bdbm96262

    73. E.e.s. (tn)

    74. Hms502g06

    75. Kbio1_000764

    76. Kbio2_001526

    77. Kbio2_004094

    78. Kbio2_006662

    79. Kbio3_001198

    80. Ninds_000764

    81. Sterile Erythromycin Ethylsuccinate

    82. Hms1923i21

    83. Hms2091d03

    84. Pharmakon1600-01500279

    85. Erithromycin Ethyl Succinate

    86. Hy-b0957

    87. 2'-(ethyl Butanedioate)erythromycin

    88. Tox21_113497

    89. Ccg-40201

    90. Lmpk05000001

    91. Mfcd00084692

    92. Nsc756758

    93. S4060

    94. Akos008145410

    95. Zinc169356230

    96. Cs-4434

    97. Nsc 756758

    98. Erythromycin Ethylsuccinate (jp17/usp)

    99. Erythromycin Ethylsuccinate [mi]

    100. Idi1_000764

    101. Erythromycin (as Ethyl Succinate)

    102. Ncgc00021382-03

    103. 4-o-[(2s,3r,4s,6r)-4-(dimethylamino)-2-[[(3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] 1-o-ethyl Butanedioate

    104. Erythromycin Ethylsuccinate [hsdb]

    105. Cas-1264-62-6

    106. Erythromycin Ethylsuccinate [vandf]

    107. Sbi-0051367.p003

    108. Erythromycin Ethylsuccinate [usp-rs]

    109. Erythromycin Ethylsuccinate [who-dd]

    110. Erythromycin Ethylsuccinate [who-ip]

    111. Erythromycin Ethyl Succinate [mart.]

    112. D01361

    113. Ab00051980_11

    114. Ab00051980_12

    115. Erythromycin Ethylsuccinate [orange Book]

    116. A805556

    117. Erythromycin Ethylsuccinate [ep Monograph]

    118. Erythromycin Ethylsuccinate [usp Monograph]

    119. Erythromycini Ethylsuccinas [who-ip Latin]

    120. Sr-05000001617

    121. Eryzole Component Erythromycin Ethylsuccinate

    122. Sr-05000001617-1

    123. Erythromycin Ethylsuccinate Component Of Eryzole

    124. Pediazole Component Erythromycin Ethylsuccinate

    125. Q27114406

    126. Erythromycin Ethylsuccinate Component Of Pediazole

    127. Erythromycin Ethylsuccinate For Impurity P Identification

    128. Sterile Erythromycin Ethylsuccinate [usp Monograph]

    129. Oxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] 1-o-ethyl Butanedioate

    130. (2s,3r,4s,6r)-4-(dimethylamino)-2-(((3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-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-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyltetrahydro-2h-pyran-3-yl Ethyl Succinate

    131. (3r*,4s*,5s*,6r*,7r*,9r*,11r*,12r*,13s*,14r*)-4-((2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-((2- Ethyl Butanedioate -3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyl)oxy)oxacyclotetradecane-2,10-dione

    132. 4-o-[(2s,3r,4s,6r)-4-(dimethylamino)-2-[[(3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-2,10-di

    133. O4-[(2s,3r,4s,6r)-4-(dimethylamino)-2-[[(3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyl-tetrahydropyran-3-yl] O1-ethyl Butanedioate

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 862.1 g/mol
    Molecular Formula C43H75NO16
    XLogP33.4
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count14
    Exact Mass861.50858530 g/mol
    Monoisotopic Mass861.50858530 g/mol
    Topological Polar Surface Area226 Ų
    Heavy Atom Count60
    Formal Charge0
    Complexity1450
    Isotope Atom Count0
    Defined Atom Stereocenter Count18
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 12  
    Drug NameE.e.s. 200
    Active IngredientErythromycin ethylsuccinate
    Dosage FormSuspension
    RouteOral
    Strengtheq 200mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    2 of 12  
    Drug NameE.e.s. 400
    Active IngredientErythromycin ethylsuccinate
    Dosage FormTablet; Suspension
    RouteOral
    Strengtheq 400mg base/5ml; eq 400mg base
    Market StatusPrescription
    CompanyArbor Pharms

