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Also known as: 3847-29-8, 33h58i7glq, Erythromycin lactobionate (1:1) (salt), Erythromycin lactobionate [jan], Erythromycin. compd. with lactobionic acid, Einecs 223-348-7
Molecular Formula
C49H89NO25
Molecular Weight
1092.2  g/mol
InChI Key
NNRXCKZMQLFUPL-WBMZRJHASA-N
FDA UNII
33H58I7GLQ

Erythromycin Lactobionate
Erythromycin Lactobionate is the lactobionate salt form of erythromycin, a broad-spectrum, topical macrolide antibiotic with antibacterial activity. Erythromycin lactobionate diffuses through the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This prevents bacterial protein synthesis. Erythromycin lactobionate may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved.
1 2D Structure

Erythromycin Lactobionate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-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-oxacyclotetradecane-2,10-dione;(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid
2.1.2 InChI
InChI=1S/C37H67NO13.C12H22O12/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26;13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;3-10,12-20H,1-2H2,(H,21,22)/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;3-,4-,5+,6+,7-,8-,9-,10-,12+/m11/s1
2.1.3 InChI Key
NNRXCKZMQLFUPL-WBMZRJHASA-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)O)(C)O)C)C)O)(C)O.C(C1C(C(C(C(O1)OC(C(CO)O)C(C(C(=O)O)O)O)O)O)O)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)O)(C)O)C)C)O)(C)O.C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C(=O)O)O)O)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
33H58I7GLQ
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 3847-29-8

2. 33h58i7glq

3. Erythromycin Lactobionate (1:1) (salt)

4. Erythromycin Lactobionate [jan]

5. Erythromycin. Compd. With Lactobionic Acid

6. Einecs 223-348-7

7. Erythrocin Lactobionate Iv

8. Unii-33h58i7glq

9. Erythromycin Mono(4-o-beta-d-galactopyranosyl-d-gluconate) (salt)

10. Lactobionic Acid, Compd. With Erythromycin (1:1)

11. Erythromycin Lactobionate [usp:ban:jan]

12. Erythromycini Lactobionas

13. 4-o-beta-d-galactopyranosyl-d-gluconic Acid Compd. With Erythromycin

14. Schembl41566

15. Chembl1200506

16. Sterile Erythromycin Lactobionate

17. Hy-b0220a

18. Dtxsid801009322

19. Erythromycin, 4-o-beta-d-galactopyranosyl-d-gluconate (salt)

20. Erythromycin Lactobionate [mi]

21. Erythromycin Lactobionate (jp17/usp)

22. D-gluconic Acid, 4-o-.beta.-d-galactopyranosyl-, Compd. With Erythromycin (1:1)

23. D-gluconic Acid, 4-o-beta-d-galactopyranosyl-, Compd. With Erythromycin (1:1)

24. Erythromycin Lactobionate [mart.]

25. Erythromycin Lactobionate [vandf]

26. Erythromycin Lactobionate [usp-rs]

27. Erythromycin Lactobionate [who-dd]

28. Erythromycin Lactobionate [who-ip]

29. Cs-0009646

30. D02009

31. Erythromycin Lactobionate [ep Monograph]

32. Erythromycin Lactobionate [orange Book]

33. Erythromycin Lactobionate [usp Impurity]

34. Erythromycini Lactobionas [who-ip Latin]

35. Erythromycin, Lactobionate (1:1) (salt)

36. Q27256272

37. Sterile Erythromycin Lactobionate [usp Monograph]

38. Erythromycin, 4-o-beta-d-galactopyranosyl-d-gluconate (1:1)

39. Erythromycin Mono(4-o-.beta.-d-galactopyranosyl-d-gluconate) (salt)

40. Erythromycin 4-o-beta-d-galactopyranosyl-d-gluconate;erythromycin 4-o-beta-d-galactopyranosyl-d-gluconate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 1092.2 g/mol
Molecular Formula C49H89NO25
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count26
Rotatable Bond Count15
Exact Mass1091.57236732 g/mol
Monoisotopic Mass1091.57236732 g/mol
Topological Polar Surface Area412 Ų
Heavy Atom Count75
Formal Charge0
Complexity1580
Isotope Atom Count0
Defined Atom Stereocenter Count27
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
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.)


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Macrolide Antimicrobial [EPC]; Macrolide [EPC]; Macrolides [CS]; Decreased Sebaceous Gland Activity [PE]

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