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Erythromycin Estolate

Synopsis, Chemistry

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Also known as: Ilosone, 3521-62-8, Lauromicina, Erythromycin propionate lauryl sulfate, Marcoeritrex, Stellamicina

Molecular Formula

C₅₂H₉₇NO₁₈S

Molecular Weight

1056.4 g/mol

InChI Key

AWMFUEJKWXESNL-JZBHMOKNSA-N

FDA UNII

XRJ2P631HP

A macrolide antibiotic, produced by Streptomyces erythreus. It is the lauryl sulfate salt of the propionic ester of erythromycin. This erythromycin salt 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

Erythromycin Estolate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(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] propanoate;dodecyl hydrogen sulfate

2.1.2 InChI

InChI=1S/C40H71NO14.C12H26O4S/c1-15-27-40(11,48)33(44)22(5)30(43)20(3)18-38(9,47)35(55-37-32(53-28(42)16-2)26(41(12)13)17-21(4)50-37)23(6)31(24(7)36(46)52-27)54-29-19-39(10,49-14)34(45)25(8)51-29;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h20-27,29,31-35,37,44-45,47-48H,15-19H2,1-14H3;2-12H2,1H3,(H,13,14,15)/t20-,21-,22+,23+,24-,25+,26+,27-,29+,31+,32-,33-,34+,35-,37+,38-,39-,40-;/m1./s1

2.1.3 InChI Key

AWMFUEJKWXESNL-JZBHMOKNSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCOS(=O)(=O)O.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)CC)(C)O)C)C)O)(C)O

2.1.5 Isomeric SMILES

CCCCCCCCCCCCOS(=O)(=O)O.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)CC)(C)O)C)C)O)(C)O

2.2 Other Identifiers

2.2.1 UNII

XRJ2P631HP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Eromycin

2. Erythromycin Propionate Dodecyl Sulfate

3. Erythromycin Propionate Lauryl Sulfate

4. Erythromycin Propionate Monododecyl Sulfate

5. Estolate, Erythromycin

6. Ilosone

7. Lauromicina

2.3.2 Depositor-Supplied Synonyms

1. Ilosone

2. 3521-62-8

3. Lauromicina

4. Erythromycin Propionate Lauryl Sulfate

5. Marcoeritrex

6. Stellamicina

7. Eritroger

8. Estomicina

9. Roxomicina

10. Neo-erycinum

11. Erythromycin Estorate

12. Pels

13. Eromycin

14. Biomicron

15. Eriscel

16. Propionylerythromycin Lauryl Sulfate

17. Erythromycin (as Estolate)

18. Erythromycin 2'-propionate Dodecyl Sulfate (salt)

19. Xrj2p631hp

20. Erythromycin, 2'-propanoate, Dodecyl Sulfate (salt)

21. Prospiocine

22. Erytrarco

23. Lauryl Sulfate Propionyl Erythromycin Ester

24. Chebi:4846

25. Ery-toxinal Dodecylsulfate

26. Erythromycinestolate

27. Erythromycin Propionate, Compound With Dodecyl Sulfate

28. Nsc-263364

29. Lubomycine B

30. Erythromycin Estorate (jan)

31. Erythromycin Propionate Dodecylsulfate (salt)

32. Erythromycin 5-(3-propionate) Dodecyl Sulfate

33. Erythromycin Estorate [jan]

34. Erythromycine Estolate

35. Erythromycin Propionyl Laurylsulfate

36. Erythromycin Propionate, Compd. With Dodecyl Sulfate

37. Unii-xrj2p631hp

38. Einecs 222-532-4

39. Ilosone (tn)

40. Nsc 263364

41. Erythromycin Estolate [usan:usp:ban:jan]

42. Schembl3331

43. Dsstox_cid_17224

44. Dsstox_rid_79309

45. Dsstox_gsid_37224

46. Erythromycin Estolate (usp)

47. Spectrum1501176

48. Chembl2218877

49. Dtxsid1037224

50. Erythromycin, 2'-propionate, Monododecyl Sulfate (salt)

51. Bdbm31688

52. Hms500a11

53. Erythromycin Estolate [mi]

54. Hms1921n13

55. Hms2092j15

56. Pharmakon1600-01501176

57. Erythromycin, Propionate (ester), Compd. With Monododecyl Sulfate

58. Hy-n7121

59. Propionic Acid, 2'-ester With Erythromycin, Dodecyl Sulfate Salt

60. Erythromycin Estolate [usan]

61. Tox21_302229

62. Ccg-38968

63. Erythromycin Estolate [vandf]

64. Lmpk04000015

65. Mfcd00084691

66. Nsc757880

67. S5532

68. Erythromycin Estolate [mart.]

69. Monopropionylerythromycin Laurylsulfate

70. Akos015896121

71. Erythromycin Estolate [usp-rs]

72. Erythromycin Estolate [who-dd]

73. Nsc-757880

74. Sulfuric Acid, Monododecyl Ester, Compd. With Erythromycin 2'-propionate (1:1)

75. Ncgc00180881-01

76. Ncgc00180881-02

77. Ncgc00255571-01

78. Cas-3521-62-8

79. Erythromycin Estolate [orange Book]

80. Erythromycin 2''-propionate Dodecyl Sulfate

81. Erythromycin Estolate [ep Monograph]

82. Propionyl Erythromycin Lauryl Sulfate

83. Cs-0031228

84. Erythromycin Estolate [usp Monograph]

85. Erythromycin Lauryl Sulfate, Propionyl

86. C08031

87. D00851

88. D70256

89. 521e628

90. Sr-05000002085

91. Ilosone Sulfa Component Erythromycin Estolate

92. Q-201066

93. Sr-05000002085-1

94. Q27106503

95. Erythromycin Estolate Component Of Ilosone Sulfa

96. Erythromycin 2'-propionate Dodecyl Sulfate (salt).

97. Erythromycin 2'-propionate Dodecyl Sulphate (salt).

98. Propionic Acid, 2'-ester With Erythromycin, Dodecyl Sulfate

99. Erythromycin, 2'-propanoate, Dodecyl Sulphate (salt)

100. Erythromycin, Propionate (ester), Compd. With Monododecyl Sulfate (1:1)

101. Sulfuric Acid, Monododecyl Ester, Compd. With Erythromycin 2'-propanoate (1:1)

102. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-4-(2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-6-[3,4,6-trideoxy-3-(dimethylamino)-2-o-propanoyl-beta-d-xylo-hexopyranosyloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione Dodecyl Hydrogen Sulfate

103. [(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] Propanoate;dodecyl Hydrogen Sulfate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₅₂H₉₇NO₁₈S
Molecular Weight	1056.4 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	22
Exact Mass	1055.64263642 g/mol
Monoisotopic Mass	1055.64263642 g/mol
Topological Polar Surface Area	272 Å²
Heavy Atom Count	72
Formal Charge	0
Complexity	1550
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	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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

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.)

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.)