    3 of 12  
    Drug NameEryped
    Active IngredientErythromycin ethylsuccinate
    Dosage FormGranule
    RouteOral
    Strengtheq 400mg base/5ml; eq 200mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    4 of 12  
    Drug NameErythromycin ethylsuccinate
    Drug LabelErythromycin is produced by a strain of Saccharopolyspora erythraea (formerly Streptomyces erythraeus) and belongs to the macrolide group of antibiotics. It is basic and readily forms salts with acids. The base, the stearate salt, and the esters are...
    Active IngredientErythromycin ethylsuccinate
    Dosage FormTablet
    RouteOral
    Strengtheq 400mg base
    Market StatusPrescription
    CompanyArbor Pharms

    5 of 12  
    Drug NamePediamycin
    Active IngredientErythromycin ethylsuccinate
    Dosage FormSuspension
    RouteOral
    Strengtheq 200mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    6 of 12  
    Drug NamePediamycin 400
    Active IngredientErythromycin ethylsuccinate
    Dosage FormSuspension
    RouteOral
    Strengtheq 400mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    7 of 12  
    Drug NameE.e.s. 200
    Active IngredientErythromycin ethylsuccinate
    Dosage FormSuspension
    RouteOral
    Strengtheq 200mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    8 of 12  
    Drug NameE.e.s. 400
    Active IngredientErythromycin ethylsuccinate
    Dosage FormTablet; Suspension
    RouteOral
    Strengtheq 400mg base/5ml; eq 400mg base
    Market StatusPrescription
    CompanyArbor Pharms

    9 of 12  
    Drug NameEryped
    Active IngredientErythromycin ethylsuccinate
    Dosage FormGranule
    RouteOral
    Strengtheq 400mg base/5ml; eq 200mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    10 of 12  
    Drug NameErythromycin ethylsuccinate
    Drug LabelErythromycin is produced by a strain of Saccharopolyspora erythraea (formerly Streptomyces erythraeus) and belongs to the macrolide group of antibiotics. It is basic and readily forms salts with acids. The base, the stearate salt, and the esters are...
    Active IngredientErythromycin ethylsuccinate
    Dosage FormTablet
    RouteOral
    Strengtheq 400mg base
    Market StatusPrescription
    CompanyArbor Pharms

    11 of 12  
    Drug NamePediamycin
    Active IngredientErythromycin ethylsuccinate
    Dosage FormSuspension
    RouteOral
    Strengtheq 200mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    12 of 12  
    Drug NamePediamycin 400
    Active IngredientErythromycin ethylsuccinate
    Dosage FormSuspension
    RouteOral
    Strengtheq 400mg base/5ml
    Market StatusPrescription
    CompanyArbor Pharms

    4.2 Therapeutic Uses

    Antibiotics, Macrolide; Enzyme Inhibitors; Gastrointestinal Agents; Protein Synthesis Inhibitors

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    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.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1123

    ERYTHROMYCIN IS...ANTIMICROBIAL... ERYTHROMYCIN IS.../ACTIVE/ AGAINST MOST GRAM-POSITIVE BACTERIA, MANY ANAEROBES...& LEGIONNAIRE'S BACILLUS. /ERYTHROMYCIN/

    Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 55

    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/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1224

    A REVIEW OF THE ANTIMICROBIAL SPECTRUM, PHARMACOLOGY & THERAPEUTIC USE OF ERYTHROMYCIN & ITS DERIVATIVES. (REF 24).

    MEADE RH; DRUG THERAPY REVIEWS; ANTIMICROBIAL SPECTRUM, PHARMACOLOGY & THERAPEUTIC USE OF ERYTHROMYCIN & ITS DERIVATIVES; AM J HOSP PHARM 36, SEPT 1979, 1185-1189

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Gastrointestinal Agents

    Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Protein Synthesis Inhibitors

    Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Macrolide Antimicrobial [EPC]; Macrolide [EPC]; Macrolides [CS]; Decreased Sebaceous Gland Activity [PE]
    5.3 Absorption, Distribution and Excretion

    ERYTHROMYCIN ETHYLSUCCINATE IS PARTIALLY DISSOCIATED IN INTESTINE; BOTH ERYTHROMYCIN & UNDISSOCIATED ESTER ARE ABSORBED &, IN THE BLOOD, THE ESTER IS HYDROLYZED TO RELEASE FREE ERYTHROMYCIN.

    Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 54

    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.

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1223

    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.

    CHELVAN P ET AL; BILIARY EXCRETION OF ERYTHROMYCIN AFTER PARENTERAL ADMINISTRATION; BR J CLIN PHARMACOL 8(3) 233 (1979)

    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.

    SIMON C; CURR MED RES OPIN 6(8) 17 (1980)