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Erythromycin Stearate

Erythromycin Stearate

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Also known as: 643-22-1, Abboticine, Bristamycin, Erypar, Dowmycin e, Wyamycin s

Molecular Formula

C₅₅H₁₀₃NO₁₅

Molecular Weight

1018.4 g/mol

InChI Key

YAVZHCFFUATPRK-YZPBMOCRSA-N

FDA UNII

LXW024X05M

Erythromycin Stearate is the stearate salt form of erythromycin, a broad-spectrum, topical macrolide antibiotic with antibacterial activity. Erythromycin stearate diffuses through the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This prevents bacterial protein synthesis. Erythromycin stearate 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 Stearate

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;octadecanoic acid

2.1.2 InChI

InChI=1S/C37H67NO13.C18H36O2/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;1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;2-17H2,1H3,(H,19,20)/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;/m1./s1

2.1.3 InChI Key

YAVZHCFFUATPRK-YZPBMOCRSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCCCC(=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)O)(C)O)C)C)O)(C)O

2.1.5 Isomeric SMILES

CCCCCCCCCCCCCCCCCC(=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)O)(C)O)C)C)O)(C)O

2.2 Other Identifiers

2.2.1 UNII

LXW024X05M

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Gallimycin

2.3.2 Depositor-Supplied Synonyms

1. 643-22-1

2. Abboticine

3. Bristamycin

4. Erypar

5. Dowmycin E

6. Wyamycin S

7. Pfizer-e

8. Erythrocin Stearate

9. Gallimycin

10. Sk-erythromycin

11. Erythromycin Octadecanoate (salt)

12. Nsc-756747

13. Nci-c55674

14. Lxw024x05m

15. Eratrex

16. Meberyt

17. Qidmycin

18. Ethril

19. Ethril 250

20. Ethril 500

21. Erythromycin Stearate (salt)

22. Erythromycin, Stearate (salt)

23. Erythromycin Steraric Acid Salt

24. Ccris 1504

25. Oe 7

26. Hsdb 4178

27. Einecs 211-396-1

28. Unii-lxw024x05m

29. Stearic Acid, Compd. With Erythromycin (1:1)

30. Bristamycin (tn)

31. Octadecanoic Acid, Compd. With Erythromycin (1:1)

32. Erythromycini Stearas

33. Erythromycin Stearate [usp:ban:jan]

34. Chembl1200510

35. Chebi:34742

36. Hms501d19

37. Erythromycin Stearate [mi]

38. Erythromycin Stearate/ >550ug/mg

39. Hms3264b08

40. Pharmakon1600-01500281

41. Erythromycin Stearate (jp17/usp)

42. Erythromycin Stearate [jan]

43. Erythromycin Stearate [hsdb]

44. Ccg-39117

45. Erythromycin Stearate [vandf]

46. Mfcd00084690

47. Nsc756747

48. Erythromycin Stearate [mart.]

49. Erythromycin Stearate [usp-rs]

50. Erythromycin Stearate [who-dd]

51. Erythromycin Stearate [who-ip]

52. Nsc 756747

53. Ncgc00180891-01

54. Erythromycin Stearate [orange Book]

55. Sbi-0207065.p001

56. Erythromycin Stearate [usp Impurity]

57. Hy-108875

58. Cs-0031206

59. Erythromycin Stearate [usp Monograph]

60. Erythromycini Stearas [who-ip Latin]

61. D02184

62. Erythromycin Stearate For Impurity S Identification

63. Sr-01000872741

64. Sr-01000872741-1

65. W-104851

66. Q27283244

67. Erythromycin Stearate, Antibiotic For Culture Media Use Only

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₅₅H₁₀₃NO₁₅
Molecular Weight	1018.4 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	23
Exact Mass	1017.73277158 g/mol
Monoisotopic Mass	1017.73277158 g/mol
Topological Polar Surface Area	231 Å²
Heavy Atom Count	71
Formal Charge	0
Complexity	1380
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 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Erythrocin stearate
Drug Label	ERYTHROCIN STEARATE Filmtab tablets (erythromycin stearate tablets, USP) are an antibacterial product containing the stearate salt of erythromycin in a unique film coating.Erythromycin is produced by a strain of Saccharopolyspora erythraea (formerly...
Active Ingredient	Erythromycin stearate
Dosage Form	Tablet
Route	Oral
Strength	eq 250mg base
Market Status	Prescription
Company	Arbor Pharms

