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DSSTox_CID_2993

DSSTox_CID_2993

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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

DSSTox_CID_2993

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 Formula	C₄₃H₇₅NO₁₆
Molecular Weight	862.1 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	14
Exact Mass	861.50858530 g/mol
Monoisotopic Mass	861.50858530 g/mol
Topological Polar Surface Area	226 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	1450
Isotope Atom Count	0
Defined Atom Stereocenter Count	18
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 12
Drug Name	E.e.s. 200
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Suspension
Route	Oral
Strength	eq 200mg base/5ml
Market Status	Prescription
Company	Arbor Pharms

2 of 12
Drug Name	E.e.s. 400
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Tablet; Suspension
Route	Oral
Strength	eq 400mg base/5ml; eq 400mg base
Market Status	Prescription
Company	Arbor Pharms

3 of 12
Drug Name	Eryped
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Granule
Route	Oral
Strength	eq 400mg base/5ml; eq 200mg base/5ml
Market Status	Prescription
Company	Arbor Pharms

4 of 12
Drug Name	Erythromycin ethylsuccinate
Drug Label	Erythromycin 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 Ingredient	Erythromycin ethylsuccinate
Dosage Form	Tablet
Route	Oral
Strength	eq 400mg base
Market Status	Prescription
Company	Arbor Pharms

5 of 12
Drug Name	Pediamycin
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Suspension
Route	Oral
Strength	eq 200mg base/5ml
Market Status	Prescription
Company	Arbor Pharms

6 of 12
Drug Name	Pediamycin 400
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Suspension
Route	Oral
Strength	eq 400mg base/5ml
Market Status	Prescription
Company	Arbor Pharms

7 of 12
Drug Name	E.e.s. 200
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Suspension
Route	Oral
Strength	eq 200mg base/5ml
Market Status	Prescription
Company	Arbor Pharms

8 of 12
Drug Name	E.e.s. 400
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Tablet; Suspension
Route	Oral
Strength	eq 400mg base/5ml; eq 400mg base
Market Status	Prescription
Company	Arbor Pharms

9 of 12
Drug Name	Eryped
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Granule
Route	Oral
Strength	eq 400mg base/5ml; eq 200mg base/5ml
Market Status	Prescription
Company	Arbor Pharms

10 of 12
Drug Name	Erythromycin ethylsuccinate
Drug Label	Erythromycin 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 Ingredient	Erythromycin ethylsuccinate
Dosage Form	Tablet
Route	Oral
Strength	eq 400mg base
Market Status	Prescription
Company	Arbor Pharms

11 of 12
Drug Name	Pediamycin
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Suspension
Route	Oral
Strength	eq 200mg base/5ml
Market Status	Prescription
Company	Arbor Pharms

12 of 12
Drug Name	Pediamycin 400
Active Ingredient	Erythromycin ethylsuccinate
Dosage Form	Suspension
Route	Oral
Strength	eq 400mg base/5ml
Market Status	Prescription
Company	Arbor 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)

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