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Chemistry

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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 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 Formula	C₄₉H₈₉NO₂₅
Molecular Weight	1092.2 g/mol
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	26
Rotatable Bond Count	15
Exact Mass	1091.57236732 g/mol
Monoisotopic Mass	1091.57236732 g/mol
Topological Polar Surface Area	412 Å²
Heavy Atom Count	75
Formal Charge	0
Complexity	1580
Isotope Atom Count	0
Defined Atom Stereocenter Count	27
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.)

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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