2 of 2
Drug Name	Erythrocin stearate
Drug Label	ERYTHROCIN STEARATE Filmtab tablets (erythromycin stearate tablets, USP) are an antibacterial product containing the stearate salt of erythromycin in a unique film coating.Erythromycin is produced by a strain of Saccharopolyspora erythraea (formerly...
Active Ingredient	Erythromycin stearate
Dosage Form	Tablet
Route	Oral
Strength	eq 250mg base
Market Status	Prescription
Company	Arbor Pharms

4.2 Therapeutic Uses

ITS ACTIONS & USES ARE IDENTICAL TO THOSE OF ERYTHROMYCIN.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1124

ERYTHROMYCIN MAY BE USEFUL FOR DISSEMINATED GONOCOCCAL DISEASE IN PREGNANT PT WHO IS ALLERGIC TO PENICILLIN... 13 PT...TREATED WITH 500 MG OF ERYTHROMYCIN... STEARATE, GIVEN ORALLY EVERY 6 HR FOR 5 DAYS, SHOWED RAPID CLINICAL & BACTERIOLOGICAL RESPONSES.

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. 1225

ANTIBACTERIAL AGENT

MEDICATION (VET): ANTIBACTERIAL AGENT

4.3 Drug Warning

...ERYTHROMYCIN & ITS DERIV SELDOM CAUSE SERIOUS ADVERSE REACTIONS.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 1258

5 Pharmacology and Biochemistry

5.1 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.)

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

PEAK CONCN IN PLASMA...0.3-0.5 UG/ML 4 HR AFTER ORAL ADMIN OF 250 MG OF BASE & ARE 0.3-1.9 UG/ML AFTER...500-MG TABLET. VARIOUS ESTERS OF ERYTHROMYCIN HAVE BEEN PREPARED TO...IMPROVE STABILITY & FACILITATE ABSORPTION. ...CONCN OF ERYTHROMYCIN IN PLASMA ARE LITTLE DIFFERENT IF STEARATE IS GIVEN ORALLY.

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

...DIFFUSES READILY INTO INTRACELLULAR FLUIDS, & ANTIBACTERIAL ACTIVITY... ACHIEVED AT...ALL SITES EXCEPT BRAIN & CSF. ...ONE OF FEW ANTIBIOTICS THAT PENETRATES INTO PROSTATIC FLUID, CONCN ARE APPROX 40% OF...PLASMA. EXTENT OF BINDING...TO PLASMA PROTEINS VARIES...PROBABLY EXCEEDS 70% IN ALL.../FORMS OF DRUG/. /ERYTHROMYCIN/

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

ERYTHROMYCIN BASE IS ADEQUATELY ABSORBED FROM UPPER PART OF SMALL INTESTINE; IT IS INACTIVATED BY GASTRIC JUICE... FOOD IN STOMACH DELAYS ITS ULTIMATE ABSORPTION. /ERYTHROMYCIN/

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

ERYTHROMYCIN TRAVERSES PLACENTAL BARRIER; & CONCN OF DRUG IN FETAL PLASMA ARE ABOUT 5-20% OF THOSE IN MATERNAL CIRCULATION. /ERYTHROMYCIN/

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

For more Absorption, Distribution and Excretion (Complete) data for ERYTHROMYCIN STEARATE (11 total), please visit the HSDB record page.

5.4 Metabolism/Metabolites

IT IS HYDROLYZED IN SMALL INTESTINE & IN TISSUES TO YIELD ERYTHROMYCIN.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1124

5.5 Mechanism of Action

...INHIBIT PROTEIN SYNTH BY BINDING TO 50 S RIBOSOMAL SUBUNITS OF SENSITIVE MICROORGANISMS. ... ASSOC BETWEEN ERYTHROMYCIN & RIBOSOME IS REVERSIBLE BUT TAKES PLACE ONLY WHEN 50 S SUBUNIT IS FREE FROM TRNA MOLECULES BEARING NASCENT PEPTIDE CHAINS. PRODN...OF HIGHLY POLYMERIZED HOMOPEPTIDES IS SUPPRESSED. /ERYTHROMYCIN/

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

THE NONIONIZED FORM OF THE DRUG IS CONSIDERABLY MORE PERMEABLE TO CELLS, & THIS PROBABLY EXPLAINS INCREASED ANTIMICROBIAL ACTIVITY THAT IS OBSERVED AT ALKALINE PH. /ERYTHROMYCIN/

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

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